NPASS Compound

Structure

CID308200 OpenBabel06191716112D 31 33 0 0 1 0 0 0 0 0999 V2000 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 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 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 2.5981 2.5000 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 2.5981 -0.5000 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 -1.7321 -2.0000 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 4.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 3 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 -2.5981 -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 1.7321 1.0000 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 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 7 1 0 0 0 0 5 13 2 0 0 0 0 6 8 1 0 0 0 0 6 14 2 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 10 19 1 0 0 0 0 11 20 2 0 0 0 0 11 21 1 0 0 0 0 12 18 1 0 0 0 0 12 31 1 0 0 0 0 15 18 1 0 0 0 0 15 23 2 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 17 20 1 0 0 0 0 17 24 2 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 21 22 2 0 0 0 0 21 31 1 0 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 25 30 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.19
Volume:	444.3
LogP:	6.12
LogD:	3.08
LogS:	-3.564
# Rotatable Bonds:	5
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.509
Synthetic Accessibility Score:	3.737
Fsp3:	0.32
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.998
MDCK Permeability:	1.103747035813285e-05
Pgp-inhibitor:	0.719
Pgp-substrate:	0.365
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	98.7573013305664%
Volume Distribution (VD):	1.329
Pgp-substrate:	2.4292078018188477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.516
CYP1A2-substrate:	0.489
CYP2C19-inhibitor:	0.861
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.866
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.833
CYP2D6-substrate:	0.384
CYP3A4-inhibitor:	0.215
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	14.015
Half-life (T1/2):	0.113

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.721
Drug-inuced Liver Injury (DILI):	0.595
AMES Toxicity:	0.048
Rat Oral Acute Toxicity:	0.44
Maximum Recommended Daily Dose:	0.083
Skin Sensitization:	0.941
Carcinogencity:	0.061
Eye Corrosion:	0.003
Eye Irritation:	0.783
Respiratory Toxicity:	0.1

Download Data

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

Natural Product: NPC308200

Natural Product ID:	NPC308200
*Common Name:**	3-(2,4-Dihydroxy-3-(3-Methylbut-2-Enyl)Phenyl)-5,7-Dihydroxy-6-(3-Methylbut-2-Enyl)Chroman-4-One
IUPAC Name:	3-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	RIWDYFGEQJAMKI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H28O6/c1-13(2)5-7-16-19(26)10-9-15(23(16)28)18-12-31-21-11-20(27)17(8-6-14(3)4)24(29)22(21)25(18)30/h5-6,9-11,18,26-29H,7-8,12H2,1-4H3
SMILES:	CC(=CCc1c(O)cc2c(c1O)C(=O)C(CO2)c1ccc(c(c1O)CC=C(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3746555
PubChem CID:	480786
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003525] 3'-prenylated isoflavanones

*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
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11524125]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11524125]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28522265]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29641206]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	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	2
Others	3

Activity Type	# Activity
Cell Line	1
Individual Protein	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	>	200000.0	nM	PMID[528733]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	>	60.0	%	PMID[528734]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	80.0	%	PMID[528734]
NPT2	Others	Unspecified		Inhibition	>	40.0	%	PMID[528734]

☑ 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 NPC308200 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	372
0.1-0.2	1447
0.2-0.3	3452
0.3-0.4	8603
0.4-0.5	10016
0.5-0.6	3509
0.6-0.7	5215
0.7-0.8	5448
0.8-0.85	2353
0.85-0.9	1502
0.9-0.95	682
0.95-1	98

