NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	236.1
Volume:	246.826
LogP:	2.259
LogD:	1.971
LogS:	-2.707
# Rotatable Bonds:	5
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.616
Synthetic Accessibility Score:	2.797
Fsp3:	0.308
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:	-4.455
MDCK Permeability:	1.5690946383983828e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.045
30% Bioavailability (F30%):	0.428

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.47
Plasma Protein Binding (PPB):	69.19757843017578%
Volume Distribution (VD):	0.86
Pgp-substrate:	20.331222534179688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.627
CYP1A2-substrate:	0.881
CYP2C19-inhibitor:	0.129
CYP2C19-substrate:	0.243
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.8
CYP2D6-inhibitor:	0.068
CYP2D6-substrate:	0.678
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.26

ADMET: Excretion

Clearance (CL):	13.291
Half-life (T1/2):	0.897

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.09
Drug-inuced Liver Injury (DILI):	0.427
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.462
Skin Sensitization:	0.13
Carcinogencity:	0.039
Eye Corrosion:	0.005
Eye Irritation:	0.785
Respiratory Toxicity:	0.164

Download Data

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

Natural Product: NPC473744

Natural Product ID:	NPC473744
*Common Name:**	Methyl 4-Hydroxy-3-(2-Hydroxy-3-Methylbut-3-Enyl)Benzoate
IUPAC Name:	methyl 4-hydroxy-3-(2-hydroxy-3-methylbut-3-enyl)benzoate
Synonyms:
Standard InCHIKey:	ADJMAKIJBCRROI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H16O4/c1-8(2)12(15)7-10-6-9(13(16)17-3)4-5-11(10)14/h4-6,12,14-15H,1,7H2,2-3H3
SMILES:	CC(=C)C(CC1=C(C=CC(=C1)C(=O)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450751
PubChem CID:	13846908
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:0004701] p-Hydroxybenzoic acid esters [CHEMONTID:0004702] p-Hydroxybenzoic acid alkyl 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
NPO33179	piper sp.	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568762]
NPO16463	Piper glabratum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18712933]
NPO16463	Piper glabratum	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18712933]
NPO16463	Piper glabratum	Species	Piperaceae	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	5
Others	2

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	IC50	=	78.2	ug.mL-1	PMID[460999]
NPT1208	Organism	Leishmania braziliensis	Leishmania braziliensis	IC50	=	74.4	ug.mL-1	PMID[460999]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	86.9	ug.mL-1	PMID[460999]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	15.6	ug.mL-1	PMID[460999]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	10.0	ug.mL-1	PMID[460999]
NPT487	Organism	Cladosporium cladosporioides	Cladosporium cladosporioides	Activity	=	5.0	ug	PMID[461000]
NPT488	Organism	Cladosporium sphaerospermum	Cladosporium sphaerospermum	Activity	=	5.0	ug	PMID[461000]

