NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	272.628
LogP:	2.99
LogD:	3.07
LogS:	-3.457
# Rotatable Bonds:	6
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.786
Synthetic Accessibility Score:	2.299
Fsp3:	0.333
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:	-4.563
MDCK Permeability:	1.604453063919209e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.088
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.035
30% Bioavailability (F30%):	0.371

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.951
Plasma Protein Binding (PPB):	89.64214324951172%
Volume Distribution (VD):	2.031
Pgp-substrate:	7.196589469909668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.818
CYP2C19-inhibitor:	0.645
CYP2C19-substrate:	0.721
CYP2C9-inhibitor:	0.126
CYP2C9-substrate:	0.895
CYP2D6-inhibitor:	0.048
CYP2D6-substrate:	0.863
CYP3A4-inhibitor:	0.171
CYP3A4-substrate:	0.476

ADMET: Excretion

Clearance (CL):	11.541
Half-life (T1/2):	0.797

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.878
Drug-inuced Liver Injury (DILI):	0.698
AMES Toxicity:	0.142
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.868
Carcinogencity:	0.55
Eye Corrosion:	0.008
Eye Irritation:	0.75
Respiratory Toxicity:	0.034

Download Data

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

Natural Product: NPC55300

Natural Product ID:	NPC55300
*Common Name:**	(E)-3-[3-Methoxy-4-(3-Methylbut-2-Enoxy)Phenyl]Prop-2-En-1-Ol
IUPAC Name:	(E)-3-[3-methoxy-4-(3-methylbut-2-enoxy)phenyl]prop-2-en-1-ol
Synonyms:
Standard InCHIKey:	JVHWAXVDBZHERR-SNAWJCMRSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-12(2)8-10-18-14-7-6-13(5-4-9-16)11-15(14)17-3/h4-8,11,16H,9-10H2,1-3H3/b5-4+
SMILES:	OC/C=C/c1ccc(c(c1)OC)OCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252116
PubChem CID:	10220553
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
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	fruit	Lanyu Island, Taitung County, Taiwan	n.a.	PMID[10395498]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17822293]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2740	Cell Line	Neutrophils		IC50	>	100000.0	nM	PMID[524212]