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC39195
0.9929	High Similarity	NPC145467
0.9859	High Similarity	NPC471114
0.9857	High Similarity	NPC271288
0.9857	High Similarity	NPC311144
0.979	High Similarity	NPC471115
0.979	High Similarity	NPC29777
0.9787	High Similarity	NPC299011
0.9786	High Similarity	NPC113770
0.9716	High Similarity	NPC303185
0.9716	High Similarity	NPC184649
0.9648	High Similarity	NPC477955
0.9648	High Similarity	NPC472629
0.9645	High Similarity	NPC107177
0.9645	High Similarity	NPC223812
0.9645	High Similarity	NPC85162
0.9645	High Similarity	NPC77794
0.9645	High Similarity	NPC81697
0.9645	High Similarity	NPC125894
0.9645	High Similarity	NPC278249
0.9583	High Similarity	NPC473016
0.958	High Similarity	NPC300988
0.958	High Similarity	NPC10990
0.9577	High Similarity	NPC235217
0.9577	High Similarity	NPC131568
0.9577	High Similarity	NPC473013
0.9577	High Similarity	NPC124780
0.9577	High Similarity	NPC473015
0.9577	High Similarity	NPC470890
0.9577	High Similarity	NPC131579
0.9577	High Similarity	NPC473014
0.9577	High Similarity	NPC87486
0.9574	High Similarity	NPC177354
0.9574	High Similarity	NPC64915
0.9574	High Similarity	NPC167624
0.9574	High Similarity	NPC324436
0.9574	High Similarity	NPC220998
0.9574	High Similarity	NPC76338
0.9574	High Similarity	NPC202981
0.9574	High Similarity	NPC66515
0.9574	High Similarity	NPC10937
0.9574	High Similarity	NPC40833
0.9574	High Similarity	NPC76372
0.9574	High Similarity	NPC328164
0.9574	High Similarity	NPC324134
0.9574	High Similarity	NPC148757
0.9574	High Similarity	NPC125855
0.9574	High Similarity	NPC37496
0.9574	High Similarity	NPC296917
0.9574	High Similarity	NPC1089
0.9574	High Similarity	NPC194432
0.9574	High Similarity	NPC306829
0.9574	High Similarity	NPC182852
0.9574	High Similarity	NPC166934
0.9574	High Similarity	NPC161506
0.9574	High Similarity	NPC32739
0.9574	High Similarity	NPC265040
0.9574	High Similarity	NPC166482
0.9574	High Similarity	NPC107572
0.9574	High Similarity	NPC227579
0.9574	High Similarity	NPC228504
0.9574	High Similarity	NPC78
0.9574	High Similarity	NPC223500
0.9571	High Similarity	NPC129853
0.9571	High Similarity	NPC284550
0.9571	High Similarity	NPC76445
0.9521	High Similarity	NPC210597
0.951	High Similarity	NPC24136
0.951	High Similarity	NPC187282
0.951	High Similarity	NPC127059
0.951	High Similarity	NPC290133
0.951	High Similarity	NPC285630
0.9507	High Similarity	NPC164980
0.9507	High Similarity	NPC221432
0.9507	High Similarity	NPC91560
0.9507	High Similarity	NPC316816
0.9507	High Similarity	NPC39329
0.9507	High Similarity	NPC478086
0.9507	High Similarity	NPC185276
0.9507	High Similarity	NPC75049
0.9507	High Similarity	NPC18585
0.9507	High Similarity	NPC149026
0.9507	High Similarity	NPC106985
0.9507	High Similarity	NPC169591
0.9507	High Similarity	NPC68104
0.9507	High Similarity	NPC214166
0.9507	High Similarity	NPC166138
0.9507	High Similarity	NPC310130
0.9507	High Similarity	NPC257097
0.9507	High Similarity	NPC175504
0.9507	High Similarity	NPC150408
0.9507	High Similarity	NPC143896
0.9504	High Similarity	NPC166689
0.9504	High Similarity	NPC3188
0.9504	High Similarity	NPC282300
0.9504	High Similarity	NPC110038
0.9504	High Similarity	NPC213322
0.9504	High Similarity	NPC258630
0.9504	High Similarity	NPC96408
0.9504	High Similarity	NPC17170
