NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	194.06
Volume:	194.938
LogP:	1.671
LogD:	4.047
LogS:	-1.975
# Rotatable Bonds:	4
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.665
Synthetic Accessibility Score:	1.487
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.454
MDCK Permeability:	3.9486480090999976e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.058
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.848
Plasma Protein Binding (PPB):	38.08927917480469%
Volume Distribution (VD):	0.949
Pgp-substrate:	30.11492156982422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.903
CYP2C19-inhibitor:	0.928
CYP2C19-substrate:	0.261
CYP2C9-inhibitor:	0.488
CYP2C9-substrate:	0.819
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.396
CYP3A4-inhibitor:	0.078
CYP3A4-substrate:	0.204

ADMET: Excretion

Clearance (CL):	11.138
Half-life (T1/2):	0.775

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.041
Drug-inuced Liver Injury (DILI):	0.634
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.278
Carcinogencity:	0.023
Eye Corrosion:	0.028
Eye Irritation:	0.99
Respiratory Toxicity:	0.048

Download Data

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

Natural Product: NPC31786

Natural Product ID:	NPC31786
*Common Name:**	Dimethyl Phthalate
IUPAC Name:	dimethyl benzene-1,2-dicarboxylate
Synonyms:	Dimethyl Phthalate; Dimethylphthalate; Methyl Phthalate
Standard InCHIKey:	NIQCNGHVCWTJSM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H10O4/c1-13-9(11)7-5-3-4-6-8(7)10(12)14-2/h3-6H,1-2H3
SMILES:	COC(=O)c1ccccc1C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL323348
PubChem CID:	8554
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

*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
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562834]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[18177011]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	root	n.a.	PMID[18975262]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19271742]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20590154]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[24155209]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24333010]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24959987]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25302569]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8064299]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO7611	Sclerotium poriae cocos	Species	Typhulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11045	Paederia scandens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11045	Paederia scandens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7611	Sclerotium poriae cocos	Species	Typhulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11045	Paederia scandens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28251	Typha orientalis	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11045	Paederia scandens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15462	Angelica sinensis	Species	Apiaceae	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	12
Others	8
Potency	21

