NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	120.09
Volume:	147.754
LogP:	3.587
LogD:	3.578
LogS:	-3.465
# Rotatable Bonds:	0
TPSA:	0.0
# H-Bond Aceptor:	0
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	0

MedChem Properties

QED Drug-Likeness Score:	0.493
Synthetic Accessibility Score:	1.323
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.332
MDCK Permeability:	2.3388396584778093e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.276
30% Bioavailability (F30%):	0.851

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.984
Plasma Protein Binding (PPB):	89.20020294189453%
Volume Distribution (VD):	0.766
Pgp-substrate:	6.585850715637207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.763
CYP1A2-substrate:	0.922
CYP2C19-inhibitor:	0.758
CYP2C19-substrate:	0.896
CYP2C9-inhibitor:	0.143
CYP2C9-substrate:	0.485
CYP2D6-inhibitor:	0.387
CYP2D6-substrate:	0.881
CYP3A4-inhibitor:	0.145
CYP3A4-substrate:	0.534

ADMET: Excretion

Clearance (CL):	10.798
Half-life (T1/2):	0.758

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.172
Drug-inuced Liver Injury (DILI):	0.055
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.098
Skin Sensitization:	0.344
Carcinogencity:	0.247
Eye Corrosion:	0.973
Eye Irritation:	0.994
Respiratory Toxicity:	0.091

Download Data

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

Natural Product: NPC64270

Natural Product ID:	NPC64270
*Common Name:**	1,3,5-Trimethylbenzene
IUPAC Name:	1,3,5-trimethylbenzene
Synonyms:	1,3,5-Trimethylbenzene
Standard InCHIKey:	AUHZEENZYGFFBQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H12/c1-7-4-8(2)6-9(3)5-7/h4-6H,1-3H3
SMILES:	Cc1cc(C)cc(c1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1797281
PubChem CID:	7947
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives

*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
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/hlca.19270100148]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	2007; 2008	DOI[10.1007/s11746-010-1589-7]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	cotyledon	n.a.	PMID[11283027]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	seed	n.a.	PMID[12670184]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14600382]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	Petals	n.a.	n.a.	PMID[15043425]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	seed	n.a.	PMID[21348467]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22537213]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24338885]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[25894905]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Peanut Skins	n.a.	n.a.	PMID[28231711]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28358502]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.		Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.		n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Leaf	n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Oil	n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Seed	n.a.	n.a.	Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	Silk Stigma Style	n.a.	n.a.	Database[FooDB]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Oils	n.a.		Database[Phenol-Explorer]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Seeds	n.a.		Database[Phenol-Explorer]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	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
Others	1
Potency	6