0.9504	High Similarity	NPC156190
0.9504	High Similarity	NPC4743
0.9504	High Similarity	NPC312391
0.9504	High Similarity	NPC324386
0.9504	High Similarity	NPC279650
0.9504	High Similarity	NPC248372
0.95	High Similarity	NPC316480
0.9456	High Similarity	NPC100134
0.9456	High Similarity	NPC1477
0.9456	High Similarity	NPC209760
0.9456	High Similarity	NPC213608
0.9452	High Similarity	NPC178484
0.9448	High Similarity	NPC470461
0.9448	High Similarity	NPC266499
0.9448	High Similarity	NPC317492
0.9444	High Similarity	NPC473077
0.9444	High Similarity	NPC296998
0.9441	High Similarity	NPC273538
0.9441	High Similarity	NPC234629
0.9441	High Similarity	NPC197252
0.9441	High Similarity	NPC236766
0.9441	High Similarity	NPC311741
0.9441	High Similarity	NPC326500
0.9441	High Similarity	NPC209040
0.9441	High Similarity	NPC216538
0.9441	High Similarity	NPC224714
0.9437	High Similarity	NPC144499
0.9433	High Similarity	NPC188243
0.9433	High Similarity	NPC159275
0.9433	High Similarity	NPC110228
0.9433	High Similarity	NPC241100
0.9433	High Similarity	NPC69769
0.9433	High Similarity	NPC6407
0.9429	High Similarity	NPC118813
0.9392	High Similarity	NPC476169
0.9392	High Similarity	NPC471116
0.9388	High Similarity	NPC216035
0.9388	High Similarity	NPC5871
0.9388	High Similarity	NPC217149
0.9384	High Similarity	NPC472633
0.9384	High Similarity	NPC227122
0.9384	High Similarity	NPC476185
0.9384	High Similarity	NPC321896
0.9379	High Similarity	NPC470460
0.9379	High Similarity	NPC266572
0.9379	High Similarity	NPC168085
0.9379	High Similarity	NPC37135
0.9379	High Similarity	NPC296869
0.9379	High Similarity	NPC186397
0.9375	High Similarity	NPC470131
0.9375	High Similarity	NPC312973
0.9375	High Similarity	NPC88964
0.9375	High Similarity	NPC470647
0.9375	High Similarity	NPC470134
0.9375	High Similarity	NPC178343
0.9375	High Similarity	NPC54577
0.9375	High Similarity	NPC474161
0.9375	High Similarity	NPC475052
0.9375	High Similarity	NPC83357
0.9375	High Similarity	NPC473078
0.9375	High Similarity	NPC20488
0.9375	High Similarity	NPC67805
0.9375	High Similarity	NPC109183
0.9375	High Similarity	NPC301276
0.9375	High Similarity	NPC124729
0.9375	High Similarity	NPC476088
0.9375	High Similarity	NPC470132
0.9375	High Similarity	NPC111786
0.9375	High Similarity	NPC142405
0.9375	High Similarity	NPC246948
0.9375	High Similarity	NPC195621
0.9375	High Similarity	NPC470133
0.9375	High Similarity	NPC5820
0.9375	High Similarity	NPC267375
0.9375	High Similarity	NPC176229
0.9375	High Similarity	NPC214774
0.9375	High Similarity	NPC306488
0.9371	High Similarity	NPC212932
0.9371	High Similarity	NPC11700
0.9371	High Similarity	NPC190637
0.9371	High Similarity	NPC24821
0.9371	High Similarity	NPC9117
0.9371	High Similarity	NPC293053
0.9371	High Similarity	NPC219915
0.9366	High Similarity	NPC268204
0.9366	High Similarity	NPC52789
0.9366	High Similarity	NPC469404
0.9366	High Similarity	NPC26051
0.9366	High Similarity	NPC110969
0.9366	High Similarity	NPC55832
0.9362	High Similarity	NPC96565
0.9362	High Similarity	NPC261234
0.9362	High Similarity	NPC222342
0.9362	High Similarity	NPC150648
0.9362	High Similarity	NPC225153
0.9362	High Similarity	NPC78913
0.9362	High Similarity	NPC301217
0.9362	High Similarity	NPC220062
0.9362	High Similarity	NPC216978
0.9362	High Similarity	NPC303633

