NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	252.1
Volume:	255.617
LogP:	2.027
LogD:	0.957
LogS:	-2.034
# Rotatable Bonds:	5
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.628
Synthetic Accessibility Score:	2.373
Fsp3:	0.385
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.615
MDCK Permeability:	1.5922949387459084e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.055
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.065
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	89.7054672241211%
Volume Distribution (VD):	0.409
Pgp-substrate:	5.626461029052734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.638
CYP1A2-substrate:	0.828
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.203
CYP2C9-inhibitor:	0.303
CYP2C9-substrate:	0.686
CYP2D6-inhibitor:	0.087
CYP2D6-substrate:	0.296
CYP3A4-inhibitor:	0.078
CYP3A4-substrate:	0.275

ADMET: Excretion

Clearance (CL):	15.439
Half-life (T1/2):	0.948

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.08
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.72
Carcinogencity:	0.02
Eye Corrosion:	0.014
Eye Irritation:	0.627
Respiratory Toxicity:	0.133

Download Data

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

Natural Product: NPC475111

Natural Product ID:	NPC475111
*Common Name:**	Methyl 3,4-Dihydroxy-5-(2-Hydroxy-3-Methylbut-3-Enyl)Benzoate
IUPAC Name:	methyl 3,4-dihydroxy-5-(2-hydroxy-3-methylbut-3-enyl)benzoate
Synonyms:
Standard InCHIKey:	KVDSAANFJMQAKH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H16O5/c1-7(2)10(14)5-8-4-9(13(17)18-3)6-11(15)12(8)16/h4,6,10,14-16H,1,5H2,2-3H3
SMILES:	CC(=C)C(CC1=C(C(=CC(=C1)C(=O)OC)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498337
PubChem CID:	25058113
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
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

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	IC50	=	89.5	ug.mL-1	PMID[505597]
NPT1208	Organism	Leishmania braziliensis	Leishmania braziliensis	IC50	=	81.9	ug.mL-1	PMID[505597]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	81.9	ug.mL-1	PMID[505597]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	16.4	ug.mL-1	PMID[505597]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	10.0	ug.mL-1	PMID[505597]

