NPASS Compound

Structure

CID291049 OpenBabel06191716102D 26 27 0 0 0 0 0 0 0 0999 V2000 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 25 1 0 0 0 0 6 9 2 0 0 0 0 6 12 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 12 2 0 0 0 0 10 17 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 16 2 0 0 0 0 14 18 1 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.12
Volume:	360.507
LogP:	4.804
LogD:	2.92
LogS:	-3.912
# Rotatable Bonds:	5
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.566
Synthetic Accessibility Score:	2.586
Fsp3:	0.263
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.29
MDCK Permeability:	8.78456648933934e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.24
Human Intestinal Absorption (HIA):	0.066
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	98.69070434570312%
Volume Distribution (VD):	0.349
Pgp-substrate:	1.3249123096466064%

ADMET: Metabolism

CYP1A2-inhibitor:	0.083
CYP1A2-substrate:	0.919
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.464
CYP2C9-substrate:	0.101
CYP2D6-inhibitor:	0.092
CYP2D6-substrate:	0.136
CYP3A4-inhibitor:	0.049
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	3.194
Half-life (T1/2):	0.843

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.094
Drug-inuced Liver Injury (DILI):	0.865
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.623
Maximum Recommended Daily Dose:	0.126
Skin Sensitization:	0.456
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.854
Respiratory Toxicity:	0.675

Download Data

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

Natural Product: NPC291049

Natural Product ID:	NPC291049
*Common Name:**	2-Hydroxy-4-(2-Hydroxy-4-Methoxy-3,6-Dimethylbenzoyl)Oxy-3,6-Dimethylbenzoic Acid
IUPAC Name:	2-hydroxy-4-(2-hydroxy-4-methoxy-3,6-dimethylbenzoyl)oxy-3,6-dimethylbenzoic acid
Synonyms:
Standard InCHIKey:	NMKBRSYSHBPUPY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H20O7/c1-8-7-13(11(4)16(20)14(8)18(22)23)26-19(24)15-9(2)6-12(25-5)10(3)17(15)21/h6-7,20-21H,1-5H3,(H,22,23)/p-1
SMILES:	Cc1cc(c(C)c(c1C(=O)O)[O-])OC(=O)c1c(C)cc(c(C)c1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1902081
PubChem CID:	167666
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO12551	Entada pursaetha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124758]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16748484]
NPO20034	Hyattella intestinalis	Species	Spongiidae	Eukaryota	n.a.	Inner Gneerings, a group of shoals off Mooloolaba (Australia)	2005-JUL	PMID[17125226]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20597533]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23656415]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25650289]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Bulb	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2602	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2602	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20034	Hyattella intestinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18734	Bouvardia ternifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22985	Thamnosma montana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16394	Coniocarpon cinnabarinum	Species	Arthoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14925	Eucomis comosa	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17779	Lycopodium clavatum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22141	Senecio macrospermus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24220	Inocybe umbrina	Species	Inocybaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23347	Piper fadyenii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22838	Ardisia gigantifolia	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2602	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12551	Entada pursaetha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17038	Linum sativum	Species	Linaceae	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
Potency	13

Activity Type	# Activity
Cell Line	1
Individual Protein	11
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[518922]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[518922]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[518922]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	920.0	nM	PMID[518922]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[518922]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[518922]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[518922]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[518922]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[518922]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[518922]
NPT2	Others	Unspecified		Potency	n.a.	794.3	nM	PMID[518922]
NPT920	Individual Protein	Alpha-synuclein	Homo sapiens	Potency	n.a.	5623.4	nM	PMID[518922]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	Potency	n.a.	23778.1	nM	PMID[518922]