Activity Type	# Activity
Others	7

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.	LogP	=	4.089	n.a.	PMID[464888]
NPT2	Others	Unspecified	Potency	n.a.	24223.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	Potency	n.a.	21589	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	Potency	n.a.	26945.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	Potency	n.a.	2158.9	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 NPC64270 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	1228
0.1-0.2	4947
0.2-0.3	16307
0.3-0.4	15218
0.4-0.5	3837
0.5-0.6	824
0.6-0.7	218
0.7-0.8	63
0.8-0.85	25
0.85-0.9	19
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9821	High Similarity	NPC147062
0.9649	High Similarity	NPC150196
0.9322	High Similarity	NPC45756
0.9286	High Similarity	NPC269586
0.9167	High Similarity	NPC32312
0.9123	High Similarity	NPC65873
0.9123	High Similarity	NPC212114
0.9123	High Similarity	NPC300345
0.9123	High Similarity	NPC120441
0.9107	High Similarity	NPC149436
0.9107	High Similarity	NPC277704
0.9016	High Similarity	NPC113837
0.9016	High Similarity	NPC289915
0.8983	High Similarity	NPC210849
0.8983	High Similarity	NPC54368
0.8983	High Similarity	NPC135924
0.8983	High Similarity	NPC248705
0.8966	High Similarity	NPC8235
0.8947	High Similarity	NPC198841
0.8871	High Similarity	NPC6107
0.8833	High Similarity	NPC29680
0.8814	High Similarity	NPC169110
0.8689	High Similarity	NPC88566
0.8667	High Similarity	NPC246588
0.8667	High Similarity	NPC310758
0.8667	High Similarity	NPC238023
0.8644	High Similarity	NPC114327
0.8644	High Similarity	NPC36357
0.8594	High Similarity	NPC246822
0.8594	High Similarity	NPC213570
0.8594	High Similarity	NPC139416
0.8548	High Similarity	NPC198023
0.8548	High Similarity	NPC155172
0.8413	Intermediate Similarity	NPC178527
0.8387	Intermediate Similarity	NPC113670
0.8333	Intermediate Similarity	NPC39799
0.8333	Intermediate Similarity	NPC226999
0.8333	Intermediate Similarity	NPC193578
0.8333	Intermediate Similarity	NPC280135
0.8333	Intermediate Similarity	NPC158028
0.8333	Intermediate Similarity	NPC1008
0.8333	Intermediate Similarity	NPC87099
0.8333	Intermediate Similarity	NPC135433
0.8281	Intermediate Similarity	NPC267443
0.8226	Intermediate Similarity	NPC200745
0.8226	Intermediate Similarity	NPC22786
0.8226	Intermediate Similarity	NPC66517
0.8226	Intermediate Similarity	NPC71009
0.8209	Intermediate Similarity	NPC54269
0.8182	Intermediate Similarity	NPC251490
0.8095	Intermediate Similarity	NPC21211
0.8065	Intermediate Similarity	NPC45255
0.7971	Intermediate Similarity	NPC307195
0.7969	Intermediate Similarity	NPC291066
0.7941	Intermediate Similarity	NPC1901
0.791	Intermediate Similarity	NPC72670
0.7903	Intermediate Similarity	NPC147578
0.7879	Intermediate Similarity	NPC311343
0.7857	Intermediate Similarity	NPC110264
0.7846	Intermediate Similarity	NPC36440
0.7826	Intermediate Similarity	NPC96835
0.7826	Intermediate Similarity	NPC258492
0.7812	Intermediate Similarity	NPC50266
0.7778	Intermediate Similarity	NPC200624
0.7761	Intermediate Similarity	NPC473206
0.7761	Intermediate Similarity	NPC98880
0.7746	Intermediate Similarity	NPC249018
0.7746	Intermediate Similarity	NPC3190
0.7692	Intermediate Similarity	NPC264470
0.7681	Intermediate Similarity	NPC212463
0.7647	Intermediate Similarity	NPC95289
0.7647	Intermediate Similarity	NPC263385
0.7612	Intermediate Similarity	NPC82770
0.7612	Intermediate Similarity	NPC78954
0.7612	Intermediate Similarity	NPC22760
0.7612	Intermediate Similarity	NPC239931
0.7536	Intermediate Similarity	NPC326200
0.7536	Intermediate Similarity	NPC74458
0.7534	Intermediate Similarity	NPC159661
0.75	Intermediate Similarity	NPC200936
0.75	Intermediate Similarity	NPC235059
0.75	Intermediate Similarity	NPC11150
0.75	Intermediate Similarity	NPC5324
0.75	Intermediate Similarity	NPC16190
0.75	Intermediate Similarity	NPC297358
0.75	Intermediate Similarity	NPC169222
0.7465	Intermediate Similarity	NPC276699
0.7465	Intermediate Similarity	NPC189371
0.7463	Intermediate Similarity	NPC52330
0.7432	Intermediate Similarity	NPC315216