☑ 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 NPC475111 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	303
0.1-0.2	1322
0.2-0.3	3536
0.3-0.4	7766
0.4-0.5	10694
0.5-0.6	4016
0.6-0.7	7528
0.7-0.8	7023
0.8-0.85	454
0.85-0.9	45
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC239855
0.9394	High Similarity	NPC204582
0.9313	High Similarity	NPC473777
0.9259	High Similarity	NPC112135
0.9231	High Similarity	NPC473744
0.916	High Similarity	NPC226855
0.9154	High Similarity	NPC158654
0.8986	High Similarity	NPC327187
0.8971	High Similarity	NPC156892
0.8971	High Similarity	NPC326847
0.8936	High Similarity	NPC75295
0.8936	High Similarity	NPC258856
0.8897	High Similarity	NPC18646
0.8889	High Similarity	NPC1321
0.8889	High Similarity	NPC304929
0.8889	High Similarity	NPC156124
0.8881	High Similarity	NPC264145
0.8865	High Similarity	NPC213900
0.8865	High Similarity	NPC469683
0.8815	High Similarity	NPC302844
0.8794	High Similarity	NPC469615
0.8779	High Similarity	NPC184219
0.8777	High Similarity	NPC75763
0.8777	High Similarity	NPC225036
0.8777	High Similarity	NPC12218
0.8777	High Similarity	NPC105525
0.8769	High Similarity	NPC475192
0.8769	High Similarity	NPC67300
0.875	High Similarity	NPC159418
0.875	High Similarity	NPC283823
0.8732	High Similarity	NPC113397
0.8731	High Similarity	NPC94810
0.8707	High Similarity	NPC62051
0.8705	High Similarity	NPC239943
0.8676	High Similarity	NPC111888
0.8662	High Similarity	NPC50954
0.8647	High Similarity	NPC476022
0.8647	High Similarity	NPC474945
0.8643	High Similarity	NPC471819
0.8611	High Similarity	NPC268366
0.8601	High Similarity	NPC275278
0.8582	High Similarity	NPC469911
0.8571	High Similarity	NPC124842
0.8562	High Similarity	NPC142654
0.8561	High Similarity	NPC156307
0.8552	High Similarity	NPC472969
0.8531	High Similarity	NPC229036
0.8531	High Similarity	NPC22176
0.8531	High Similarity	NPC190587
0.8531	High Similarity	NPC121573
0.8531	High Similarity	NPC473090
0.8531	High Similarity	NPC226738
0.8531	High Similarity	NPC50221
0.8531	High Similarity	NPC114242
0.8529	High Similarity	NPC123
0.8529	High Similarity	NPC163169
0.8529	High Similarity	NPC285776
0.8521	High Similarity	NPC184053
0.8507	High Similarity	NPC110211
0.85	High Similarity	NPC110899
0.85	High Similarity	NPC25305
0.85	High Similarity	NPC112068
0.85	High Similarity	NPC125417
0.85	High Similarity	NPC95679
0.8493	Intermediate Similarity	NPC476394
0.8493	Intermediate Similarity	NPC98809
0.8489	Intermediate Similarity	NPC29317
0.8489	Intermediate Similarity	NPC176102
0.8489	Intermediate Similarity	NPC229638
0.8489	Intermediate Similarity	NPC254832
0.8489	Intermediate Similarity	NPC71108
0.8489	Intermediate Similarity	NPC139519
0.8489	Intermediate Similarity	NPC267539
0.8489	Intermediate Similarity	NPC204257
0.8483	Intermediate Similarity	NPC229264
0.8483	Intermediate Similarity	NPC474991
0.8478	Intermediate Similarity	NPC200422
0.8478	Intermediate Similarity	NPC295406
0.8478	Intermediate Similarity	NPC289572
0.8478	Intermediate Similarity	NPC307006
0.8478	Intermediate Similarity	NPC129889
0.8478	Intermediate Similarity	NPC157478
0.8472	Intermediate Similarity	NPC105213
0.8472	Intermediate Similarity	NPC108455
0.8467	Intermediate Similarity	NPC318799
0.8462	Intermediate Similarity	NPC314271
0.8462	Intermediate Similarity	NPC156654
0.8456	Intermediate Similarity	NPC116850
0.8456	Intermediate Similarity	NPC197188
0.8456	Intermediate Similarity	NPC291510
0.8456	Intermediate Similarity	NPC43872
0.8456	Intermediate Similarity	NPC238672
0.8456	Intermediate Similarity	NPC281477
0.8456	Intermediate Similarity	NPC144801
0.8451	Intermediate Similarity	NPC64664
0.8446	Intermediate Similarity	NPC227485
0.8446	Intermediate Similarity	NPC221249
0.844	Intermediate Similarity	NPC325625
0.8425	Intermediate Similarity	NPC127046
0.8425	Intermediate Similarity	NPC166583
0.8425	Intermediate Similarity	NPC53362
0.8417	Intermediate Similarity	NPC106406
0.8414	Intermediate Similarity	NPC83272