☑ 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 NPC291049 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	362
0.1-0.2	1725
0.2-0.3	4031
0.3-0.4	9536
0.4-0.5	8706
0.5-0.6	3525
0.6-0.7	5376
0.7-0.8	6006
0.8-0.85	2283
0.85-0.9	1006
0.9-0.95	118
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC233267
0.993	High Similarity	NPC105415
0.9861	High Similarity	NPC133856
0.9793	High Similarity	NPC273483
0.9718	High Similarity	NPC134621
0.966	High Similarity	NPC149618
0.966	High Similarity	NPC89625
0.965	High Similarity	NPC237208
0.965	High Similarity	NPC163846
0.965	High Similarity	NPC225173
0.9648	High Similarity	NPC66404
0.9648	High Similarity	NPC95123
0.9595	High Similarity	NPC146211
0.9583	High Similarity	NPC125801
0.958	High Similarity	NPC29577
0.9524	High Similarity	NPC217447
0.9517	High Similarity	NPC37139
0.9514	High Similarity	NPC473927
0.9507	High Similarity	NPC105648
0.9452	High Similarity	NPC97029
0.9452	High Similarity	NPC65589
0.9452	High Similarity	NPC97028
0.9452	High Similarity	NPC100985
0.9452	High Similarity	NPC158338
0.9452	High Similarity	NPC288036
0.9437	High Similarity	NPC220106
0.9404	High Similarity	NPC143050
0.9388	High Similarity	NPC150928
0.9388	High Similarity	NPC158866
0.9388	High Similarity	NPC60413
0.9384	High Similarity	NPC27221
0.9384	High Similarity	NPC7025
0.9384	High Similarity	NPC256672
0.9379	High Similarity	NPC267509
0.9371	High Similarity	NPC250755
0.9366	High Similarity	NPC165172
0.9329	High Similarity	NPC472799
0.9324	High Similarity	NPC474417
0.9324	High Similarity	NPC478148
0.9324	High Similarity	NPC72958
0.9324	High Similarity	NPC149526
0.9324	High Similarity	NPC232645
0.932	High Similarity	NPC6923
0.9315	High Similarity	NPC22005
0.9315	High Similarity	NPC7943
0.9315	High Similarity	NPC12305
0.9315	High Similarity	NPC123202
0.931	High Similarity	NPC32470
0.9306	High Similarity	NPC84266
0.9262	High Similarity	NPC175978
0.9262	High Similarity	NPC154683
0.9262	High Similarity	NPC40356
0.9262	High Similarity	NPC87708
0.9257	High Similarity	NPC474660
0.9257	High Similarity	NPC119929
0.9257	High Similarity	NPC309979
0.9257	High Similarity	NPC307780
0.9257	High Similarity	NPC325983
0.9252	High Similarity	NPC2569
0.9252	High Similarity	NPC172329
0.9236	High Similarity	NPC94076
0.9236	High Similarity	NPC182255
0.9221	High Similarity	NPC156082
0.9211	High Similarity	NPC474373
0.9205	High Similarity	NPC4547
0.92	High Similarity	NPC169990
0.92	High Similarity	NPC329844
0.92	High Similarity	NPC210942
0.9184	High Similarity	NPC34802
0.9178	High Similarity	NPC312789
0.9172	High Similarity	NPC159721
0.9172	High Similarity	NPC310340
0.9167	High Similarity	NPC67650
0.9167	High Similarity	NPC1704
0.9161	High Similarity	NPC112981
0.9145	High Similarity	NPC263483
0.9133	High Similarity	NPC271681
0.9128	High Similarity	NPC202595
0.9128	High Similarity	NPC473466
0.9116	High Similarity	NPC470322
0.9116	High Similarity	NPC154217
0.911	High Similarity	NPC151607
0.911	High Similarity	NPC189650
0.911	High Similarity	NPC42540
0.9103	High Similarity	NPC20216
0.9103	High Similarity	NPC30027
0.9097	High Similarity	NPC168471
0.9085	High Similarity	NPC158481
0.9079	High Similarity	NPC180924
0.9067	High Similarity	NPC227166
0.9067	High Similarity	NPC258249
0.906	High Similarity	NPC329933
0.906	High Similarity	NPC10027
0.906	High Similarity	NPC65775
0.9054	High Similarity	NPC190648
0.9054	High Similarity	NPC126767