☑ 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 NPC473744 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	278
0.1-0.2	1205
0.2-0.3	3114
0.3-0.4	7233
0.4-0.5	11221
0.5-0.6	4377
0.6-0.7	8693
0.7-0.8	6063
0.8-0.85	461
0.85-0.9	42
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9758	High Similarity	NPC473777
0.9508	High Similarity	NPC184219
0.9504	High Similarity	NPC67300
0.9344	High Similarity	NPC475192
0.9231	High Similarity	NPC475111
0.9219	High Similarity	NPC302844
0.92	High Similarity	NPC110211
0.9048	High Similarity	NPC204579
0.9016	High Similarity	NPC473767
0.9	High Similarity	NPC239855
0.8976	High Similarity	NPC121104
0.8955	High Similarity	NPC469911
0.8934	High Similarity	NPC94298
0.8934	High Similarity	NPC474890
0.8934	High Similarity	NPC161943
0.8934	High Similarity	NPC273282
0.8934	High Similarity	NPC27633
0.8926	High Similarity	NPC131192
0.8889	High Similarity	NPC184053
0.8819	High Similarity	NPC49938
0.877	High Similarity	NPC83718
0.8676	High Similarity	NPC64664
0.8667	High Similarity	NPC221104
0.8657	High Similarity	NPC291454
0.8657	High Similarity	NPC84699
0.8647	High Similarity	NPC204582
0.8633	High Similarity	NPC97188
0.8626	High Similarity	NPC109778
0.8626	High Similarity	NPC163169
0.8626	High Similarity	NPC123
0.8615	High Similarity	NPC2596
0.8613	High Similarity	NPC470842
0.8605	High Similarity	NPC95309
0.8605	High Similarity	NPC473751
0.8582	High Similarity	NPC142027
0.8582	High Similarity	NPC164136
0.8571	High Similarity	NPC114116
0.856	High Similarity	NPC61779
0.8551	High Similarity	NPC321980
0.8551	High Similarity	NPC470087
0.855	High Similarity	NPC194979
0.855	High Similarity	NPC226855
0.8538	High Similarity	NPC158654
0.8529	High Similarity	NPC112135
0.8529	High Similarity	NPC212693
0.8529	High Similarity	NPC94248
0.8525	High Similarity	NPC242136
0.8516	High Similarity	NPC174991
0.8485	Intermediate Similarity	NPC327457
0.8485	Intermediate Similarity	NPC86774
0.8478	Intermediate Similarity	NPC472604
0.8478	Intermediate Similarity	NPC472605
0.8473	Intermediate Similarity	NPC2401
0.8467	Intermediate Similarity	NPC139634
0.8467	Intermediate Similarity	NPC105456
0.8462	Intermediate Similarity	NPC474944
0.8462	Intermediate Similarity	NPC476022
0.8462	Intermediate Similarity	NPC474945
0.8462	Intermediate Similarity	NPC475236
0.8456	Intermediate Similarity	NPC194579
0.8456	Intermediate Similarity	NPC70380
0.8451	Intermediate Similarity	NPC17600
0.845	Intermediate Similarity	NPC221798
0.8444	Intermediate Similarity	NPC27407
0.844	Intermediate Similarity	NPC469498
0.8438	Intermediate Similarity	NPC291189
0.8438	Intermediate Similarity	NPC69403
0.8433	Intermediate Similarity	NPC40524
0.8433	Intermediate Similarity	NPC139074
0.8433	Intermediate Similarity	NPC213485
0.8429	Intermediate Similarity	NPC245482
0.8429	Intermediate Similarity	NPC476178
0.8429	Intermediate Similarity	NPC51887
0.8429	Intermediate Similarity	NPC117836
0.8429	Intermediate Similarity	NPC42540
0.8429	Intermediate Similarity	NPC151607
0.8429	Intermediate Similarity	NPC301751
0.8429	Intermediate Similarity	NPC475705
0.8417	Intermediate Similarity	NPC470089
0.8409	Intermediate Similarity	NPC66246
0.8409	Intermediate Similarity	NPC170546
0.8409	Intermediate Similarity	NPC939
0.8406	Intermediate Similarity	NPC158472
0.8406	Intermediate Similarity	NPC472601
0.8406	Intermediate Similarity	NPC470211
0.8406	Intermediate Similarity	NPC472600
0.8403	Intermediate Similarity	NPC11892
0.8394	Intermediate Similarity	NPC478200
0.8394	Intermediate Similarity	NPC191835
0.8394	Intermediate Similarity	NPC33144
0.8392	Intermediate Similarity	NPC52931
0.8392	Intermediate Similarity	NPC247219
0.8382	Intermediate Similarity	NPC158481
0.838	Intermediate Similarity	NPC66991
0.837	Intermediate Similarity	NPC27643
0.8369	Intermediate Similarity	NPC257558
0.8369	Intermediate Similarity	NPC83272
0.8357	Intermediate Similarity	NPC471731
0.8357	Intermediate Similarity	NPC51106
0.8357	Intermediate Similarity	NPC148545
0.8357	Intermediate Similarity	NPC159721