Activity Type	# Activity
Individual Protein	9
Others	32

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT246	Individual Protein	Dopamine transporter	Homo sapiens	IC50	>	100000.0	nM	PMID[474947]
NPT295	Individual Protein	Serotonin transporter	Homo sapiens	IC50	>	100000.0	nM	PMID[474947]
NPT546	Individual Protein	Retinoid X receptor alpha	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[474950]
NPT249	Individual Protein	Glucocorticoid receptor	Homo sapiens	Potency	n.a.	1000.0	nM	PMID[474951]
NPT249	Individual Protein	Glucocorticoid receptor	Homo sapiens	Potency	n.a.	446.7	nM	PMID[474950]
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[474950]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	2.5	nM	PMID[474950]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	22006.3	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	196.1	nM	PubChem BioAssay data set
NPT27	Others	Unspecified		Papp	=	43.32	10^-6 cm/s	PMID[474948]
NPT27	Others	Unspecified		Papp	=	157.68	10^-6 cm/s	PMID[474948]
NPT27	Others	Unspecified		LogP app	=	-3.8	n.a.	PMID[474948]
NPT35	Others	n.a.		LogP	=	1.56	n.a.	PMID[474948]
NPT27	Others	Unspecified		LogP app	=	-4.36	n.a.	PMID[474948]
NPT27	Others	Unspecified		R%	=	13.0	%	PMID[474948]
NPT35	Others	n.a.		LogP	=	1.61	n.a.	PMID[474949]
NPT2	Others	Unspecified		IC50	n.a.	20000.0	nM	PMID[474952]
NPT2	Others	Unspecified		IC50	n.a.	10000.0	nM	PMID[474952]
NPT35	Others	n.a.		LogP	=	1.59	n.a.	PMID[474953]
NPT2	Others	Unspecified		Potency	n.a.	27472.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	244.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1096.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24541.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	2730.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	174.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	22006.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	69008.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	774.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	38895.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	49265.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	38.6	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 NPC31786 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	254
0.1-0.2	1470
0.2-0.3	3891
0.3-0.4	9653
0.4-0.5	11160
0.5-0.6	11588
0.6-0.7	4111
0.7-0.8	490
0.8-0.85	32
0.85-0.9	23
0.9-0.95	15
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9796	High Similarity	NPC119271
0.9697	High Similarity	NPC56493
0.96	High Similarity	NPC17417
0.96	High Similarity	NPC10251
0.96	High Similarity	NPC85493
0.9505	High Similarity	NPC251854
0.9505	High Similarity	NPC174099
0.9505	High Similarity	NPC93084
0.9505	High Similarity	NPC196246
0.9505	High Similarity	NPC214067
0.9412	High Similarity	NPC305912
0.9412	High Similarity	NPC260818
0.9412	High Similarity	NPC1082
0.932	High Similarity	NPC270699
0.932	High Similarity	NPC321852
0.932	High Similarity	NPC82899
0.9192	High Similarity	NPC45613
0.9167	High Similarity	NPC130398
0.9143	High Similarity	NPC153053
0.91	High Similarity	NPC89886
0.9029	High Similarity	NPC265407
0.9029	High Similarity	NPC83628
0.902	High Similarity	NPC37622
0.902	High Similarity	NPC30594
0.899	High Similarity	NPC203925
0.898	High Similarity	NPC92754
0.898	High Similarity	NPC276775
0.898	High Similarity	NPC249912
0.8962	High Similarity	NPC307651