0.7429	Intermediate Similarity	NPC285679
0.7397	Intermediate Similarity	NPC66270
0.7397	Intermediate Similarity	NPC255345
0.7397	Intermediate Similarity	NPC245896
0.7391	Intermediate Similarity	NPC229235
0.7333	Intermediate Similarity	NPC242628
0.7324	Intermediate Similarity	NPC122327
0.7324	Intermediate Similarity	NPC113000
0.7324	Intermediate Similarity	NPC112609
0.7286	Intermediate Similarity	NPC208302
0.7286	Intermediate Similarity	NPC155429
0.726	Intermediate Similarity	NPC290638
0.726	Intermediate Similarity	NPC298023
0.7222	Intermediate Similarity	NPC98976
0.72	Intermediate Similarity	NPC50063
0.7183	Intermediate Similarity	NPC244738
0.7183	Intermediate Similarity	NPC271437
0.7162	Intermediate Similarity	NPC224544
0.7162	Intermediate Similarity	NPC103488
0.7143	Intermediate Similarity	NPC219246
0.7123	Intermediate Similarity	NPC139658
0.7123	Intermediate Similarity	NPC175393
0.7123	Intermediate Similarity	NPC271642
0.7101	Intermediate Similarity	NPC181786
0.7083	Intermediate Similarity	NPC108218
0.7083	Intermediate Similarity	NPC208075
0.7051	Intermediate Similarity	NPC267704
0.7027	Intermediate Similarity	NPC98269
0.7027	Intermediate Similarity	NPC329318
0.7027	Intermediate Similarity	NPC3672
0.7027	Intermediate Similarity	NPC325662
0.7027	Intermediate Similarity	NPC287790
0.7027	Intermediate Similarity	NPC9796
0.6986	Remote Similarity	NPC206800
0.6986	Remote Similarity	NPC32203
0.6974	Remote Similarity	NPC190567
0.6974	Remote Similarity	NPC328178
0.6974	Remote Similarity	NPC17408
0.6974	Remote Similarity	NPC285716
0.6974	Remote Similarity	NPC157055
0.6933	Remote Similarity	NPC2785
0.6933	Remote Similarity	NPC12857
0.6933	Remote Similarity	NPC36342
0.6933	Remote Similarity	NPC285470
0.6933	Remote Similarity	NPC137847
0.6933	Remote Similarity	NPC76455
0.6933	Remote Similarity	NPC50192
0.6892	Remote Similarity	NPC302129
0.6883	Remote Similarity	NPC133050
0.6883	Remote Similarity	NPC145053
0.6883	Remote Similarity	NPC231986
0.6875	Remote Similarity	NPC164526
0.6875	Remote Similarity	NPC160339
0.6875	Remote Similarity	NPC307
0.6849	Remote Similarity	NPC299134
0.6842	Remote Similarity	NPC469894
0.6842	Remote Similarity	NPC272260
0.6842	Remote Similarity	NPC300205
0.6842	Remote Similarity	NPC170484
0.6842	Remote Similarity	NPC167577
0.6842	Remote Similarity	NPC78517
0.6806	Remote Similarity	NPC125144
0.6806	Remote Similarity	NPC121708
0.68	Remote Similarity	NPC179726
0.68	Remote Similarity	NPC245966
0.6795	Remote Similarity	NPC230068
0.679	Remote Similarity	NPC60408
0.6769	Remote Similarity	NPC469807
0.6753	Remote Similarity	NPC475573
0.6753	Remote Similarity	NPC95868
0.6753	Remote Similarity	NPC477703
0.6753	Remote Similarity	NPC164449
0.6753	Remote Similarity	NPC184030
0.6753	Remote Similarity	NPC475289
0.6753	Remote Similarity	NPC164086
0.6753	Remote Similarity	NPC121800
0.6711	Remote Similarity	NPC176228
0.6709	Remote Similarity	NPC197581
0.6709	Remote Similarity	NPC477770
0.6707	Remote Similarity	NPC111233
0.6707	Remote Similarity	NPC329064
0.6707	Remote Similarity	NPC153308
0.6667	Remote Similarity	NPC303245
0.6667	Remote Similarity	NPC12936
0.6667	Remote Similarity	NPC273033
0.6667	Remote Similarity	NPC89950
0.6667	Remote Similarity	NPC100039
0.6627	Remote Similarity	NPC298115
0.6627	Remote Similarity	NPC19680
0.6625	Remote Similarity	NPC304538
0.6625	Remote Similarity	NPC95429
0.6625	Remote Similarity	NPC168855
0.6625	Remote Similarity	NPC133162
0.6623	Remote Similarity	NPC151405
0.6623	Remote Similarity	NPC139901
0.6582	Remote Similarity	NPC87299
0.6582	Remote Similarity	NPC103387
0.6582	Remote Similarity	NPC323103
0.6582	Remote Similarity	NPC73637
0.6582	Remote Similarity	NPC106313
0.6582	Remote Similarity	NPC121478
0.6582	Remote Similarity	NPC329319
0.6582	Remote Similarity	NPC103326
0.6582	Remote Similarity	NPC14326
0.6582	Remote Similarity	NPC99394
0.6582	Remote Similarity	NPC99240
0.6579	Remote Similarity	NPC66655
0.6548	Remote Similarity	NPC26224
0.6548	Remote Similarity	NPC277277
0.6548	Remote Similarity	NPC70436