☑ 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 NPC55300 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	293
0.1-0.2	1827
0.2-0.3	6389
0.3-0.4	13192
0.4-0.5	3931
0.5-0.6	7124
0.6-0.7	7314
0.7-0.8	2216
0.8-0.85	318
0.85-0.9	78
0.9-0.95	11
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9904	High Similarity	NPC165646
0.9612	High Similarity	NPC258171
0.9612	High Similarity	NPC227894
0.934	High Similarity	NPC137685
0.9252	High Similarity	NPC78918
0.9252	High Similarity	NPC139617
0.9126	High Similarity	NPC310905
0.9126	High Similarity	NPC51633
0.9126	High Similarity	NPC12714
0.9115	High Similarity	NPC199023
0.9107	High Similarity	NPC37858
0.9065	High Similarity	NPC7097
0.9065	High Similarity	NPC233731
0.9065	High Similarity	NPC246358
0.9065	High Similarity	NPC36108
0.9038	High Similarity	NPC192596
0.8952	High Similarity	NPC292792
0.8929	High Similarity	NPC164386
0.8899	High Similarity	NPC156840
0.8899	High Similarity	NPC257124
0.8899	High Similarity	NPC8547
0.8899	High Similarity	NPC173746
0.8899	High Similarity	NPC245552
0.887	High Similarity	NPC290451
0.887	High Similarity	NPC127389
0.885	High Similarity	NPC124916
0.8839	High Similarity	NPC221049
0.8807	High Similarity	NPC46844
0.8803	High Similarity	NPC109822
0.8803	High Similarity	NPC48990
0.8803	High Similarity	NPC114901
0.8803	High Similarity	NPC293701
0.8803	High Similarity	NPC94276
0.8793	High Similarity	NPC71090
0.8774	High Similarity	NPC38079
0.8774	High Similarity	NPC108875
0.8772	High Similarity	NPC24474
0.8772	High Similarity	NPC135961
0.8772	High Similarity	NPC311595
0.8761	High Similarity	NPC86947
0.8739	High Similarity	NPC303522
0.8729	High Similarity	NPC194519
0.8707	High Similarity	NPC470804
0.8692	High Similarity	NPC470393
0.8684	High Similarity	NPC474214
0.8684	High Similarity	NPC255675
0.8684	High Similarity	NPC159916
0.8684	High Similarity	NPC474040
0.8661	High Similarity	NPC294941
0.8655	High Similarity	NPC191037
0.8655	High Similarity	NPC178284
0.8655	High Similarity	NPC58607
0.8644	High Similarity	NPC74478
0.8636	High Similarity	NPC179309
0.8621	High Similarity	NPC204466
0.8621	High Similarity	NPC207613
0.8609	High Similarity	NPC474320
0.8609	High Similarity	NPC181969
0.8609	High Similarity	NPC320987
0.8596	High Similarity	NPC293619
0.8596	High Similarity	NPC280001
0.8596	High Similarity	NPC39793
0.8583	High Similarity	NPC183181
0.8583	High Similarity	NPC118787
0.8583	High Similarity	NPC319625
0.8583	High Similarity	NPC41706
0.8583	High Similarity	NPC111247
0.8583	High Similarity	NPC163332
0.8583	High Similarity	NPC147821
0.8583	High Similarity	NPC292056
0.8559	High Similarity	NPC203924
0.8559	High Similarity	NPC195873
0.8547	High Similarity	NPC473853
0.8547	High Similarity	NPC262156
0.8547	High Similarity	NPC113865
0.8547	High Similarity	NPC184651
0.8547	High Similarity	NPC476343
0.8547	High Similarity	NPC324571
0.8547	High Similarity	NPC470212
0.8547	High Similarity	NPC54872
0.8547	High Similarity	NPC70752
0.8547	High Similarity	NPC343720
0.8547	High Similarity	NPC312675
0.8545	High Similarity	NPC127326
0.8534	High Similarity	NPC229401
0.8534	High Similarity	NPC35071
0.8534	High Similarity	NPC177475
0.8534	High Similarity	NPC148615
0.8534	High Similarity	NPC202474
0.8522	High Similarity	NPC63083
0.8522	High Similarity	NPC470626
0.8519	High Similarity	NPC8302
0.8475	Intermediate Similarity	NPC85488
0.8475	Intermediate Similarity	NPC270326
0.8475	Intermediate Similarity	NPC209567
0.8462	Intermediate Similarity	NPC267064
0.8448	Intermediate Similarity	NPC310338
0.8448	Intermediate Similarity	NPC281298
0.8443	Intermediate Similarity	NPC210623
0.8443	Intermediate Similarity	NPC248355
0.8443	Intermediate Similarity	NPC166040
0.8443	Intermediate Similarity	NPC285339
0.8443	Intermediate Similarity	NPC218856
0.8443	Intermediate Similarity	NPC273295
0.8443	Intermediate Similarity	NPC202582
