NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.11
Volume:	238.036
LogP:	3.394
LogD:	3.23
LogS:	-3.514
# Rotatable Bonds:	6
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.471
Synthetic Accessibility Score:	2.104
Fsp3:	0.308
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:	-4.642
MDCK Permeability:	2.7294114261167124e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.045
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.357
Plasma Protein Binding (PPB):	96.14630126953125%
Volume Distribution (VD):	0.576
Pgp-substrate:	2.8753368854522705%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.816
CYP2C19-inhibitor:	0.931
CYP2C19-substrate:	0.214
CYP2C9-inhibitor:	0.621
CYP2C9-substrate:	0.855
CYP2D6-inhibitor:	0.853
CYP2D6-substrate:	0.873
CYP3A4-inhibitor:	0.461
CYP3A4-substrate:	0.175

ADMET: Excretion

Clearance (CL):	11.023
Half-life (T1/2):	0.927

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.038
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.062
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.904
Carcinogencity:	0.372
Eye Corrosion:	0.213
Eye Irritation:	0.974
Respiratory Toxicity:	0.128

Download Data

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

Natural Product: NPC328459

Natural Product ID:	NPC328459
*Common Name:**	[(Z)-Hex-3-Enyl] 2-Hydroxybenzoate
IUPAC Name:	[(Z)-hex-3-enyl] 2-hydroxybenzoate
Synonyms:
Standard InCHIKey:	IEPWIPZLLIOZLU-ARJAWSKDSA-N
Standard InCHI:	InChI=1S/C13H16O3/c1-2-3-4-7-10-16-13(15)11-8-5-6-9-12(11)14/h3-6,8-9,14H,2,7,10H2,1H3/b4-3-
SMILES:	CC/C=CCCOC(=O)c1ccccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1897308
PubChem CID:	5371102
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters [CHEMONTID:0004700] o-Hydroxybenzoic acid esters

*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

☑ 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
Potency	6

Activity Type	# Activity
Individual Protein	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[455748]
NPT2	Others	Unspecified		Potency	n.a.	216.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48557.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	86349.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	5494.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24336.5	nM	PubChem BioAssay data set