0.8347	Intermediate Similarity	NPC471954
0.8347	Intermediate Similarity	NPC75272
0.8346	Intermediate Similarity	NPC183348
0.8346	Intermediate Similarity	NPC42292
0.8346	Intermediate Similarity	NPC307732
0.8346	Intermediate Similarity	NPC282230
0.8346	Intermediate Similarity	NPC245395
0.8345	Intermediate Similarity	NPC478217
0.8345	Intermediate Similarity	NPC472035
0.8345	Intermediate Similarity	NPC472603
0.8345	Intermediate Similarity	NPC478201
0.8345	Intermediate Similarity	NPC158634
0.8345	Intermediate Similarity	NPC313123
0.8345	Intermediate Similarity	NPC244923
0.8333	Intermediate Similarity	NPC19622
0.8333	Intermediate Similarity	NPC229894
0.8333	Intermediate Similarity	NPC112789
0.8333	Intermediate Similarity	NPC37642
0.8333	Intermediate Similarity	NPC476024
0.8333	Intermediate Similarity	NPC88269
0.8333	Intermediate Similarity	NPC473988
0.8333	Intermediate Similarity	NPC32360
0.8333	Intermediate Similarity	NPC275356
0.8321	Intermediate Similarity	NPC24394
0.8321	Intermediate Similarity	NPC301915
0.8321	Intermediate Similarity	NPC477592
0.8321	Intermediate Similarity	NPC261292
0.8321	Intermediate Similarity	NPC170718
0.8321	Intermediate Similarity	NPC71256
0.831	Intermediate Similarity	NPC473023
0.831	Intermediate Similarity	NPC286038
0.831	Intermediate Similarity	NPC316769
0.8309	Intermediate Similarity	NPC283590
0.8309	Intermediate Similarity	NPC61153
0.8309	Intermediate Similarity	NPC70859
0.8309	Intermediate Similarity	NPC130899
0.8308	Intermediate Similarity	NPC474803
0.8306	Intermediate Similarity	NPC81808
0.8298	Intermediate Similarity	NPC478203
0.8298	Intermediate Similarity	NPC213900
0.8298	Intermediate Similarity	NPC126882
0.8298	Intermediate Similarity	NPC469683
0.8298	Intermediate Similarity	NPC210966
0.8296	Intermediate Similarity	NPC66158
0.8296	Intermediate Similarity	NPC153783
0.8286	Intermediate Similarity	NPC469404
0.8286	Intermediate Similarity	NPC471733
0.8286	Intermediate Similarity	NPC474385
0.8284	Intermediate Similarity	NPC196979
0.8284	Intermediate Similarity	NPC214702
0.8284	Intermediate Similarity	NPC15083
0.8284	Intermediate Similarity	NPC219892
0.8284	Intermediate Similarity	NPC475042
0.8284	Intermediate Similarity	NPC189823
0.8284	Intermediate Similarity	NPC470976
0.8284	Intermediate Similarity	NPC470977
0.8284	Intermediate Similarity	NPC470831
0.8276	Intermediate Similarity	NPC475093
0.8273	Intermediate Similarity	NPC37206
0.8273	Intermediate Similarity	NPC99441
0.8273	Intermediate Similarity	NPC137009
0.8273	Intermediate Similarity	NPC327187
0.8273	Intermediate Similarity	NPC275903
0.8273	Intermediate Similarity	NPC168471
0.8271	Intermediate Similarity	NPC117899
0.8268	Intermediate Similarity	NPC90522
0.8268	Intermediate Similarity	NPC328459
0.8264	Intermediate Similarity	NPC179128
0.8264	Intermediate Similarity	NPC267469
0.8264	Intermediate Similarity	NPC87630
0.8264	Intermediate Similarity	NPC116292
0.8261	Intermediate Similarity	NPC197666
0.8261	Intermediate Similarity	NPC126739
0.8261	Intermediate Similarity	NPC23870
0.8261	Intermediate Similarity	NPC472602
0.8258	Intermediate Similarity	NPC37512
0.8254	Intermediate Similarity	NPC174087
0.8252	Intermediate Similarity	NPC472036
0.8252	Intermediate Similarity	NPC477483
0.8252	Intermediate Similarity	NPC53362
0.8252	Intermediate Similarity	NPC166583
0.8252	Intermediate Similarity	NPC325032
0.8252	Intermediate Similarity	NPC222298
0.8252	Intermediate Similarity	NPC51070
0.8252	Intermediate Similarity	NPC81835
0.8248	Intermediate Similarity	NPC156892
0.8248	Intermediate Similarity	NPC235115
0.8248	Intermediate Similarity	NPC326847
0.8244	Intermediate Similarity	NPC472592
0.8244	Intermediate Similarity	NPC165556
0.824	Intermediate Similarity	NPC220540
0.8239	Intermediate Similarity	NPC208293
0.8239	Intermediate Similarity	NPC258856
0.8239	Intermediate Similarity	NPC75295
0.8235	Intermediate Similarity	NPC474097
0.8227	Intermediate Similarity	NPC469542
0.8227	Intermediate Similarity	NPC294432
0.8227	Intermediate Similarity	NPC478202
0.8227	Intermediate Similarity	NPC271451