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 NPC308200 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	912
0.2-0.3	1488
0.3-0.4	2510
0.4-0.5	1981
0.5-0.6	1163
0.6-0.7	514
0.7-0.8	171
0.8-0.85	45
0.85-0.9	18
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9441	High Similarity	NPD4378	Clinical (unspecified phase)
0.9262	High Similarity	NPD8443	Clinical (unspecified phase)
0.922	High Similarity	NPD1550	Clinical (unspecified phase)
0.922	High Similarity	NPD1552	Clinical (unspecified phase)
0.9195	High Similarity	NPD2393	Clinical (unspecified phase)
0.9155	High Similarity	NPD1549	Phase 2
0.8993	High Similarity	NPD4380	Phase 2
0.8944	High Similarity	NPD1510	Phase 2
0.894	High Similarity	NPD7819	Suspended
0.8933	High Similarity	NPD7411	Suspended
0.8912	High Similarity	NPD7410	Clinical (unspecified phase)
0.8889	High Similarity	NPD7075	Discontinued
0.8881	High Similarity	NPD2796	Approved
0.8874	High Similarity	NPD1934	Approved
0.8816	High Similarity	NPD7096	Clinical (unspecified phase)
0.8794	High Similarity	NPD1240	Approved
0.8718	High Similarity	NPD6959	Discontinued
0.8699	High Similarity	NPD2800	Approved
0.8693	High Similarity	NPD2801	Approved
0.8671	High Similarity	NPD1607	Approved
0.8671	High Similarity	NPD7852	Clinical (unspecified phase)
0.8654	High Similarity	NPD5494	Approved
0.8645	High Similarity	NPD4381	Clinical (unspecified phase)
0.8591	High Similarity	NPD1511	Approved
0.8581	High Similarity	NPD7768	Phase 2
0.8509	High Similarity	NPD7804	Clinical (unspecified phase)
0.8506	High Similarity	NPD6801	Discontinued
0.8477	Intermediate Similarity	NPD1512	Approved
0.8467	Intermediate Similarity	NPD6799	Approved
0.8462	Intermediate Similarity	NPD3882	Suspended
0.8446	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD6166	Phase 2
0.8438	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD2799	Discontinued
0.8411	Intermediate Similarity	NPD2534	Approved
0.8411	Intermediate Similarity	NPD2532	Approved
0.8411	Intermediate Similarity	NPD2533	Approved
0.8408	Intermediate Similarity	NPD3749	Approved
0.8392	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD3750	Approved
0.8385	Intermediate Similarity	NPD7473	Discontinued
0.8378	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD6599	Discontinued
0.8313	Intermediate Similarity	NPD6232	Discontinued
0.8303	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD920	Approved
0.8288	Intermediate Similarity	NPD6651	Approved
0.828	Intermediate Similarity	NPD3817	Phase 2
0.8264	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD4908	Phase 1
0.8243	Intermediate Similarity	NPD1551	Phase 2
0.8243	Intermediate Similarity	NPD2935	Discontinued
0.8232	Intermediate Similarity	NPD7074	Phase 3
0.8228	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD3818	Discontinued
0.8188	Intermediate Similarity	NPD2344	Approved
0.8182	Intermediate Similarity	NPD5953	Discontinued
0.8171	Intermediate Similarity	NPD7054	Approved
0.8171	Intermediate Similarity	NPD7286	Phase 2
0.817	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD1610	Phase 2
0.8138	Intermediate Similarity	NPD2313	Discontinued
0.8133	Intermediate Similarity	NPD6559	Discontinued
0.8121	Intermediate Similarity	NPD6099	Approved
0.8121	Intermediate Similarity	NPD6100	Approved
0.8121	Intermediate Similarity	NPD7472	Approved
0.8079	Intermediate Similarity	NPD1243	Approved
0.8077	Intermediate Similarity	NPD3226	Approved
0.8072	Intermediate Similarity	NPD6797	Phase 2
0.8067	Intermediate Similarity	NPD2346	Discontinued
0.8061	Intermediate Similarity	NPD5844	Phase 1
0.8054	Intermediate Similarity	NPD3748	Approved
0.8054	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD4360	Phase 2
0.8035	Intermediate Similarity	NPD4363	Phase 3
0.8026	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7251	Discontinued
0.7976	Intermediate Similarity	NPD7808	Phase 3
0.7976	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD2309	Approved
0.7949	Intermediate Similarity	NPD5403	Approved
0.7937	Intermediate Similarity	NPD5402	Approved
0.7908	Intermediate Similarity	NPD4628	Phase 3
0.7908	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD3268	Approved
0.7887	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD7390	Discontinued
0.7866	Intermediate Similarity	NPD5711	Approved
0.7866	Intermediate Similarity	NPD5710	Approved
0.7862	Intermediate Similarity	NPD2798	Approved
0.7821	Intermediate Similarity	NPD5401	Approved
0.7805	Intermediate Similarity	NPD1247	Approved
0.7793	Intermediate Similarity	NPD2797	Approved