☑ 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 NPC328459 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	252
0.1-0.2	1413
0.2-0.3	4251
0.3-0.4	9784
0.4-0.5	8908
0.5-0.6	5146
0.6-0.7	9058
0.7-0.8	3599
0.8-0.85	231
0.85-0.9	45
0.9-0.95	4
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC90522
0.9911	High Similarity	NPC72977
0.991	High Similarity	NPC94637
0.973	High Similarity	NPC128825
0.9561	High Similarity	NPC233282
0.9244	High Similarity	NPC4164
0.913	High Similarity	NPC217423
0.9009	High Similarity	NPC100551
0.8992	High Similarity	NPC311219
0.8957	High Similarity	NPC188907
0.8947	High Similarity	NPC211421
0.8852	High Similarity	NPC95309
0.8843	High Similarity	NPC265910
0.8843	High Similarity	NPC91475
0.881	High Similarity	NPC43627
0.881	High Similarity	NPC289572
0.881	High Similarity	NPC157478
0.881	High Similarity	NPC200422
0.881	High Similarity	NPC295406
0.88	High Similarity	NPC7012
0.878	High Similarity	NPC71525
0.874	High Similarity	NPC474097
0.8739	High Similarity	NPC230951
0.8729	High Similarity	NPC94298
0.8729	High Similarity	NPC27633
0.872	High Similarity	NPC12694
0.8707	High Similarity	NPC81808
0.8689	High Similarity	NPC184219
0.8689	High Similarity	NPC6888
0.8673	High Similarity	NPC224584
0.8672	High Similarity	NPC29317
0.8672	High Similarity	NPC176102
0.8672	High Similarity	NPC267539
0.8672	High Similarity	NPC229638
0.8672	High Similarity	NPC254832
0.8672	High Similarity	NPC204257
0.8672	High Similarity	NPC71108
0.8651	High Similarity	NPC214702
0.8651	High Similarity	NPC470831
0.8644	High Similarity	NPC45104
0.8644	High Similarity	NPC125252
0.8629	High Similarity	NPC181715
0.8584	High Similarity	NPC303264
0.8571	High Similarity	NPC307732
0.8571	High Similarity	NPC42292
0.8559	High Similarity	NPC131192
0.8527	High Similarity	NPC142027
0.8527	High Similarity	NPC27407
0.8525	High Similarity	NPC67300
0.8512	High Similarity	NPC272454
0.8512	High Similarity	NPC35856
0.8512	High Similarity	NPC26433
0.8512	High Similarity	NPC301987
0.8512	High Similarity	NPC159760
0.8512	High Similarity	NPC222876
0.8512	High Similarity	NPC179092
0.8512	High Similarity	NPC292665
0.8512	High Similarity	NPC115188
0.8512	High Similarity	NPC244994
0.8512	High Similarity	NPC178395
0.85	High Similarity	NPC233165
0.85	High Similarity	NPC184579
0.8492	Intermediate Similarity	NPC238309
0.8468	Intermediate Similarity	NPC287473
0.8468	Intermediate Similarity	NPC167055
0.8468	Intermediate Similarity	NPC240744
0.8462	Intermediate Similarity	NPC223004
0.8462	Intermediate Similarity	NPC53953
0.8438	Intermediate Similarity	NPC470160
0.8413	Intermediate Similarity	NPC293453
0.8403	Intermediate Similarity	NPC312800
0.839	Intermediate Similarity	NPC118288
0.839	Intermediate Similarity	NPC276111
0.8387	Intermediate Similarity	NPC4012
0.8387	Intermediate Similarity	NPC193805
0.8374	Intermediate Similarity	NPC132518
0.8374	Intermediate Similarity	NPC46634
0.8374	Intermediate Similarity	NPC477151
0.8374	Intermediate Similarity	NPC217756
0.8372	Intermediate Similarity	NPC472591
0.8372	Intermediate Similarity	NPC153783
0.8359	Intermediate Similarity	NPC198249
0.8346	Intermediate Similarity	NPC78662
0.8346	Intermediate Similarity	NPC8005
0.8333	Intermediate Similarity	NPC121259
0.8333	Intermediate Similarity	NPC240664
0.8333	Intermediate Similarity	NPC478200
0.8333	Intermediate Similarity	NPC264428
0.8333	Intermediate Similarity	NPC33144
0.8321	Intermediate Similarity	NPC291454
0.832	Intermediate Similarity	NPC49938
0.8284	Intermediate Similarity	NPC478201
0.8284	Intermediate Similarity	NPC472035
0.8279	Intermediate Similarity	NPC470092
0.8279	Intermediate Similarity	NPC474874
0.8271	Intermediate Similarity	NPC52358
0.8271	Intermediate Similarity	NPC19622
0.8271	Intermediate Similarity	NPC112789
0.8268	Intermediate Similarity	NPC186098
0.8268	Intermediate Similarity	NPC80694
0.8268	Intermediate Similarity	NPC473744
0.8264	Intermediate Similarity	NPC41567
0.8264	Intermediate Similarity	NPC241089