0.8922	High Similarity	NPC209632
0.8911	High Similarity	NPC60679
0.89	High Similarity	NPC282895
0.8889	High Similarity	NPC225060
0.8889	High Similarity	NPC35448
0.8889	High Similarity	NPC78701
0.8824	High Similarity	NPC114594
0.88	High Similarity	NPC146351
0.8725	High Similarity	NPC301943
0.8725	High Similarity	NPC474365
0.8713	High Similarity	NPC70624
0.8713	High Similarity	NPC42211
0.87	High Similarity	NPC229242
0.8679	High Similarity	NPC474157
0.8679	High Similarity	NPC210089
0.8667	High Similarity	NPC269023
0.8667	High Similarity	NPC99846
0.8627	High Similarity	NPC188895
0.8624	High Similarity	NPC149691
0.8614	High Similarity	NPC325497
0.8614	High Similarity	NPC118343
0.8532	High Similarity	NPC210092
0.8519	High Similarity	NPC272524
0.8505	High Similarity	NPC167504
0.8491	Intermediate Similarity	NPC469636
0.8447	Intermediate Similarity	NPC284477
0.844	Intermediate Similarity	NPC237366
0.844	Intermediate Similarity	NPC308744
0.8426	Intermediate Similarity	NPC79496
0.8381	Intermediate Similarity	NPC269457
0.8364	Intermediate Similarity	NPC474685
0.8333	Intermediate Similarity	NPC318107
0.8318	Intermediate Similarity	NPC474364
0.83	Intermediate Similarity	NPC261181
0.8265	Intermediate Similarity	NPC173443
0.8198	Intermediate Similarity	NPC306740
0.819	Intermediate Similarity	NPC255676
0.8182	Intermediate Similarity	NPC161611
0.8182	Intermediate Similarity	NPC128368
0.8165	Intermediate Similarity	NPC243355
0.8125	Intermediate Similarity	NPC100353
0.8108	Intermediate Similarity	NPC477411
0.8108	Intermediate Similarity	NPC196075
0.8108	Intermediate Similarity	NPC474363
0.8095	Intermediate Similarity	NPC304873
0.8091	Intermediate Similarity	NPC212415
0.8077	Intermediate Similarity	NPC217621
0.8061	Intermediate Similarity	NPC89377
0.8058	Intermediate Similarity	NPC253423
0.8056	Intermediate Similarity	NPC470391
0.8051	Intermediate Similarity	NPC246166
0.8036	Intermediate Similarity	NPC81808
0.8021	Intermediate Similarity	NPC288903
0.8018	Intermediate Similarity	NPC13784
0.8018	Intermediate Similarity	NPC474176
0.8	Intermediate Similarity	NPC476003
0.8	Intermediate Similarity	NPC62765
0.7965	Intermediate Similarity	NPC226093
0.7961	Intermediate Similarity	NPC61944
0.7931	Intermediate Similarity	NPC473243
0.7928	Intermediate Similarity	NPC158282
0.7928	Intermediate Similarity	NPC474314
0.7925	Intermediate Similarity	NPC25458
0.79	Intermediate Similarity	NPC220893
0.7899	Intermediate Similarity	NPC295664
0.7885	Intermediate Similarity	NPC270654
0.7881	Intermediate Similarity	NPC46634
0.7881	Intermediate Similarity	NPC223351
0.7876	Intermediate Similarity	NPC228936
0.787	Intermediate Similarity	NPC105899
0.7863	Intermediate Similarity	NPC50872
0.7857	Intermediate Similarity	NPC294134
0.7857	Intermediate Similarity	NPC58616
0.7845	Intermediate Similarity	NPC204784
0.7833	Intermediate Similarity	NPC121272
0.783	Intermediate Similarity	NPC473325
0.783	Intermediate Similarity	NPC112552
0.7826	Intermediate Similarity	NPC240664
0.7826	Intermediate Similarity	NPC228318
0.7818	Intermediate Similarity	NPC318327
0.7807	Intermediate Similarity	NPC135730
0.78	Intermediate Similarity	NPC304760
0.7769	Intermediate Similarity	NPC51292
0.7769	Intermediate Similarity	NPC169913
0.7768	Intermediate Similarity	NPC66208
0.7745	Intermediate Similarity	NPC119631
0.7736	Intermediate Similarity	NPC228435
0.7727	Intermediate Similarity	NPC249811