0.9054	High Similarity	NPC142863
0.9054	High Similarity	NPC312929
0.9054	High Similarity	NPC118027
0.9054	High Similarity	NPC56433
0.9054	High Similarity	NPC289042
0.9054	High Similarity	NPC245584
0.9048	High Similarity	NPC75694
0.9048	High Similarity	NPC1886
0.9048	High Similarity	NPC196137
0.9045	High Similarity	NPC292788
0.9045	High Similarity	NPC272485
0.9041	High Similarity	NPC36181
0.9041	High Similarity	NPC471731
0.9041	High Similarity	NPC472006
0.9041	High Similarity	NPC469542
0.9041	High Similarity	NPC51106
0.9034	High Similarity	NPC275734
0.9026	High Similarity	NPC47623
0.9021	High Similarity	NPC194579
0.9021	High Similarity	NPC135837
0.902	High Similarity	NPC246647
0.902	High Similarity	NPC96342
0.902	High Similarity	NPC164110
0.902	High Similarity	NPC212967
0.9014	High Similarity	NPC180905
0.9014	High Similarity	NPC182496
0.9	High Similarity	NPC470107
0.9	High Similarity	NPC227122
0.9	High Similarity	NPC470568
0.9	High Similarity	NPC295036
0.9	High Similarity	NPC194379
0.8993	High Similarity	NPC471641
0.8993	High Similarity	NPC471642
0.8993	High Similarity	NPC240253
0.8993	High Similarity	NPC240622
0.8987	High Similarity	NPC49487
0.8987	High Similarity	NPC99613
0.8986	High Similarity	NPC187282
0.8986	High Similarity	NPC130176
0.8986	High Similarity	NPC290133
0.8986	High Similarity	NPC24136
0.8986	High Similarity	NPC181388
0.8986	High Similarity	NPC196114
0.8986	High Similarity	NPC99454
0.8981	High Similarity	NPC29160
0.898	High Similarity	NPC470296
0.898	High Similarity	NPC87609
0.898	High Similarity	NPC196459
0.898	High Similarity	NPC112791
0.898	High Similarity	NPC188632
0.898	High Similarity	NPC94794
0.8974	High Similarity	NPC474350
0.8973	High Similarity	NPC474385
0.8973	High Similarity	NPC49108
0.8973	High Similarity	NPC469579
0.8973	High Similarity	NPC471733
0.8966	High Similarity	NPC472601
0.8966	High Similarity	NPC472366
0.8966	High Similarity	NPC472600
0.8961	High Similarity	NPC85121
0.8954	High Similarity	NPC54928
0.8951	High Similarity	NPC118919
0.8951	High Similarity	NPC50455
0.8947	High Similarity	NPC477691
0.8947	High Similarity	NPC135522
0.8947	High Similarity	NPC214632
0.8947	High Similarity	NPC475895
0.894	High Similarity	NPC209142
0.894	High Similarity	NPC312549
0.894	High Similarity	NPC470569
0.8933	High Similarity	NPC269420
0.8933	High Similarity	NPC70764
0.8933	High Similarity	NPC476684
0.8931	High Similarity	NPC20543
0.8931	High Similarity	NPC109827
0.8931	High Similarity	NPC246716
0.8931	High Similarity	NPC124470
0.8931	High Similarity	NPC17219
0.8931	High Similarity	NPC239440
0.8926	High Similarity	NPC259632
0.8926	High Similarity	NPC137296
0.8926	High Similarity	NPC140120
0.8926	High Similarity	NPC8817
0.8924	High Similarity	NPC234331
0.8924	High Similarity	NPC76647
0.8919	High Similarity	NPC469935
0.8919	High Similarity	NPC271288
0.8919	High Similarity	NPC469953
0.8919	High Similarity	NPC473692
0.8919	High Similarity	NPC178627
0.891	High Similarity	NPC144843
0.8904	High Similarity	NPC472604
0.8904	High Similarity	NPC307990
0.8904	High Similarity	NPC241100
0.8904	High Similarity	NPC472603
0.8904	High Similarity	NPC37530
0.8904	High Similarity	NPC475730
0.8904	High Similarity	NPC472605
0.8904	High Similarity	NPC16455
0.8904	High Similarity	NPC159275
0.8903	High Similarity	NPC470810
0.8903	High Similarity	NPC186325
0.8897	High Similarity	NPC183639
0.8897	High Similarity	NPC199458