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 NPC64270 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	943
0.1-0.2	827
0.2-0.3	3226
0.3-0.4	2745
0.4-0.5	984
0.5-0.6	309
0.6-0.7	107
0.7-0.8	8
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8387	Intermediate Similarity	NPD675	Discontinued
0.7969	Intermediate Similarity	NPD173	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD292	Approved
0.7794	Intermediate Similarity	NPD294	Approved
0.75	Intermediate Similarity	NPD1673	Approved
0.75	Intermediate Similarity	NPD9497	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD9590	Approved
0.7324	Intermediate Similarity	NPD9594	Approved
0.7324	Intermediate Similarity	NPD9591	Approved
0.7324	Intermediate Similarity	NPD9593	Approved
0.7324	Intermediate Similarity	NPD9592	Approved
0.7324	Intermediate Similarity	NPD9589	Approved
0.7324	Intermediate Similarity	NPD80	Approved
0.7324	Intermediate Similarity	NPD9588	Approved
0.7183	Intermediate Similarity	NPD9728	Phase 1
0.7083	Intermediate Similarity	NPD505	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD589	Approved
0.7067	Intermediate Similarity	NPD590	Approved
0.7027	Intermediate Similarity	NPD603	Approved
0.7027	Intermediate Similarity	NPD4144	Approved
0.7027	Intermediate Similarity	NPD4147	Approved
0.6986	Remote Similarity	NPD9716	Approved
0.6974	Remote Similarity	NPD3979	Approved
0.6974	Remote Similarity	NPD260	Discontinued
0.6974	Remote Similarity	NPD3904	Approved
0.6974	Remote Similarity	NPD3981	Approved
0.6974	Remote Similarity	NPD3903	Approved
0.6962	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD79	Approved
0.6933	Remote Similarity	NPD9564	Approved
0.6933	Remote Similarity	NPD296	Approved
0.6933	Remote Similarity	NPD295	Approved
0.6933	Remote Similarity	NPD9563	Approved
0.6933	Remote Similarity	NPD293	Approved
0.6883	Remote Similarity	NPD4026	Approved
0.6883	Remote Similarity	NPD4027	Approved
0.6883	Remote Similarity	NPD3035	Approved
0.6875	Remote Similarity	NPD3099	Discontinued
0.6842	Remote Similarity	NPD508	Approved
0.6842	Remote Similarity	NPD507	Approved
0.6842	Remote Similarity	NPD1051	Approved
0.6842	Remote Similarity	NPD1053	Approved
0.6842	Remote Similarity	NPD1052	Approved
0.6842	Remote Similarity	NPD1475	Approved
0.6835	Remote Similarity	NPD4544	Approved
0.6795	Remote Similarity	NPD4170	Approved
0.6795	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4169	Approved
0.679	Remote Similarity	NPD782	Approved
0.679	Remote Similarity	NPD781	Approved
0.679	Remote Similarity	NPD783	Approved
0.679	Remote Similarity	NPD780	Approved
0.6753	Remote Similarity	NPD1617	Discontinued
0.6753	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5372	Approved
0.6753	Remote Similarity	NPD5371	Approved
0.6711	Remote Similarity	NPD9397	Approved
0.6711	Remote Similarity	NPD225	Approved
0.6711	Remote Similarity	NPD9393	Approved
0.6711	Remote Similarity	NPD227	Approved
0.6709	Remote Similarity	NPD4635	Approved
0.6709	Remote Similarity	NPD263	Approved