0.7793	Intermediate Similarity	NPD1203	Approved
0.7785	Intermediate Similarity	NPD943	Approved
0.7784	Intermediate Similarity	NPD4361	Phase 2
0.7784	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD1465	Phase 2
0.7758	Intermediate Similarity	NPD7229	Phase 3
0.7755	Intermediate Similarity	NPD6832	Phase 2
0.7751	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5124	Phase 1
0.7733	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1548	Phase 1
0.7712	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD3926	Phase 2
0.7707	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD4625	Phase 3
0.7697	Intermediate Similarity	NPD7033	Discontinued
0.7683	Intermediate Similarity	NPD919	Approved
0.7625	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7458	Discontinued
0.7616	Intermediate Similarity	NPD8312	Approved
0.7616	Intermediate Similarity	NPD8313	Approved
0.7614	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1608	Approved
0.7586	Intermediate Similarity	NPD9717	Approved
0.7568	Intermediate Similarity	NPD2861	Phase 2
0.7551	Intermediate Similarity	NPD3266	Approved
0.7551	Intermediate Similarity	NPD3267	Approved
0.755	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1613	Approved
0.7534	Intermediate Similarity	NPD4749	Approved
0.7533	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD422	Phase 1
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD2654	Approved
0.7485	Intermediate Similarity	NPD1729	Discontinued
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.7468	Intermediate Similarity	NPD4308	Phase 3
0.7466	Intermediate Similarity	NPD3972	Approved
0.7456	Intermediate Similarity	NPD2403	Approved
0.7452	Intermediate Similarity	NPD7003	Approved
0.745	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3787	Discontinued
0.7439	Intermediate Similarity	NPD5760	Phase 2
0.7439	Intermediate Similarity	NPD5761	Phase 2
0.7436	Intermediate Similarity	NPD2424	Discontinued
0.7432	Intermediate Similarity	NPD1470	Approved
0.7417	Intermediate Similarity	NPD3764	Approved
0.7401	Intermediate Similarity	NPD4287	Approved
0.7397	Intermediate Similarity	NPD1201	Approved
0.7394	Intermediate Similarity	NPD2296	Approved
0.7394	Intermediate Similarity	NPD4288	Approved
0.7391	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1933	Approved
0.7386	Intermediate Similarity	NPD8434	Phase 2
0.7386	Intermediate Similarity	NPD447	Suspended
0.7386	Intermediate Similarity	NPD6355	Discontinued
0.7381	Intermediate Similarity	NPD7199	Phase 2
0.7379	Intermediate Similarity	NPD17	Approved
0.7378	Intermediate Similarity	NPD6844	Discontinued
0.7378	Intermediate Similarity	NPD37	Approved
0.7372	Intermediate Similarity	NPD6005	Phase 3
0.7372	Intermediate Similarity	NPD1471	Phase 3
0.7372	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6004	Phase 3
0.7372	Intermediate Similarity	NPD6002	Phase 3
0.7372	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7584	Approved
0.7365	Intermediate Similarity	NPD6234	Discontinued
0.7365	Intermediate Similarity	NPD3225	Approved
0.7361	Intermediate Similarity	NPD9545	Approved
0.7355	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4965	Approved
0.7349	Intermediate Similarity	NPD4967	Phase 2
0.7349	Intermediate Similarity	NPD4966	Approved
0.7333	Intermediate Similarity	NPD8455	Phase 2
0.7322	Intermediate Similarity	NPD6777	Approved
0.7322	Intermediate Similarity	NPD6779	Approved
0.7322	Intermediate Similarity	NPD6780	Approved
0.7322	Intermediate Similarity	NPD6781	Approved
0.7322	Intermediate Similarity	NPD6778	Approved
0.7322	Intermediate Similarity	NPD6782	Approved
0.7322	Intermediate Similarity	NPD6776	Approved
0.732	Intermediate Similarity	NPD4060	Phase 1
0.7317	Intermediate Similarity	NPD5889	Approved
0.7317	Intermediate Similarity	NPD5890	Approved
0.7315	Intermediate Similarity	NPD1164	Approved
0.7308	Intermediate Similarity	NPD5405	Approved
0.7308	Intermediate Similarity	NPD5404	Approved
0.7308	Intermediate Similarity	NPD5406	Approved
0.7308	Intermediate Similarity	NPD5408	Approved
0.7308	Intermediate Similarity	NPD4476	Approved
0.7308	Intermediate Similarity	NPD4477	Approved
0.7303	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6798	Discontinued
0.7299	Intermediate Similarity	NPD6104	Discontinued
0.7294	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD8150	Discontinued
0.7273	Intermediate Similarity	NPD7577	Discontinued
0.7273	Intermediate Similarity	NPD6280	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