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 NPC291049 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	1016
0.2-0.3	1633
0.3-0.4	2612
0.4-0.5	1756
0.5-0.6	1137
0.6-0.7	442
0.7-0.8	160
0.8-0.85	39
0.85-0.9	15
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9073	High Similarity	NPD7819	Suspended
0.9048	High Similarity	NPD2533	Approved
0.9048	High Similarity	NPD2532	Approved
0.9048	High Similarity	NPD2534	Approved
0.9028	High Similarity	NPD970	Clinical (unspecified phase)
0.8792	High Similarity	NPD4378	Clinical (unspecified phase)
0.879	High Similarity	NPD6232	Discontinued
0.8726	High Similarity	NPD6959	Discontinued
0.8625	High Similarity	NPD7473	Discontinued
0.8581	High Similarity	NPD2393	Clinical (unspecified phase)
0.8571	High Similarity	NPD7411	Suspended
0.8562	High Similarity	NPD3226	Approved
0.8552	High Similarity	NPD1607	Approved
0.8535	High Similarity	NPD7075	Discontinued
0.8523	High Similarity	NPD3750	Approved
0.8519	High Similarity	NPD5844	Phase 1
0.8506	High Similarity	NPD6599	Discontinued
0.8503	High Similarity	NPD2935	Discontinued
0.8503	High Similarity	NPD1551	Phase 2
0.8471	Intermediate Similarity	NPD7768	Phase 2
0.8462	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD3749	Approved
0.8414	Intermediate Similarity	NPD1240	Approved
0.8408	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD1549	Phase 2
0.8355	Intermediate Similarity	NPD6799	Approved
0.8333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1243	Approved
0.8323	Intermediate Similarity	NPD5710	Approved
0.8323	Intermediate Similarity	NPD5711	Approved
0.8322	Intermediate Similarity	NPD2346	Discontinued
0.8311	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD1510	Phase 2
0.828	Intermediate Similarity	NPD1934	Approved
0.828	Intermediate Similarity	NPD6801	Discontinued
0.8278	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD2796	Approved
0.8235	Intermediate Similarity	NPD1511	Approved
0.8228	Intermediate Similarity	NPD2801	Approved
0.8212	Intermediate Similarity	NPD2800	Approved
0.8212	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD2799	Discontinued
0.8188	Intermediate Similarity	NPD3748	Approved
0.8176	Intermediate Similarity	NPD3817	Phase 2
0.8158	Intermediate Similarity	NPD4628	Phase 3
0.8153	Intermediate Similarity	NPD4380	Phase 2
0.8133	Intermediate Similarity	NPD6100	Approved
0.8133	Intermediate Similarity	NPD6099	Approved
0.8129	Intermediate Similarity	NPD1512	Approved
0.8125	Intermediate Similarity	NPD3882	Suspended
0.8125	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD7390	Discontinued
0.8113	Intermediate Similarity	NPD1465	Phase 2
0.8077	Intermediate Similarity	NPD920	Approved
0.8056	Intermediate Similarity	NPD1203	Approved
0.8052	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD6559	Discontinued
0.8013	Intermediate Similarity	NPD5405	Approved
0.8013	Intermediate Similarity	NPD5404	Approved
0.8013	Intermediate Similarity	NPD5408	Approved
0.8013	Intermediate Similarity	NPD5406	Approved
0.7976	Intermediate Similarity	NPD5953	Discontinued
0.7975	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD4625	Phase 3
0.7949	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6651	Approved
0.7914	Intermediate Similarity	NPD919	Approved
0.7905	Intermediate Similarity	NPD411	Approved
0.7892	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD6166	Phase 2
0.7891	Intermediate Similarity	NPD6832	Phase 2
0.7866	Intermediate Similarity	NPD5494	Approved
0.7862	Intermediate Similarity	NPD1283	Approved
0.7857	Intermediate Similarity	NPD7286	Phase 2
0.7857	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD1608	Approved
0.7847	Intermediate Similarity	NPD9717	Approved
0.7834	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD4308	Phase 3
0.7811	Intermediate Similarity	NPD7074	Phase 3
0.7808	Intermediate Similarity	NPD2797	Approved
0.7806	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD7003	Approved
0.7798	Intermediate Similarity	NPD3818	Discontinued
0.7785	Intermediate Similarity	NPD3268	Approved
0.7785	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2313	Discontinued
0.7778	Intermediate Similarity	NPD422	Phase 1
0.7771	Intermediate Similarity	NPD7229	Phase 3
0.7762	Intermediate Similarity	NPD4626	Approved
0.7751	Intermediate Similarity	NPD7054	Approved
0.7748	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD5403	Approved