0.6709	Remote Similarity	NPD262	Approved
0.6709	Remote Similarity	NPD2001	Discontinued
0.6667	Remote Similarity	NPD942	Approved
0.6667	Remote Similarity	NPD472	Approved
0.6625	Remote Similarity	NPD3427	Approved
0.6625	Remote Similarity	NPD3429	Approved
0.6625	Remote Similarity	NPD5178	Approved
0.6579	Remote Similarity	NPD9294	Approved
0.6543	Remote Similarity	NPD2205	Approved
0.6543	Remote Similarity	NPD2208	Approved
0.6543	Remote Similarity	NPD5916	Discontinued
0.6538	Remote Similarity	NPD914	Suspended
0.65	Remote Similarity	NPD830	Approved
0.65	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1185	Approved
0.65	Remote Similarity	NPD831	Approved
0.65	Remote Similarity	NPD1800	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3971	Phase 1
0.6463	Remote Similarity	NPD4406	Approved
0.6463	Remote Similarity	NPD4409	Approved
0.6463	Remote Similarity	NPD4636	Approved
0.6456	Remote Similarity	NPD226	Approved
0.6452	Remote Similarity	NPD9072	Clinical (unspecified phase)
0.642	Remote Similarity	NPD9395	Approved
0.642	Remote Similarity	NPD2538	Approved
0.642	Remote Similarity	NPD785	Approved
0.642	Remote Similarity	NPD2539	Approved
0.641	Remote Similarity	NPD9490	Approved
0.6395	Remote Similarity	NPD4407	Approved
0.6395	Remote Similarity	NPD4405	Approved
0.6395	Remote Similarity	NPD4408	Approved
0.6386	Remote Similarity	NPD1087	Approved
0.6386	Remote Similarity	NPD2002	Discontinued
0.6386	Remote Similarity	NPD650	Approved
0.6386	Remote Similarity	NPD3426	Approved
0.6386	Remote Similarity	NPD4146	Approved
0.6386	Remote Similarity	NPD3428	Approved
0.6386	Remote Similarity	NPD4145	Approved
0.6322	Remote Similarity	NPD4542	Approved
0.6322	Remote Similarity	NPD845	Approved
0.6322	Remote Similarity	NPD4545	Approved
0.631	Remote Similarity	NPD1101	Approved
0.631	Remote Similarity	NPD5675	Discontinued
0.631	Remote Similarity	NPD3345	Approved
0.6296	Remote Similarity	NPD4000	Phase 3
0.6296	Remote Similarity	NPD9491	Approved
0.6279	Remote Similarity	NPD7609	Phase 3
0.6265	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6049	Phase 2
0.625	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD5346	Phase 2
0.6235	Remote Similarity	NPD5347	Phase 2
0.6235	Remote Similarity	NPD771	Phase 3
0.6235	Remote Similarity	NPD5656	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD800	Approved
0.6207	Remote Similarity	NPD7631	Approved
0.6207	Remote Similarity	NPD159	Clinical (unspecified phase)
0.619	Remote Similarity	NPD1282	Approved
0.619	Remote Similarity	NPD4793	Discontinued
0.619	Remote Similarity	NPD506	Clinical (unspecified phase)
0.618	Remote Similarity	NPD3093	Approved
0.618	Remote Similarity	NPD1809	Phase 2
0.6163	Remote Similarity	NPD3346	Approved
0.6163	Remote Similarity	NPD3673	Approved
0.6163	Remote Similarity	NPD1086	Approved
0.6163	Remote Similarity	NPD4728	Approved
0.6163	Remote Similarity	NPD3344	Approved
0.6163	Remote Similarity	NPD2811	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD5915	Approved