0.8414	Intermediate Similarity	NPC473867
0.8414	Intermediate Similarity	NPC84786
0.84	Intermediate Similarity	NPC180901
0.84	Intermediate Similarity	NPC82592
0.84	Intermediate Similarity	NPC300757
0.84	Intermediate Similarity	NPC16082
0.8392	Intermediate Similarity	NPC477277
0.8392	Intermediate Similarity	NPC477278
0.8389	Intermediate Similarity	NPC131121
0.8389	Intermediate Similarity	NPC323626
0.8389	Intermediate Similarity	NPC324233
0.838	Intermediate Similarity	NPC205751
0.838	Intermediate Similarity	NPC476819
0.838	Intermediate Similarity	NPC274891
0.838	Intermediate Similarity	NPC474875
0.838	Intermediate Similarity	NPC476820
0.838	Intermediate Similarity	NPC303683
0.838	Intermediate Similarity	NPC26241
0.838	Intermediate Similarity	NPC295492
0.837	Intermediate Similarity	NPC474944
0.837	Intermediate Similarity	NPC204579
0.8358	Intermediate Similarity	NPC469568
0.8356	Intermediate Similarity	NPC473023
0.8356	Intermediate Similarity	NPC191899
0.8356	Intermediate Similarity	NPC246229
0.8333	Intermediate Similarity	NPC281703
0.8333	Intermediate Similarity	NPC125487
0.8323	Intermediate Similarity	NPC471788
0.8322	Intermediate Similarity	NPC471853
0.8322	Intermediate Similarity	NPC326065
0.8322	Intermediate Similarity	NPC75695
0.8322	Intermediate Similarity	NPC477279
0.8322	Intermediate Similarity	NPC158472
0.8322	Intermediate Similarity	NPC187690
0.8321	Intermediate Similarity	NPC473767
0.8311	Intermediate Similarity	NPC306343
0.831	Intermediate Similarity	NPC37250
0.831	Intermediate Similarity	NPC278068
0.831	Intermediate Similarity	NPC152942
0.831	Intermediate Similarity	NPC126739
0.831	Intermediate Similarity	NPC197666
0.831	Intermediate Similarity	NPC219428
0.831	Intermediate Similarity	NPC221104
0.831	Intermediate Similarity	NPC302857
0.831	Intermediate Similarity	NPC212693
0.831	Intermediate Similarity	NPC142703
0.831	Intermediate Similarity	NPC94248
0.8309	Intermediate Similarity	NPC121104
0.8309	Intermediate Similarity	NPC281020
0.8301	Intermediate Similarity	NPC24627
0.8299	Intermediate Similarity	NPC142528
0.8299	Intermediate Similarity	NPC43123
0.8299	Intermediate Similarity	NPC120621
0.8299	Intermediate Similarity	NPC476463
0.8299	Intermediate Similarity	NPC248257
0.8299	Intermediate Similarity	NPC81835
0.8298	Intermediate Similarity	NPC291454
0.8289	Intermediate Similarity	NPC84935
0.8289	Intermediate Similarity	NPC77679
0.8289	Intermediate Similarity	NPC190020
0.8288	Intermediate Similarity	NPC287495
0.8288	Intermediate Similarity	NPC157133
0.8288	Intermediate Similarity	NPC9370
0.8286	Intermediate Similarity	NPC155098
0.8286	Intermediate Similarity	NPC474895
0.8278	Intermediate Similarity	NPC79998
0.8278	Intermediate Similarity	NPC199926
0.8278	Intermediate Similarity	NPC472835
0.8276	Intermediate Similarity	NPC239608
0.8276	Intermediate Similarity	NPC46161
0.8273	Intermediate Similarity	NPC50763
0.8271	Intermediate Similarity	NPC322332
0.8269	Intermediate Similarity	NPC207575
0.8269	Intermediate Similarity	NPC13481
0.8267	Intermediate Similarity	NPC180388
0.8264	Intermediate Similarity	NPC470842
0.8264	Intermediate Similarity	NPC472605
0.8264	Intermediate Similarity	NPC472604
0.8255	Intermediate Similarity	NPC243891
0.8255	Intermediate Similarity	NPC56204
0.8255	Intermediate Similarity	NPC140151
0.8255	Intermediate Similarity	NPC96501
0.8255	Intermediate Similarity	NPC179178
0.8252	Intermediate Similarity	NPC4796
0.8252	Intermediate Similarity	NPC275356
0.8252	Intermediate Similarity	NPC139634
0.8252	Intermediate Similarity	NPC105456
0.8248	Intermediate Similarity	NPC476024
0.8247	Intermediate Similarity	NPC266365
0.8247	Intermediate Similarity	NPC469889
0.8247	Intermediate Similarity	NPC349525
0.8247	Intermediate Similarity	NPC103201
0.8247	Intermediate Similarity	NPC473106
0.8244	Intermediate Similarity	NPC161943
0.8244	Intermediate Similarity	NPC27633
0.8244	Intermediate Similarity	NPC273282
0.8244	Intermediate Similarity	NPC94298