0.773	Intermediate Similarity	NPD5402	Approved
0.7727	Intermediate Similarity	NPD2344	Approved
0.7727	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7472	Approved
0.7692	Intermediate Similarity	NPD7177	Discontinued
0.7682	Intermediate Similarity	NPD4060	Phase 1
0.7674	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD6273	Approved
0.7667	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6797	Phase 2
0.7655	Intermediate Similarity	NPD1281	Approved
0.7639	Intermediate Similarity	NPD17	Approved
0.7632	Intermediate Similarity	NPD447	Suspended
0.7632	Intermediate Similarity	NPD230	Phase 1
0.763	Intermediate Similarity	NPD8312	Approved
0.763	Intermediate Similarity	NPD8313	Approved
0.7622	Intermediate Similarity	NPD4288	Approved
0.7616	Intermediate Similarity	NPD7251	Discontinued
0.7614	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD5401	Approved
0.7607	Intermediate Similarity	NPD37	Approved
0.7605	Intermediate Similarity	NPD7199	Phase 2
0.7597	Intermediate Similarity	NPD7033	Discontinued
0.759	Intermediate Similarity	NPD6234	Discontinued
0.7576	Intermediate Similarity	NPD4966	Approved
0.7576	Intermediate Similarity	NPD4967	Phase 2
0.7576	Intermediate Similarity	NPD4965	Approved
0.7572	Intermediate Similarity	NPD7808	Phase 3
0.7569	Intermediate Similarity	NPD5691	Approved
0.7566	Intermediate Similarity	NPD943	Approved
0.7566	Intermediate Similarity	NPD4307	Phase 2
0.7566	Intermediate Similarity	NPD2979	Phase 3
0.7558	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4749	Approved
0.755	Intermediate Similarity	NPD3764	Approved
0.7548	Intermediate Similarity	NPD4477	Approved
0.7548	Intermediate Similarity	NPD4476	Approved
0.7534	Intermediate Similarity	NPD1201	Approved
0.7533	Intermediate Similarity	NPD4908	Phase 1
0.7532	Intermediate Similarity	NPD2309	Approved
0.7531	Intermediate Similarity	NPD7458	Discontinued
0.7516	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5124	Phase 1
0.7515	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD3225	Approved
0.745	Intermediate Similarity	NPD3267	Approved
0.745	Intermediate Similarity	NPD1470	Approved
0.745	Intermediate Similarity	NPD1164	Approved
0.745	Intermediate Similarity	NPD3266	Approved
0.7448	Intermediate Similarity	NPD1651	Approved
0.7439	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2438	Suspended
0.7434	Intermediate Similarity	NPD1296	Phase 2
0.7434	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4287	Approved
0.7415	Intermediate Similarity	NPD1611	Approved
0.7415	Intermediate Similarity	NPD1610	Phase 2
0.7407	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7783	Phase 2
0.74	Intermediate Similarity	NPD2798	Approved
0.7397	Intermediate Similarity	NPD1778	Approved
0.7396	Intermediate Similarity	NPD1247	Approved
0.7394	Intermediate Similarity	NPD8151	Discontinued
0.7389	Intermediate Similarity	NPD1471	Phase 3
0.7384	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD9545	Approved
0.7365	Intermediate Similarity	NPD3972	Approved
0.7361	Intermediate Similarity	NPD9493	Approved
0.7337	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2531	Phase 2
0.7312	Intermediate Similarity	NPD7435	Discontinued
0.7303	Intermediate Similarity	NPD8150	Discontinued
0.7296	Intermediate Similarity	NPD2654	Approved
0.729	Intermediate Similarity	NPD1933	Approved
0.729	Intermediate Similarity	NPD6355	Discontinued
0.7285	Intermediate Similarity	NPD1019	Discontinued
0.7285	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7228	Approved
0.7278	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8032	Phase 2
0.7268	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1548	Phase 1
0.7253	Intermediate Similarity	NPD4363	Phase 3
0.7253	Intermediate Similarity	NPD4360	Phase 2
0.7243	Intermediate Similarity	NPD6776	Approved
0.7243	Intermediate Similarity	NPD6782	Approved
0.7243	Intermediate Similarity	NPD6778	Approved
0.7243	Intermediate Similarity	NPD6780	Approved
0.7243	Intermediate Similarity	NPD6779	Approved
0.7243	Intermediate Similarity	NPD6777	Approved
0.7243	Intermediate Similarity	NPD6781	Approved
0.7237	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6971	Discontinued
0.7213	Intermediate Similarity	NPD4361	Phase 2
0.7213	Intermediate Similarity	NPD4362	Clinical (unspecified phase)

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