0.8443	Intermediate Similarity	NPC226788
0.8443	Intermediate Similarity	NPC222004
0.8443	Intermediate Similarity	NPC3439
0.8443	Intermediate Similarity	NPC470258
0.8443	Intermediate Similarity	NPC5851
0.8443	Intermediate Similarity	NPC86030
0.8443	Intermediate Similarity	NPC190629
0.8435	Intermediate Similarity	NPC259638
0.843	Intermediate Similarity	NPC474119
0.8426	Intermediate Similarity	NPC474603
0.8426	Intermediate Similarity	NPC12987
0.8417	Intermediate Similarity	NPC87113
0.8407	Intermediate Similarity	NPC204120
0.8407	Intermediate Similarity	NPC165106
0.8403	Intermediate Similarity	NPC317769
0.8403	Intermediate Similarity	NPC280704
0.8403	Intermediate Similarity	NPC31344
0.8403	Intermediate Similarity	NPC471693
0.8396	Intermediate Similarity	NPC471576
0.8396	Intermediate Similarity	NPC100870
0.839	Intermediate Similarity	NPC49341
0.8378	Intermediate Similarity	NPC165386
0.8376	Intermediate Similarity	NPC227217
0.8376	Intermediate Similarity	NPC117780
0.8376	Intermediate Similarity	NPC56214
0.8376	Intermediate Similarity	NPC95614
0.8376	Intermediate Similarity	NPC474565
0.8376	Intermediate Similarity	NPC2058
0.8376	Intermediate Similarity	NPC165133
0.8376	Intermediate Similarity	NPC232316
0.8376	Intermediate Similarity	NPC242885
0.8374	Intermediate Similarity	NPC472338
0.8364	Intermediate Similarity	NPC194034
0.8362	Intermediate Similarity	NPC164706
0.8362	Intermediate Similarity	NPC277460
0.8362	Intermediate Similarity	NPC272471
0.8362	Intermediate Similarity	NPC137537
0.8362	Intermediate Similarity	NPC107588
0.8362	Intermediate Similarity	NPC70744
0.8361	Intermediate Similarity	NPC72529
0.8361	Intermediate Similarity	NPC302378
0.8348	Intermediate Similarity	NPC81067
0.8348	Intermediate Similarity	NPC290470
0.8348	Intermediate Similarity	NPC9341
0.8348	Intermediate Similarity	NPC154256
0.8348	Intermediate Similarity	NPC193067
0.8347	Intermediate Similarity	NPC304630
0.8347	Intermediate Similarity	NPC17837
0.8333	Intermediate Similarity	NPC305205
0.8333	Intermediate Similarity	NPC60517
0.8333	Intermediate Similarity	NPC246704
0.8333	Intermediate Similarity	NPC20443
0.8333	Intermediate Similarity	NPC146886
0.8319	Intermediate Similarity	NPC115379
0.8319	Intermediate Similarity	NPC261661
0.8306	Intermediate Similarity	NPC472597
0.8306	Intermediate Similarity	NPC469613
0.8306	Intermediate Similarity	NPC30043
0.8306	Intermediate Similarity	NPC469625
0.8305	Intermediate Similarity	NPC189844
0.8305	Intermediate Similarity	NPC109083
0.8305	Intermediate Similarity	NPC472596
0.8305	Intermediate Similarity	NPC269843
0.8305	Intermediate Similarity	NPC60962
0.8305	Intermediate Similarity	NPC224814
0.8305	Intermediate Similarity	NPC14007
0.8305	Intermediate Similarity	NPC158949
0.8305	Intermediate Similarity	NPC166759
0.8304	Intermediate Similarity	NPC31279
0.8293	Intermediate Similarity	NPC270849
0.8293	Intermediate Similarity	NPC26653
0.8291	Intermediate Similarity	NPC163036
0.8291	Intermediate Similarity	NPC299406
0.8291	Intermediate Similarity	NPC20674
0.8288	Intermediate Similarity	NPC75440
0.8279	Intermediate Similarity	NPC210355
0.8264	Intermediate Similarity	NPC289459
0.8264	Intermediate Similarity	NPC27352
0.8264	Intermediate Similarity	NPC148627
0.8264	Intermediate Similarity	NPC280767
0.8261	Intermediate Similarity	NPC475815
0.8261	Intermediate Similarity	NPC47194
0.8261	Intermediate Similarity	NPC473264
0.825	Intermediate Similarity	NPC244876
0.825	Intermediate Similarity	NPC21238
0.825	Intermediate Similarity	NPC279379
0.825	Intermediate Similarity	NPC220598
0.825	Intermediate Similarity	NPC108545
0.825	Intermediate Similarity	NPC165375
0.8246	Intermediate Similarity	NPC301735
0.824	Intermediate Similarity	NPC160991
0.824	Intermediate Similarity	NPC16208
0.824	Intermediate Similarity	NPC7903
0.824	Intermediate Similarity	NPC5423
0.824	Intermediate Similarity	NPC35932