0.8258	Intermediate Similarity	NPC71256
0.8258	Intermediate Similarity	NPC70380
0.8254	Intermediate Similarity	NPC204579
0.8254	Intermediate Similarity	NPC110211
0.824	Intermediate Similarity	NPC470163
0.824	Intermediate Similarity	NPC470162
0.824	Intermediate Similarity	NPC117794
0.824	Intermediate Similarity	NPC221798
0.8235	Intermediate Similarity	NPC41851
0.823	Intermediate Similarity	NPC304638
0.8226	Intermediate Similarity	NPC69403
0.8226	Intermediate Similarity	NPC291189
0.8226	Intermediate Similarity	NPC244351
0.822	Intermediate Similarity	NPC17693
0.8217	Intermediate Similarity	NPC219892
0.8217	Intermediate Similarity	NPC189823
0.8211	Intermediate Similarity	NPC165197
0.8209	Intermediate Similarity	NPC158472
0.8209	Intermediate Similarity	NPC275903
0.8205	Intermediate Similarity	NPC476003
0.8203	Intermediate Similarity	NPC187907
0.8198	Intermediate Similarity	NPC35448
0.8198	Intermediate Similarity	NPC78701
0.8197	Intermediate Similarity	NPC61779
0.8197	Intermediate Similarity	NPC161617
0.8195	Intermediate Similarity	NPC212693
0.8195	Intermediate Similarity	NPC126739
0.8195	Intermediate Similarity	NPC94248
0.8195	Intermediate Similarity	NPC191835
0.8195	Intermediate Similarity	NPC197666
0.8195	Intermediate Similarity	NPC221104
0.819	Intermediate Similarity	NPC31274
0.8189	Intermediate Similarity	NPC293387
0.8182	Intermediate Similarity	NPC269414
0.8182	Intermediate Similarity	NPC160199
0.8182	Intermediate Similarity	NPC235115
0.8175	Intermediate Similarity	NPC472592
0.8167	Intermediate Similarity	NPC161304
0.8167	Intermediate Similarity	NPC240163
0.816	Intermediate Similarity	NPC477152
0.816	Intermediate Similarity	NPC477153
0.8154	Intermediate Similarity	NPC302844
0.8151	Intermediate Similarity	NPC474363
0.8151	Intermediate Similarity	NPC279916
0.8148	Intermediate Similarity	NPC470842
0.8148	Intermediate Similarity	NPC130485
0.8148	Intermediate Similarity	NPC313123
0.8148	Intermediate Similarity	NPC478217
0.8148	Intermediate Similarity	NPC158634
0.8145	Intermediate Similarity	NPC25168
0.8145	Intermediate Similarity	NPC198336
0.8136	Intermediate Similarity	NPC114682
0.8134	Intermediate Similarity	NPC295339
0.8134	Intermediate Similarity	NPC32360
0.8134	Intermediate Similarity	NPC139634
0.8134	Intermediate Similarity	NPC105456
0.813	Intermediate Similarity	NPC31314
0.813	Intermediate Similarity	NPC193193
0.813	Intermediate Similarity	NPC260837
0.813	Intermediate Similarity	NPC294964
0.8125	Intermediate Similarity	NPC2596
0.8125	Intermediate Similarity	NPC146351
0.812	Intermediate Similarity	NPC240593
0.812	Intermediate Similarity	NPC135837
0.812	Intermediate Similarity	NPC261292
0.812	Intermediate Similarity	NPC301915
0.812	Intermediate Similarity	NPC471954
0.812	Intermediate Similarity	NPC75272
0.8115	Intermediate Similarity	NPC273282
0.8115	Intermediate Similarity	NPC184527
0.8115	Intermediate Similarity	NPC474890
0.8115	Intermediate Similarity	NPC161943
0.8115	Intermediate Similarity	NPC283844
0.8108	Intermediate Similarity	NPC276775
0.8108	Intermediate Similarity	NPC92754
0.8108	Intermediate Similarity	NPC249912
0.8106	Intermediate Similarity	NPC164136
0.8103	Intermediate Similarity	NPC141523
0.8102	Intermediate Similarity	NPC126882
0.8102	Intermediate Similarity	NPC210966
0.8102	Intermediate Similarity	NPC478203
0.8099	Intermediate Similarity	NPC128249
0.8099	Intermediate Similarity	NPC477453
0.8099	Intermediate Similarity	NPC33717
0.8092	Intermediate Similarity	NPC203817
0.8092	Intermediate Similarity	NPC287533
0.8088	Intermediate Similarity	NPC474385
0.8087	Intermediate Similarity	NPC227255
0.8083	Intermediate Similarity	NPC163154
0.808	Intermediate Similarity	NPC283514
0.808	Intermediate Similarity	NPC297193
0.808	Intermediate Similarity	NPC325301
0.808	Intermediate Similarity	NPC309765
0.8077	Intermediate Similarity	NPC473777
0.807	Intermediate Similarity	NPC474365
0.807	Intermediate Similarity	NPC13426
0.807	Intermediate Similarity	NPC301943