0.6163	Remote Similarity	NPD3672	Approved
0.6163	Remote Similarity	NPD1090	Approved
0.6163	Remote Similarity	NPD1089	Approved
0.6145	Remote Similarity	NPD111	Approved
0.6145	Remote Similarity	NPD9505	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD2878	Approved
0.6136	Remote Similarity	NPD3980	Approved
0.6136	Remote Similarity	NPD3982	Approved
0.6118	Remote Similarity	NPD587	Approved
0.6118	Remote Similarity	NPD588	Approved
0.6118	Remote Similarity	NPD531	Approved
0.6111	Remote Similarity	NPD5598	Approved
0.6111	Remote Similarity	NPD3495	Discontinued
0.6111	Remote Similarity	NPD5597	Approved
0.6098	Remote Similarity	NPD423	Phase 3
0.6092	Remote Similarity	NPD2997	Approved
0.6092	Remote Similarity	NPD3000	Approved
0.6092	Remote Similarity	NPD530	Approved
0.6092	Remote Similarity	NPD2998	Approved
0.6092	Remote Similarity	NPD4543	Discontinued
0.6092	Remote Similarity	NPD517	Discontinued
0.6071	Remote Similarity	NPD305	Approved
0.6071	Remote Similarity	NPD1697	Approved
0.6071	Remote Similarity	NPD304	Approved
0.6067	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD9250	Approved
0.6047	Remote Similarity	NPD1629	Approved
0.6047	Remote Similarity	NPD1628	Approved
0.6047	Remote Similarity	NPD297	Approved
0.6047	Remote Similarity	NPD9	Approved
0.6023	Remote Similarity	NPD752	Approved
0.6023	Remote Similarity	NPD1088	Approved
0.6	Remote Similarity	NPD187	Approved
0.6	Remote Similarity	NPD1738	Approved
0.6	Remote Similarity	NPD2895	Discontinued
0.6	Remote Similarity	NPD9538	Approved
0.6	Remote Similarity	NPD6472	Discontinued
0.5955	Remote Similarity	NPD3719	Approved
0.5955	Remote Similarity	NPD719	Approved
0.5955	Remote Similarity	NPD1563	Approved
0.5955	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD720	Approved
0.5955	Remote Similarity	NPD1409	Phase 3
0.5955	Remote Similarity	NPD3718	Approved
0.5934	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD713	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD6354	Discontinued
0.5909	Remote Similarity	NPD1007	Discontinued
0.5909	Remote Similarity	NPD1239	Approved
0.5889	Remote Similarity	NPD4094	Approved
0.5889	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD5554	Approved
0.5889	Remote Similarity	NPD2655	Approved
0.5889	Remote Similarity	NPD7344	Phase 1
0.5889	Remote Similarity	NPD4814	Discontinued
0.5889	Remote Similarity	NPD7343	Discovery
0.5889	Remote Similarity	NPD1693	Approved
0.5889	Remote Similarity	NPD2656	Approved
0.587	Remote Similarity	NPD5832	Phase 3
0.5862	Remote Similarity	NPD9349	Approved
0.5862	Remote Similarity	NPD9350	Approved
0.5862	Remote Similarity	NPD9351	Phase 3
0.5862	Remote Similarity	NPD9348	Approved
0.5862	Remote Similarity	NPD689	Discontinued
0.5851	Remote Similarity	NPD813	Approved
0.5851	Remote Similarity	NPD1419	Approved
0.5851	Remote Similarity	NPD1417	Approved
0.5843	Remote Similarity	NPD1812	Approved
0.5843	Remote Similarity	NPD1814	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