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 NPC55300 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	1050
0.2-0.3	1868
0.3-0.4	2631
0.4-0.5	1626
0.5-0.6	964
0.6-0.7	590
0.7-0.8	140
0.8-0.85	7
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8899	High Similarity	NPD228	Approved
0.8796	High Similarity	NPD2684	Approved
0.8772	High Similarity	NPD1357	Approved
0.8482	Intermediate Similarity	NPD7843	Approved
0.8421	Intermediate Similarity	NPD7157	Approved
0.8407	Intermediate Similarity	NPD5283	Phase 1
0.8364	Intermediate Similarity	NPD290	Approved
0.8241	Intermediate Similarity	NPD291	Approved
0.812	Intermediate Similarity	NPD5536	Phase 2
0.8099	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD9365	Approved
0.8036	Intermediate Similarity	NPD1358	Approved
0.8016	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD821	Approved
0.8	Intermediate Similarity	NPD3027	Phase 3
0.7946	Intermediate Similarity	NPD968	Approved
0.7934	Intermediate Similarity	NPD3705	Approved
0.792	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD9296	Approved
0.784	Intermediate Similarity	NPD9494	Approved
0.7812	Intermediate Similarity	NPD1613	Approved
0.7812	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD2983	Phase 2
0.7805	Intermediate Similarity	NPD2982	Phase 2
0.7797	Intermediate Similarity	NPD6671	Approved
0.7788	Intermediate Similarity	NPD3134	Approved
0.7769	Intermediate Similarity	NPD5846	Approved
0.7769	Intermediate Similarity	NPD6516	Phase 2
0.7739	Intermediate Similarity	NPD556	Approved
0.7724	Intermediate Similarity	NPD2981	Phase 2
0.7705	Intermediate Similarity	NPD3496	Discontinued
0.7674	Intermediate Similarity	NPD3620	Phase 2
0.7674	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD1558	Phase 1
0.7656	Intermediate Similarity	NPD3145	Approved
0.7656	Intermediate Similarity	NPD3144	Approved
0.7652	Intermediate Similarity	NPD2161	Phase 2
0.7638	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD1778	Approved
0.7619	Intermediate Similarity	NPD6584	Phase 3
0.7612	Intermediate Similarity	NPD4162	Approved
0.7603	Intermediate Similarity	NPD1182	Approved
0.7597	Intermediate Similarity	NPD2674	Phase 3
0.7594	Intermediate Similarity	NPD1375	Discontinued
0.7581	Intermediate Similarity	NPD2235	Phase 2
0.7581	Intermediate Similarity	NPD2231	Phase 2
0.7559	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD3018	Phase 2
0.754	Intermediate Similarity	NPD1817	Approved
0.754	Intermediate Similarity	NPD1818	Approved
0.754	Intermediate Similarity	NPD1819	Approved
0.754	Intermediate Similarity	NPD1820	Approved
0.7538	Intermediate Similarity	NPD4060	Phase 1
0.7537	Intermediate Similarity	NPD7153	Discontinued
0.75	Intermediate Similarity	NPD776	Approved
0.75	Intermediate Similarity	NPD1091	Approved
0.748	Intermediate Similarity	NPD4626	Approved
0.7479	Intermediate Similarity	NPD1241	Discontinued
0.746	Intermediate Similarity	NPD8651	Approved
0.7459	Intermediate Similarity	NPD1548	Phase 1
0.7444	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3021	Approved
0.7436	Intermediate Similarity	NPD3022	Approved
0.7426	Intermediate Similarity	NPD4110	Phase 3
0.7426	Intermediate Similarity	NPD6331	Phase 2
0.7426	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD2861	Phase 2
0.7398	Intermediate Similarity	NPD5585	Approved
0.7398	Intermediate Similarity	NPD5691	Approved
0.7395	Intermediate Similarity	NPD5535	Approved
0.7381	Intermediate Similarity	NPD3685	Discontinued
0.7381	Intermediate Similarity	NPD5327	Phase 3
0.7381	Intermediate Similarity	NPD6583	Phase 3
0.7381	Intermediate Similarity	NPD6582	Phase 2
0.736	Intermediate Similarity	NPD1610	Phase 2
0.7353	Intermediate Similarity	NPD4236	Phase 3
0.7353	Intermediate Similarity	NPD4237	Approved
0.7353	Intermediate Similarity	NPD3060	Approved
0.7348	Intermediate Similarity	NPD5735	Approved
0.7348	Intermediate Similarity	NPD447	Suspended
0.7344	Intermediate Similarity	NPD3690	Phase 2
0.7344	Intermediate Similarity	NPD3691	Phase 2
0.7338	Intermediate Similarity	NPD4123	Phase 3
0.7333	Intermediate Similarity	NPD111	Approved
0.7323	Intermediate Similarity	NPD2922	Phase 1
0.7308	Intermediate Similarity	NPD3165	Approved
0.7308	Intermediate Similarity	NPD3166	Approved
0.7308	Intermediate Similarity	NPD3167	Approved
0.7308	Intermediate Similarity	NPD3179	Approved
0.7308	Intermediate Similarity	NPD7095	Approved
0.7308	Intermediate Similarity	NPD3164	Approved
0.7308	Intermediate Similarity	NPD3180	Approved
0.7305	Intermediate Similarity	NPD3686	Approved
0.7305	Intermediate Similarity	NPD3687	Approved