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 NPC475111 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	901
0.2-0.3	1793
0.3-0.4	2630
0.4-0.5	1891
0.5-0.6	1077
0.6-0.7	486
0.7-0.8	105
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD230	Phase 1
0.8244	Intermediate Similarity	NPD9545	Approved
0.8224	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD9269	Phase 2
0.8092	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD6190	Approved
0.8043	Intermediate Similarity	NPD9494	Approved
0.791	Intermediate Similarity	NPD9268	Approved
0.7891	Intermediate Similarity	NPD4628	Phase 3
0.7887	Intermediate Similarity	NPD943	Approved
0.7862	Intermediate Similarity	NPD2935	Discontinued
0.7823	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD2532	Approved
0.78	Intermediate Similarity	NPD2534	Approved
0.78	Intermediate Similarity	NPD2533	Approved
0.7792	Intermediate Similarity	NPD1934	Approved
0.7736	Intermediate Similarity	NPD6232	Discontinued
0.773	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD5844	Phase 1
0.7671	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4380	Phase 2
0.7654	Intermediate Similarity	NPD3818	Discontinued
0.7643	Intermediate Similarity	NPD3882	Suspended
0.7635	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1465	Phase 2
0.7628	Intermediate Similarity	NPD2801	Approved
0.7616	Intermediate Similarity	NPD1511	Approved
0.7595	Intermediate Similarity	NPD7075	Discontinued
0.7593	Intermediate Similarity	NPD7473	Discontinued
0.7586	Intermediate Similarity	NPD447	Suspended
0.7568	Intermediate Similarity	NPD7266	Discontinued
0.7566	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD9493	Approved
0.7538	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD8166	Discontinued
0.7531	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6166	Phase 2
0.7531	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1512	Approved
0.7516	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3455	Phase 2
0.7471	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3817	Phase 2
0.7455	Intermediate Similarity	NPD7074	Phase 3
0.7452	Intermediate Similarity	NPD6801	Discontinued
0.7432	Intermediate Similarity	NPD1510	Phase 2
0.7425	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7819	Suspended
0.7397	Intermediate Similarity	NPD1240	Approved
0.7394	Intermediate Similarity	NPD7054	Approved
0.7391	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7685	Pre-registration
0.7349	Intermediate Similarity	NPD7472	Approved
0.7342	Intermediate Similarity	NPD37	Approved
0.7338	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6234	Discontinued
0.7315	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2799	Discontinued
0.731	Intermediate Similarity	NPD3027	Phase 3
0.7305	Intermediate Similarity	NPD6797	Phase 2
0.7303	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1607	Approved
0.7294	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1549	Phase 2
0.7284	Intermediate Similarity	NPD5494	Approved
0.7279	Intermediate Similarity	NPD825	Approved
0.7279	Intermediate Similarity	NPD826	Approved
0.7278	Intermediate Similarity	NPD7411	Suspended
0.7278	Intermediate Similarity	NPD6386	Approved
0.7278	Intermediate Similarity	NPD6385	Approved
0.7273	Intermediate Similarity	NPD6799	Approved
0.7267	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7251	Discontinued
0.7261	Intermediate Similarity	NPD3226	Approved
0.7261	Intermediate Similarity	NPD7458	Discontinued
0.7254	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD8150	Discontinued
0.7244	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD919	Approved
0.7219	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD4626	Approved
0.7205	Intermediate Similarity	NPD4965	Approved
0.7205	Intermediate Similarity	NPD4967	Phase 2
0.7205	Intermediate Similarity	NPD4966	Approved
0.7197	Intermediate Similarity	NPD1653	Approved
0.7183	Intermediate Similarity	NPD1608	Approved
0.7162	Intermediate Similarity	NPD1613	Approved
0.7162	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6559	Discontinued
0.7153	Intermediate Similarity	NPD1164	Approved
0.7153	Intermediate Similarity	NPD1470	Approved
0.7152	Intermediate Similarity	NPD9570	Approved
0.7152	Intermediate Similarity	NPD5404	Approved