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 NPC328459 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	902
0.2-0.3	1503
0.3-0.4	2639
0.4-0.5	2020
0.5-0.6	1228
0.6-0.7	507
0.7-0.8	104
0.8-0.85	10
0.85-0.9	8
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.973	High Similarity	NPD9493	Approved
0.9009	High Similarity	NPD74	Approved
0.9009	High Similarity	NPD9266	Approved
0.8992	High Similarity	NPD9717	Approved
0.8919	High Similarity	NPD9264	Approved
0.8919	High Similarity	NPD9267	Approved
0.8919	High Similarity	NPD9263	Approved
0.877	High Similarity	NPD1203	Approved
0.8729	High Similarity	NPD9545	Approved
0.8559	High Similarity	NPD9261	Approved
0.8413	Intermediate Similarity	NPD6832	Phase 2
0.84	Intermediate Similarity	NPD1019	Discontinued
0.839	Intermediate Similarity	NPD9281	Approved
0.8281	Intermediate Similarity	NPD411	Approved
0.8258	Intermediate Similarity	NPD2935	Discontinued
0.8258	Intermediate Similarity	NPD1551	Phase 2
0.8231	Intermediate Similarity	NPD447	Suspended
0.8217	Intermediate Similarity	NPD520	Approved
0.8031	Intermediate Similarity	NPD1164	Approved
0.8015	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD1240	Approved
0.7955	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1607	Approved
0.7891	Intermediate Similarity	NPD2797	Approved
0.7868	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD2798	Approved
0.782	Intermediate Similarity	NPD230	Phase 1
0.782	Intermediate Similarity	NPD1933	Approved
0.7807	Intermediate Similarity	NPD1238	Approved
0.7805	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1510	Phase 2
0.7778	Intermediate Similarity	NPD2799	Discontinued
0.7737	Intermediate Similarity	NPD1549	Phase 2
0.7727	Intermediate Similarity	NPD2313	Discontinued
0.7714	Intermediate Similarity	NPD6799	Approved
0.7664	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4308	Phase 3
0.7603	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD3268	Approved
0.7586	Intermediate Similarity	NPD7411	Suspended
0.7583	Intermediate Similarity	NPD2182	Approved
0.7568	Intermediate Similarity	NPD9258	Approved
0.7568	Intermediate Similarity	NPD9256	Approved
0.7563	Intermediate Similarity	NPD3134	Approved
0.7561	Intermediate Similarity	NPD1241	Discontinued
0.7559	Intermediate Similarity	NPD1778	Approved
0.7554	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD1358	Approved
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7464	Intermediate Similarity	NPD2796	Approved
0.7463	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD3764	Approved
0.745	Intermediate Similarity	NPD7075	Discontinued
0.7442	Intermediate Similarity	NPD422	Phase 1
0.7442	Intermediate Similarity	NPD1201	Approved
0.7413	Intermediate Similarity	NPD2532	Approved
0.7413	Intermediate Similarity	NPD2534	Approved
0.7413	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD2533	Approved
0.7413	Intermediate Similarity	NPD5401	Approved
0.741	Intermediate Similarity	NPD2346	Discontinued
0.741	Intermediate Similarity	NPD2344	Approved
0.7405	Intermediate Similarity	NPD3225	Approved
0.7402	Intermediate Similarity	NPD1759	Phase 1
0.7397	Intermediate Similarity	NPD6599	Discontinued
0.7395	Intermediate Similarity	NPD164	Approved
0.7376	Intermediate Similarity	NPD3750	Approved
0.7368	Intermediate Similarity	NPD9494	Approved
0.7365	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7819	Suspended
0.7364	Intermediate Similarity	NPD3496	Discontinued
0.7353	Intermediate Similarity	NPD4307	Phase 2
0.7348	Intermediate Similarity	NPD1470	Approved
0.7344	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5405	Approved
0.7338	Intermediate Similarity	NPD5406	Approved
0.7338	Intermediate Similarity	NPD5408	Approved
0.7338	Intermediate Similarity	NPD5404	Approved
0.7333	Intermediate Similarity	NPD9697	Approved
0.7323	Intermediate Similarity	NPD1758	Phase 1
0.7297	Intermediate Similarity	NPD6801	Discontinued
0.7292	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4380	Phase 2
0.7266	Intermediate Similarity	NPD7033	Discontinued
0.7266	Intermediate Similarity	NPD1894	Discontinued
0.7254	Intermediate Similarity	NPD7003	Approved
0.7254	Intermediate Similarity	NPD4628	Phase 3
0.7252	Intermediate Similarity	NPD1481	Phase 2
0.7226	Intermediate Similarity	NPD943	Approved
0.7222	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD3267	Approved
0.7218	Intermediate Similarity	NPD3266	Approved