0.7304	Intermediate Similarity	NPD9501	Approved
0.7302	Intermediate Similarity	NPD1840	Phase 2
0.7295	Intermediate Similarity	NPD3596	Phase 2
0.7293	Intermediate Similarity	NPD2653	Approved
0.7293	Intermediate Similarity	NPD6653	Approved
0.7288	Intermediate Similarity	NPD5451	Approved
0.7286	Intermediate Similarity	NPD52	Approved
0.7286	Intermediate Similarity	NPD7526	Approved
0.7286	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4140	Approved
0.7266	Intermediate Similarity	NPD1794	Approved
0.7258	Intermediate Similarity	NPD1798	Approved
0.7258	Intermediate Similarity	NPD1797	Approved
0.7252	Intermediate Similarity	NPD5109	Approved
0.7252	Intermediate Similarity	NPD5111	Phase 2
0.7252	Intermediate Similarity	NPD5718	Phase 2
0.7252	Intermediate Similarity	NPD5110	Phase 2
0.7246	Intermediate Similarity	NPD5241	Discontinued
0.7244	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD4908	Phase 1
0.7222	Intermediate Similarity	NPD9295	Approved
0.7214	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD558	Phase 2
0.7207	Intermediate Similarity	NPD2933	Approved
0.7207	Intermediate Similarity	NPD2934	Approved
0.7207	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1423	Approved
0.7183	Intermediate Similarity	NPD1653	Approved
0.7177	Intermediate Similarity	NPD1894	Discontinued
0.7177	Intermediate Similarity	NPD6581	Approved
0.7177	Intermediate Similarity	NPD6580	Approved
0.7176	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1712	Approved
0.7154	Intermediate Similarity	NPD4993	Discontinued
0.7143	Intermediate Similarity	NPD1774	Approved
0.7143	Intermediate Similarity	NPD2860	Approved
0.7143	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD844	Approved
0.7143	Intermediate Similarity	NPD2859	Approved
0.7133	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD987	Approved
0.7121	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6798	Discontinued
0.712	Intermediate Similarity	NPD1651	Approved
0.712	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD9552	Approved
0.7113	Intermediate Similarity	NPD2122	Discontinued
0.7111	Intermediate Similarity	NPD4538	Approved
0.7111	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4536	Approved
0.7109	Intermediate Similarity	NPD1669	Approved
0.7109	Intermediate Similarity	NPD4359	Approved
0.7109	Intermediate Similarity	NPD4749	Approved
0.7105	Intermediate Similarity	NPD3020	Approved
0.7101	Intermediate Similarity	NPD6674	Discontinued
0.7101	Intermediate Similarity	NPD5177	Phase 3
0.7094	Intermediate Similarity	NPD9697	Approved
0.7092	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD3657	Discovery
0.709	Intermediate Similarity	NPD6355	Discontinued
0.7087	Intermediate Similarity	NPD422	Phase 1
0.7083	Intermediate Similarity	NPD4675	Approved
0.7083	Intermediate Similarity	NPD4678	Approved
0.7077	Intermediate Similarity	NPD5647	Approved
0.7073	Intermediate Similarity	NPD709	Approved
0.7073	Intermediate Similarity	NPD2557	Approved
0.7068	Intermediate Similarity	NPD6233	Phase 2
0.7068	Intermediate Similarity	NPD3532	Approved
0.7068	Intermediate Similarity	NPD3531	Approved
0.7068	Intermediate Similarity	NPD3530	Approved
0.7068	Intermediate Similarity	NPD4062	Phase 3
0.7068	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2667	Approved
0.7063	Intermediate Similarity	NPD2668	Approved
0.7059	Intermediate Similarity	NPD2154	Approved
0.7059	Intermediate Similarity	NPD2155	Approved
0.7059	Intermediate Similarity	NPD2156	Approved
0.7055	Intermediate Similarity	NPD5772	Approved
0.7055	Intermediate Similarity	NPD5773	Approved
0.7049	Intermediate Similarity	NPD592	Approved
0.7049	Intermediate Similarity	NPD594	Approved
0.7043	Intermediate Similarity	NPD1242	Phase 1
0.7037	Intermediate Similarity	NPD2157	Approved
0.7037	Intermediate Similarity	NPD6353	Approved
0.7031	Intermediate Similarity	NPD2230	Approved
0.7031	Intermediate Similarity	NPD1608	Approved
0.7031	Intermediate Similarity	NPD2233	Approved
0.7031	Intermediate Similarity	NPD2232	Approved
0.7021	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2560	Approved
0.7007	Intermediate Similarity	NPD2563	Approved
0.7	Intermediate Similarity	NPD2677	Approved
0.6992	Remote Similarity	NPD1048	Approved
0.6985	Remote Similarity	NPD6896	Approved
0.6985	Remote Similarity	NPD6895	Approved
0.6984	Remote Similarity	NPD3443	Approved
0.6984	Remote Similarity	NPD3445	Approved
0.6984	Remote Similarity	NPD3444	Approved
0.6978	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3688	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