0.7152	Intermediate Similarity	NPD5406	Approved
0.7152	Intermediate Similarity	NPD5405	Approved
0.7152	Intermediate Similarity	NPD5408	Approved
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD5402	Approved
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD920	Approved
0.7126	Intermediate Similarity	NPD7228	Approved
0.7118	Intermediate Similarity	NPD7808	Phase 3
0.7107	Intermediate Similarity	NPD6599	Discontinued
0.7105	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6005	Phase 3
0.7105	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6004	Phase 3
0.7105	Intermediate Similarity	NPD2346	Discontinued
0.7105	Intermediate Similarity	NPD6002	Phase 3
0.7103	Intermediate Similarity	NPD258	Approved
0.7103	Intermediate Similarity	NPD257	Approved
0.7099	Intermediate Similarity	NPD7768	Phase 2
0.7092	Intermediate Similarity	NPD1778	Approved
0.7091	Intermediate Similarity	NPD5711	Approved
0.7091	Intermediate Similarity	NPD5710	Approved
0.7086	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1283	Approved
0.7078	Intermediate Similarity	NPD7003	Approved
0.7078	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3750	Approved
0.7063	Intermediate Similarity	NPD9717	Approved
0.7059	Intermediate Similarity	NPD228	Approved
0.7047	Intermediate Similarity	NPD4060	Phase 1
0.7044	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1551	Phase 2
0.7039	Intermediate Similarity	NPD2796	Approved
0.7037	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD8127	Discontinued
0.703	Intermediate Similarity	NPD6959	Discontinued
0.703	Intermediate Similarity	NPD1247	Approved
0.7027	Intermediate Similarity	NPD6798	Discontinued
0.7021	Intermediate Similarity	NPD5691	Approved
0.7013	Intermediate Similarity	NPD1243	Approved
0.7013	Intermediate Similarity	NPD2800	Approved
0.7006	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD555	Phase 2
0.7	Intermediate Similarity	NPD6355	Discontinued
0.6993	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1201	Approved
0.6986	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.698	Remote Similarity	NPD259	Phase 1
0.6977	Remote Similarity	NPD8313	Approved
0.6977	Remote Similarity	NPD8312	Approved
0.6974	Remote Similarity	NPD7033	Discontinued
0.6972	Remote Similarity	NPD17	Approved
0.6963	Remote Similarity	NPD74	Approved
0.6963	Remote Similarity	NPD9266	Approved
0.6962	Remote Similarity	NPD6273	Approved
0.6954	Remote Similarity	NPD6651	Approved
0.6946	Remote Similarity	NPD5242	Approved
0.6943	Remote Similarity	NPD7390	Discontinued
0.6939	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD824	Approved
0.6929	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7199	Phase 2
0.6923	Remote Similarity	NPD3496	Discontinued
0.6918	Remote Similarity	NPD5403	Approved
0.6918	Remote Similarity	NPD1203	Approved
0.6913	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD411	Approved
0.6912	Remote Similarity	NPD3022	Approved
0.6912	Remote Similarity	NPD3021	Approved
0.6901	Remote Similarity	NPD5953	Discontinued
0.6892	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD9263	Approved
0.6889	Remote Similarity	NPD9267	Approved
0.6889	Remote Similarity	NPD9264	Approved
0.6883	Remote Similarity	NPD2344	Approved
0.6882	Remote Similarity	NPD7286	Phase 2
0.6879	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1281	Approved
0.6871	Remote Similarity	NPD8455	Phase 2
0.6861	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7039	Approved
0.686	Remote Similarity	NPD7038	Approved
0.6859	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4110	Phase 3
0.6857	Remote Similarity	NPD8434	Phase 2
0.6839	Remote Similarity	NPD2424	Discontinued
0.6838	Remote Similarity	NPD2182	Approved
0.6828	Remote Similarity	NPD3972	Approved
0.6824	Remote Similarity	NPD7177	Discontinued
0.6824	Remote Similarity	NPD9569	Approved
0.6821	Remote Similarity	NPD2979	Phase 3
0.6792	Remote Similarity	NPD5401	Approved
0.6792	Remote Similarity	NPD3146	Approved
0.6792	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD164	Approved
0.6786	Remote Similarity	NPD2629	Approved
0.6779	Remote Similarity	NPD6832	Phase 2
0.6776	Remote Similarity	NPD274	Approved
0.6776	Remote Similarity	NPD275	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