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 NPC473744 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	838
0.2-0.3	1564
0.3-0.4	2490
0.4-0.5	2091
0.5-0.6	1232
0.6-0.7	534
0.7-0.8	150
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8934	High Similarity	NPD9545	Approved
0.8406	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD4628	Phase 3
0.8188	Intermediate Similarity	NPD2935	Discontinued
0.8182	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD9493	Approved
0.8162	Intermediate Similarity	NPD230	Phase 1
0.7986	Intermediate Similarity	NPD1510	Phase 2
0.7959	Intermediate Similarity	NPD4380	Phase 2
0.7956	Intermediate Similarity	NPD1240	Approved
0.7941	Intermediate Similarity	NPD3764	Approved
0.7881	Intermediate Similarity	NPD7075	Discontinued
0.7862	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2532	Approved
0.7862	Intermediate Similarity	NPD2534	Approved
0.7862	Intermediate Similarity	NPD2533	Approved
0.7846	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1607	Approved
0.7817	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD1549	Phase 2
0.78	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD7411	Suspended
0.7746	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6801	Discontinued
0.773	Intermediate Similarity	NPD2799	Discontinued
0.7708	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD1164	Approved
0.7682	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD7819	Suspended
0.7681	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7458	Discontinued
0.7622	Intermediate Similarity	NPD6002	Phase 3
0.7622	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6005	Phase 3
0.7622	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6004	Phase 3
0.7612	Intermediate Similarity	NPD9717	Approved
0.7586	Intermediate Similarity	NPD7003	Approved
0.7586	Intermediate Similarity	NPD3750	Approved
0.7582	Intermediate Similarity	NPD7768	Phase 2
0.7582	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD2313	Discontinued
0.7552	Intermediate Similarity	NPD2796	Approved
0.7552	Intermediate Similarity	NPD1551	Phase 2
0.7551	Intermediate Similarity	NPD6799	Approved
0.7547	Intermediate Similarity	NPD5844	Phase 1
0.754	Intermediate Similarity	NPD9266	Approved
0.754	Intermediate Similarity	NPD74	Approved
0.7534	Intermediate Similarity	NPD6190	Approved
0.7532	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD4626	Approved
0.7518	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD920	Approved
0.7516	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7033	Discontinued
0.7481	Intermediate Similarity	NPD9269	Phase 2
0.7481	Intermediate Similarity	NPD1608	Approved
0.7468	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD9494	Approved
0.746	Intermediate Similarity	NPD9263	Approved
0.746	Intermediate Similarity	NPD9267	Approved
0.746	Intermediate Similarity	NPD9264	Approved
0.7452	Intermediate Similarity	NPD6232	Discontinued
0.7445	Intermediate Similarity	NPD1203	Approved
0.7444	Intermediate Similarity	NPD9268	Approved
0.7431	Intermediate Similarity	NPD5406	Approved
0.7431	Intermediate Similarity	NPD5405	Approved
0.7431	Intermediate Similarity	NPD5408	Approved
0.7431	Intermediate Similarity	NPD5404	Approved
0.7417	Intermediate Similarity	NPD3226	Approved
0.7397	Intermediate Similarity	NPD1243	Approved
0.7388	Intermediate Similarity	NPD1778	Approved
0.7386	Intermediate Similarity	NPD1934	Approved
0.7383	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1283	Approved
0.7368	Intermediate Similarity	NPD6599	Discontinued
0.7365	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3972	Approved
0.7343	Intermediate Similarity	NPD6651	Approved
0.7329	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD943	Approved
0.7319	Intermediate Similarity	NPD1470	Approved
0.7315	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD5691	Approved
0.7312	Intermediate Similarity	NPD7473	Discontinued
0.7305	Intermediate Similarity	NPD6798	Discontinued
0.7303	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD6832	Phase 2
0.7279	Intermediate Similarity	NPD1201	Approved
0.7279	Intermediate Similarity	NPD422	Phase 1
0.7279	Intermediate Similarity	NPD2800	Approved
0.7273	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD6355	Discontinued
0.7273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD447	Suspended
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD2798	Approved