0.7727	Intermediate Similarity	NPC211439
0.7719	Intermediate Similarity	NPC474095
0.7686	Intermediate Similarity	NPC476599
0.7686	Intermediate Similarity	NPC275576
0.7679	Intermediate Similarity	NPC291799
0.7672	Intermediate Similarity	NPC469574
0.7667	Intermediate Similarity	NPC228739
0.7652	Intermediate Similarity	NPC188907
0.7652	Intermediate Similarity	NPC220540
0.7636	Intermediate Similarity	NPC1065
0.7615	Intermediate Similarity	NPC329282
0.7615	Intermediate Similarity	NPC85977
0.7611	Intermediate Similarity	NPC23332
0.7586	Intermediate Similarity	NPC128825
0.7586	Intermediate Similarity	NPC158157
0.7586	Intermediate Similarity	NPC131192
0.7583	Intermediate Similarity	NPC472703
0.7573	Intermediate Similarity	NPC110704
0.7565	Intermediate Similarity	NPC470764
0.7565	Intermediate Similarity	NPC474408
0.7565	Intermediate Similarity	NPC186933
0.7563	Intermediate Similarity	NPC144547
0.7561	Intermediate Similarity	NPC45537
0.7561	Intermediate Similarity	NPC115797
0.7561	Intermediate Similarity	NPC51448
0.7525	Intermediate Similarity	NPC322387
0.7523	Intermediate Similarity	NPC234305
0.7522	Intermediate Similarity	NPC183648
0.7522	Intermediate Similarity	NPC474057
0.7521	Intermediate Similarity	NPC471466
0.7521	Intermediate Similarity	NPC217423
0.7521	Intermediate Similarity	NPC472704
0.7521	Intermediate Similarity	NPC45104
0.7521	Intermediate Similarity	NPC182646
0.75	Intermediate Similarity	NPC281604
0.7479	Intermediate Similarity	NPC289432
0.7479	Intermediate Similarity	NPC230951
0.7479	Intermediate Similarity	NPC988
0.7476	Intermediate Similarity	NPC213156
0.7476	Intermediate Similarity	NPC240108
0.7475	Intermediate Similarity	NPC285773
0.7475	Intermediate Similarity	NPC39600
0.746	Intermediate Similarity	NPC472394
0.7459	Intermediate Similarity	NPC470163
0.7459	Intermediate Similarity	NPC470162
0.7458	Intermediate Similarity	NPC27633
0.7458	Intermediate Similarity	NPC94298
0.7458	Intermediate Similarity	NPC94637
0.7456	Intermediate Similarity	NPC54626
0.7455	Intermediate Similarity	NPC269644
0.744	Intermediate Similarity	NPC147561
0.744	Intermediate Similarity	NPC272946
0.744	Intermediate Similarity	NPC42234
0.7438	Intermediate Similarity	NPC217756
0.7436	Intermediate Similarity	NPC470860
0.7434	Intermediate Similarity	NPC234639
0.7434	Intermediate Similarity	NPC273837
0.7431	Intermediate Similarity	NPC320891
0.7431	Intermediate Similarity	NPC222390
0.7431	Intermediate Similarity	NPC244427
0.7422	Intermediate Similarity	NPC311339
0.7414	Intermediate Similarity	NPC221275
0.7414	Intermediate Similarity	NPC476357
0.7407	Intermediate Similarity	NPC98911
0.7407	Intermediate Similarity	NPC472318
0.74	Intermediate Similarity	NPC44546
0.7398	Intermediate Similarity	NPC470765
0.7396	Intermediate Similarity	NPC287790
0.7396	Intermediate Similarity	NPC3672
0.7395	Intermediate Similarity	NPC61779
0.7395	Intermediate Similarity	NPC90522
0.7395	Intermediate Similarity	NPC328459
0.7391	Intermediate Similarity	NPC17693
0.7383	Intermediate Similarity	NPC156021
0.7381	Intermediate Similarity	NPC470278
0.7379	Intermediate Similarity	NPC9822
0.7377	Intermediate Similarity	NPC51079
0.7377	Intermediate Similarity	NPC85511
0.7374	Intermediate Similarity	NPC323103
0.7364	Intermediate Similarity	NPC274443
0.7364	Intermediate Similarity	NPC329556
0.7364	Intermediate Similarity	NPC160382
0.7353	Intermediate Similarity	NPC43945