0.7213	Intermediate Similarity	NPD290	Approved
0.7211	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD9257	Approved
0.7207	Intermediate Similarity	NPD9259	Approved
0.7206	Intermediate Similarity	NPD6798	Discontinued
0.7203	Intermediate Similarity	NPD2309	Approved
0.72	Intermediate Similarity	NPD5402	Approved
0.7194	Intermediate Similarity	NPD9279	Approved
0.7183	Intermediate Similarity	NPD1243	Approved
0.7176	Intermediate Similarity	NPD1535	Discovery
0.7164	Intermediate Similarity	NPD5647	Approved
0.7161	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD4626	Approved
0.7153	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3882	Suspended
0.7133	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1196	Approved
0.7133	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD9269	Phase 2
0.7121	Intermediate Similarity	NPD1608	Approved
0.7121	Intermediate Similarity	NPD3972	Approved
0.7119	Intermediate Similarity	NPD9495	Approved
0.7107	Intermediate Similarity	NPD1237	Approved
0.7105	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1511	Approved
0.7095	Intermediate Similarity	NPD3226	Approved
0.7086	Intermediate Similarity	NPD3817	Phase 2
0.7086	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD940	Approved
0.7083	Intermediate Similarity	NPD846	Approved
0.7077	Intermediate Similarity	NPD5691	Approved
0.7077	Intermediate Similarity	NPD9268	Approved
0.7075	Intermediate Similarity	NPD920	Approved
0.7069	Intermediate Similarity	NPD1202	Approved
0.7067	Intermediate Similarity	NPD1934	Approved
0.7063	Intermediate Similarity	NPD1195	Approved
0.7055	Intermediate Similarity	NPD4661	Approved
0.7055	Intermediate Similarity	NPD4662	Approved
0.7055	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6355	Discontinued
0.7034	Intermediate Similarity	NPD7440	Discontinued
0.7031	Intermediate Similarity	NPD256	Approved
0.7031	Intermediate Similarity	NPD255	Approved
0.7029	Intermediate Similarity	NPD6233	Phase 2
0.7021	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3748	Approved
0.7021	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2801	Approved
0.7015	Intermediate Similarity	NPD1283	Approved
0.7007	Intermediate Similarity	NPD1512	Approved
0.7007	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5889	Approved
0.7	Intermediate Similarity	NPD2366	Approved
0.7	Intermediate Similarity	NPD5890	Approved
0.7	Intermediate Similarity	NPD6651	Approved
0.6993	Remote Similarity	NPD3749	Approved
0.6993	Remote Similarity	NPD955	Approved
0.6993	Remote Similarity	NPD9277	Approved
0.6993	Remote Similarity	NPD75	Approved
0.6992	Remote Similarity	NPD968	Approved
0.6986	Remote Similarity	NPD1543	Discontinued
0.6985	Remote Similarity	NPD454	Approved
0.698	Remote Similarity	NPD7458	Discontinued
0.698	Remote Similarity	NPD3455	Phase 2
0.6972	Remote Similarity	NPD4476	Approved
0.6972	Remote Similarity	NPD4477	Approved
0.697	Remote Similarity	NPD3847	Discontinued
0.6967	Remote Similarity	NPD5909	Discontinued
0.6957	Remote Similarity	NPD1048	Approved
0.695	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD844	Approved
0.6947	Remote Similarity	NPD5585	Approved
0.6937	Remote Similarity	NPD5953	Discontinued
0.6933	Remote Similarity	NPD3684	Discontinued
0.6929	Remote Similarity	NPD5277	Phase 2
0.6928	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9275	Approved
0.6923	Remote Similarity	NPD6005	Phase 3
0.6923	Remote Similarity	NPD6232	Discontinued
0.6923	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9274	Approved
0.6923	Remote Similarity	NPD6004	Phase 3
0.6923	Remote Similarity	NPD9278	Suspended
0.6923	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6002	Phase 3
0.6923	Remote Similarity	NPD9276	Approved
0.6923	Remote Similarity	NPD845	Approved
0.6918	Remote Similarity	NPD7286	Phase 2
0.6912	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4062	Phase 3
0.6897	Remote Similarity	NPD8166	Discontinued
0.6894	Remote Similarity	NPD17	Approved
0.6892	Remote Similarity	NPD6273	Approved
0.6889	Remote Similarity	NPD1876	Approved
0.6887	Remote Similarity	NPD2672	Discontinued
0.6885	Remote Similarity	NPD6647	Phase 2
0.6884	Remote Similarity	NPD7008	Discontinued
0.687	Remote Similarity	NPD1548	Phase 1
0.6864	Remote Similarity	NPD2934	Approved
0.6864	Remote Similarity	NPD2933	Approved
0.6863	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3140	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