0.7266	Intermediate Similarity	NPD2182	Approved
0.7266	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1019	Discontinued
0.726	Intermediate Similarity	NPD2344	Approved
0.726	Intermediate Similarity	NPD2346	Discontinued
0.7259	Intermediate Similarity	NPD17	Approved
0.7252	Intermediate Similarity	NPD1241	Discontinued
0.7241	Intermediate Similarity	NPD4308	Phase 3
0.7241	Intermediate Similarity	NPD3748	Approved
0.7239	Intermediate Similarity	NPD5953	Discontinued
0.723	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD3400	Discontinued
0.7226	Intermediate Similarity	NPD1481	Phase 2
0.7222	Intermediate Similarity	NPD7286	Phase 2
0.7222	Intermediate Similarity	NPD164	Approved
0.7219	Intermediate Similarity	NPD6273	Approved
0.7206	Intermediate Similarity	NPD3496	Discontinued
0.72	Intermediate Similarity	NPD1511	Approved
0.7197	Intermediate Similarity	NPD9281	Approved
0.7195	Intermediate Similarity	NPD6559	Discontinued
0.7194	Intermediate Similarity	NPD2797	Approved
0.7192	Intermediate Similarity	NPD4477	Approved
0.7192	Intermediate Similarity	NPD4476	Approved
0.7188	Intermediate Similarity	NPD1358	Approved
0.7183	Intermediate Similarity	NPD411	Approved
0.7183	Intermediate Similarity	NPD3268	Approved
0.7179	Intermediate Similarity	NPD3817	Phase 2
0.7171	Intermediate Similarity	NPD5403	Approved
0.717	Intermediate Similarity	NPD6959	Discontinued
0.716	Intermediate Similarity	NPD3818	Discontinued
0.7153	Intermediate Similarity	NPD1535	Discovery
0.7153	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1281	Approved
0.7143	Intermediate Similarity	NPD9261	Approved
0.7143	Intermediate Similarity	NPD6166	Phase 2
0.7143	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7266	Discontinued
0.7143	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3882	Suspended
0.7134	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5710	Approved
0.7125	Intermediate Similarity	NPD5711	Approved
0.7123	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD8455	Phase 2
0.7115	Intermediate Similarity	NPD2801	Approved
0.7114	Intermediate Similarity	NPD8166	Discontinued
0.7113	Intermediate Similarity	NPD7008	Discontinued
0.7113	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD3134	Approved
0.7105	Intermediate Similarity	NPD9509	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1512	Approved
0.7097	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3749	Approved
0.7087	Intermediate Similarity	NPD1237	Approved
0.7086	Intermediate Similarity	NPD7390	Discontinued
0.7083	Intermediate Similarity	NPD8150	Discontinued
0.7083	Intermediate Similarity	NPD4060	Phase 1
0.7083	Intermediate Similarity	NPD2979	Phase 3
0.708	Intermediate Similarity	NPD3847	Discontinued
0.7078	Intermediate Similarity	NPD3455	Phase 2
0.7073	Intermediate Similarity	NPD7074	Phase 3
0.707	Intermediate Similarity	NPD5402	Approved
0.7067	Intermediate Similarity	NPD2309	Approved
0.7067	Intermediate Similarity	NPD3887	Approved
0.7063	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD940	Approved
0.7063	Intermediate Similarity	NPD846	Approved
0.7059	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7177	Discontinued
0.7044	Intermediate Similarity	NPD919	Approved
0.704	Intermediate Similarity	NPD1238	Approved
0.7039	Intermediate Similarity	NPD5401	Approved
0.7034	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD5048	Discontinued
0.702	Intermediate Similarity	NPD7236	Approved
0.702	Intermediate Similarity	NPD7440	Discontinued
0.7018	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD256	Approved
0.7015	Intermediate Similarity	NPD255	Approved
0.7014	Intermediate Similarity	NPD520	Approved
0.7014	Intermediate Similarity	NPD6233	Phase 2
0.7014	Intermediate Similarity	NPD6663	Approved
0.7012	Intermediate Similarity	NPD7054	Approved
0.7006	Intermediate Similarity	NPD1465	Phase 2
0.7	Intermediate Similarity	NPD3225	Approved
0.7	Intermediate Similarity	NPD1876	Approved
0.7	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5494	Approved
0.6993	Remote Similarity	NPD5049	Phase 3
0.6987	Remote Similarity	NPD6385	Approved
0.6987	Remote Similarity	NPD6386	Approved
0.6985	Remote Similarity	NPD1894	Discontinued
0.698	Remote Similarity	NPD2424	Discontinued
0.6972	Remote Similarity	NPD5736	Approved
0.697	Remote Similarity	NPD7472	Approved
0.6966	Remote Similarity	NPD4307	Phase 2
0.696	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