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 NPC31786 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	934
0.2-0.3	1310
0.3-0.4	2881
0.4-0.5	2301
0.5-0.6	1140
0.6-0.7	282
0.7-0.8	52
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD164	Approved
0.96	High Similarity	NPD2182	Approved
0.8857	High Similarity	NPD2181	Clinical (unspecified phase)
0.8614	High Similarity	NPD1238	Approved
0.8333	Intermediate Similarity	NPD9257	Approved
0.8333	Intermediate Similarity	NPD9259	Approved
0.83	Intermediate Similarity	NPD1202	Approved
0.8103	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.8091	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD9258	Approved
0.8	Intermediate Similarity	NPD9256	Approved
0.7818	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD9260	Approved
0.7604	Intermediate Similarity	NPD9490	Approved
0.7589	Intermediate Similarity	NPD2067	Discontinued
0.7586	Intermediate Similarity	NPD9493	Approved
0.7565	Intermediate Similarity	NPD5951	Approved
0.7525	Intermediate Similarity	NPD1087	Approved
0.75	Intermediate Similarity	NPD6287	Discontinued
0.7475	Intermediate Similarity	NPD9491	Approved
0.7458	Intermediate Similarity	NPD9545	Approved
0.744	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD1929	Approved
0.7364	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD1930	Approved
0.7353	Intermediate Similarity	NPD650	Approved
0.7333	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD227	Approved
0.732	Intermediate Similarity	NPD225	Approved
0.7317	Intermediate Similarity	NPD1876	Approved
0.7315	Intermediate Similarity	NPD9495	Approved
0.7308	Intermediate Similarity	NPD1090	Approved
0.7308	Intermediate Similarity	NPD1086	Approved
0.7308	Intermediate Similarity	NPD1089	Approved
0.7302	Intermediate Similarity	NPD7008	Discontinued
0.7297	Intermediate Similarity	NPD1237	Approved
0.729	Intermediate Similarity	NPD1989	Approved
0.7273	Intermediate Similarity	NPD1932	Approved
0.7248	Intermediate Similarity	NPD2066	Phase 3
0.7244	Intermediate Similarity	NPD3764	Approved
0.7212	Intermediate Similarity	NPD800	Approved
0.7207	Intermediate Similarity	NPD9261	Approved
0.72	Intermediate Similarity	NPD1019	Discontinued
0.7196	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1241	Discontinued
0.717	Intermediate Similarity	NPD1088	Approved
0.7154	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD3672	Approved
0.7143	Intermediate Similarity	NPD5909	Discontinued
0.7143	Intermediate Similarity	NPD3673	Approved
0.7103	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1563	Approved
0.71	Intermediate Similarity	NPD226	Approved
0.7097	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD5277	Phase 2
0.7087	Intermediate Similarity	NPD6832	Phase 2
0.7075	Intermediate Similarity	NPD7609	Phase 3
0.7075	Intermediate Similarity	NPD1239	Approved
0.7073	Intermediate Similarity	NPD1281	Approved
0.7068	Intermediate Similarity	NPD2346	Discontinued
0.7054	Intermediate Similarity	NPD6647	Phase 2
0.7043	Intermediate Similarity	NPD2329	Discontinued
0.704	Intermediate Similarity	NPD2198	Approved
0.704	Intermediate Similarity	NPD2199	Approved
0.7037	Intermediate Similarity	NPD1693	Approved
0.7016	Intermediate Similarity	NPD3972	Approved
0.7009	Intermediate Similarity	NPD9508	Approved
0.7009	Intermediate Similarity	NPD7631	Approved
0.7	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD9567	Approved
0.6984	Remote Similarity	NPD552	Approved
0.6984	Remote Similarity	NPD553	Approved
0.6983	Remote Similarity	NPD1317	Discontinued
0.6977	Remote Similarity	NPD2313	Discontinued
0.6957	Remote Similarity	NPD9263	Approved
0.6957	Remote Similarity	NPD1358	Approved
0.6957	Remote Similarity	NPD9264	Approved
0.6957	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9267	Approved
0.6942	Remote Similarity	NPD2347	Approved
0.694	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1564	Approved
0.6909	Remote Similarity	NPD1565	Approved
0.6909	Remote Similarity	NPD1566	Phase 3
0.6905	Remote Similarity	NPD1283	Approved
0.6897	Remote Similarity	NPD74	Approved
0.6897	Remote Similarity	NPD9266	Approved
0.687	Remote Similarity	NPD3134	Approved
0.6857	Remote Similarity	NPD1282	Approved
0.6852	Remote Similarity	NPD1508	Approved
0.685	Remote Similarity	NPD1203	Approved
0.6818	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD447	Suspended
0.6818	Remote Similarity	NPD230	Phase 1
0.68	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2798	Approved
0.6796	Remote Similarity	NPD3971	Phase 1
0.6791	Remote Similarity	NPD2799	Discontinued
0.6791	Remote Similarity	NPD3748	Approved
0.678	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD17	Approved
0.6774	Remote Similarity	NPD1104	Approved
0.6765	Remote Similarity	NPD942	Approved
0.6746	Remote Similarity	NPD6637	Approved
0.6742	Remote Similarity	NPD2979	Phase 3
0.6742	Remote Similarity	NPD4307	Phase 2
0.6742	Remote Similarity	NPD3373	Approved
0.6741	Remote Similarity	NPD2935	Discontinued
0.6729	Remote Similarity	NPD5347	Phase 2
0.6729	Remote Similarity	NPD5346	Phase 2
0.6723	Remote Similarity	NPD969	Suspended
0.6719	Remote Similarity	NPD3266	Approved
0.6719	Remote Similarity	NPD1470	Approved
0.6719	Remote Similarity	NPD3267	Approved
0.6716	Remote Similarity	NPD2567	Approved
0.6716	Remote Similarity	NPD2569	Approved
0.6698	Remote Similarity	NPD4793	Discontinued
0.6696	Remote Similarity	NPD5926	Approved
0.6695	Remote Similarity	NPD5235	Approved
0.6695	Remote Similarity	NPD5236	Approved
0.6695	Remote Similarity	NPD5237	Approved
0.6695	Remote Similarity	NPD5239	Approved
0.6695	Remote Similarity	NPD5240	Approved
0.6694	Remote Similarity	NPD2629	Approved
0.6694	Remote Similarity	NPD5691	Approved
0.6694	Remote Similarity	NPD1651	Approved
0.6694	Remote Similarity	NPD9281	Approved
0.6692	Remote Similarity	NPD1933	Approved
0.6691	Remote Similarity	NPD7236	Approved
0.6691	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD1471	Phase 3
0.6667	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1843	Approved
0.6667	Remote Similarity	NPD6085	Phase 2
0.6667	Remote Similarity	NPD9716	Approved
0.6643	Remote Similarity	NPD3226	Approved
0.6642	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD5667	Approved
0.664	Remote Similarity	NPD4626	Approved
0.664	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4198	Discontinued
0.6639	Remote Similarity	NPD2201	Approved
0.6638	Remote Similarity	NPD9697	Approved
0.6614	Remote Similarity	NPD1608	Approved
0.6614	Remote Similarity	NPD4878	Approved
0.6614	Remote Similarity	NPD1481	Phase 2
0.6613	Remote Similarity	NPD1894	Discontinued
0.6609	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3495	Discontinued
0.6591	Remote Similarity	NPD411	Approved
0.6591	Remote Similarity	NPD9471	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD2797	Approved
0.6587	Remote Similarity	NPD1889	Phase 1
0.6587	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.656	Remote Similarity	NPD5585	Approved
0.6557	Remote Similarity	NPD1246	Approved
0.6555	Remote Similarity	NPD1752	Approved
0.6555	Remote Similarity	NPD4233	Approved
0.6555	Remote Similarity	NPD1756	Approved
0.6555	Remote Similarity	NPD4234	Approved
0.6549	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD4628	Phase 3
0.6547	Remote Similarity	NPD3750	Approved
0.6544	Remote Similarity	NPD4308	Phase 3
0.6542	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7713	Phase 3
0.6535	Remote Similarity	NPD1535	Discovery
0.6528	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD6039	Approved
0.6508	Remote Similarity	NPD5306	Approved
0.6508	Remote Similarity	NPD5305	Approved
0.6491	Remote Similarity	NPD7798	Approved
0.6489	Remote Similarity	NPD9494	Approved
0.6484	Remote Similarity	NPD1877	Discontinued
0.6475	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2670	Approved
0.6466	Remote Similarity	NPD3268	Approved
0.6462	Remote Similarity	NPD1164	Approved
0.6458	Remote Similarity	NPD7239	Suspended
0.6457	Remote Similarity	NPD4135	Approved
0.6457	Remote Similarity	NPD4106	Approved
0.6457	Remote Similarity	NPD4136	Approved
0.6457	Remote Similarity	NPD3847	Discontinued
0.6457	Remote Similarity	NPD3496	Discontinued
0.6452	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7611	Approved
0.6449	Remote Similarity	NPD2353	Approved
0.6449	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4618	Approved
0.6444	Remote Similarity	NPD4622	Approved
0.6434	Remote Similarity	NPD6273	Approved
0.6429	Remote Similarity	NPD1245	Approved
0.6429	Remote Similarity	NPD9268	Approved
0.6429	Remote Similarity	NPD4105	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