NPASS Compound

Structure

CID182421 OpenBabel06191715562D 21 23 0 0 1 0 0 0 0 0999 V2000 2.5981 -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 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 -1.7321 -0.0000 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 1.7321 -0.0000 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 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 -1.7321 -2.0000 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 0.8660 -0.5000 0.0000 C 0 0 1 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 1 8 1 0 0 0 0 2 7 1 0 0 0 0 2 9 2 0 0 0 0 3 8 2 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 4 11 1 0 0 0 0 5 10 1 0 0 0 0 5 14 2 0 0 0 0 6 12 1 0 0 0 0 6 13 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 12 20 2 0 0 0 0 13 7 1 6 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.06
Volume:	276.613
LogP:	2.124
LogD:	2.348
LogS:	-3.716
# Rotatable Bonds:	1
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.641
Synthetic Accessibility Score:	3.105
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.992
MDCK Permeability:	9.380873962072656e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.97
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	85.22016143798828%
Volume Distribution (VD):	0.761
Pgp-substrate:	14.99902629852295%

ADMET: Metabolism

CYP1A2-inhibitor:	0.932
CYP1A2-substrate:	0.222
CYP2C19-inhibitor:	0.309
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.644
CYP2C9-substrate:	0.938
CYP2D6-inhibitor:	0.708
CYP2D6-substrate:	0.533
CYP3A4-inhibitor:	0.904
CYP3A4-substrate:	0.119

ADMET: Excretion

Clearance (CL):	17.435
Half-life (T1/2):	0.87

ADMET: Toxicity

hERG Blockers:	0.147
Human Hepatotoxicity (H-HT):	0.186
Drug-inuced Liver Injury (DILI):	0.885
AMES Toxicity:	0.178
Rat Oral Acute Toxicity:	0.762
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.947
Carcinogencity:	0.301
Eye Corrosion:	0.028
Eye Irritation:	0.938
Respiratory Toxicity:	0.857

Download Data

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

Natural Product: NPC182421

Natural Product ID:	NPC182421
*Common Name:**	3',5,5',7-Tetrahydroxyflavanone
IUPAC Name:	(2S)-2-(3,5-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydrochromen-4-one
Synonyms:	3',5,5',7-Tetrahydroxyflavanone
Standard InCHIKey:	AYHOUUNTAVCXBN-ZDUSSCGKSA-N
Standard InCHI:	InChI=1S/C15H12O6/c16-8-1-7(2-9(17)3-8)13-6-12(20)15-11(19)4-10(18)5-14(15)21-13/h1-5,13,16-19H,6H2/t13-/m0/s1
SMILES:	c1c(cc(cc1O)O)[C@@H]1CC(=O)c2c(cc(cc2O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1272251
PubChem CID:	52945930
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] Flavanones

*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
NPO17675	Andira inermis	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11025148]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473438]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16203143]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16919944]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root bark	n.a.	n.a.	PMID[17608532]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950599]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19113968]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[19191562]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[19280148]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19285413]
NPO17675	Andira inermis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO20289	Dracocephalum tanguticum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19499937]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19660948]
NPO20289	Dracocephalum tanguticum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20932762]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23743282]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[25322455]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root barks	purchased from the local herbal market, Chungbuk, Korea	2012-JUL	PMID[26227773]
NPO40254	Opuntia humifusa	Species	Cactaceae	Eukaryota	Cladodes	n.a.	n.a.	PMID[32118424]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[8281582]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9525107]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17675	Andira inermis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22420	Lignum dalbergiae odoriferae rosewood	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17675	Andira inermis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26768	Lichtheimia blakesleeana	Species	Lichtheimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21187	Leucanthemopsis pallida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20289	Dracocephalum tanguticum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17675	Andira inermis	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
EC50	3
IC50	3
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	2
NON-MOLECULAR	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	IC50	=	81800.0	nM	PMID[564768]
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	Inhibition	=	53.6	%	PMID[564768]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	14000.0	nM	PMID[564769]
NPT1	Others	Radical scavenging activity		EC50	=	32150.0	nM	PMID[564765]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	161200000.0	nM	PMID[564765]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	16320.0	nM	PMID[564765]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[564767]

☑ 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 NPC182421 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	407
0.1-0.2	1780
0.2-0.3	4340
0.3-0.4	10636
0.4-0.5	7238
0.5-0.6	3604
0.6-0.7	5076
0.7-0.8	5407
0.8-0.85	2374
0.85-0.9	1432
0.9-0.95	382
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9853	High Similarity	NPC73028
0.964	High Similarity	NPC290133
0.964	High Similarity	NPC24136
0.964	High Similarity	NPC187282
0.963	High Similarity	NPC287246
0.963	High Similarity	NPC243083
0.963	High Similarity	NPC79943
0.963	High Similarity	NPC12296
0.963	High Similarity	NPC32441
0.963	High Similarity	NPC296490
0.963	High Similarity	NPC295261
0.963	High Similarity	NPC13768
0.963	High Similarity	NPC107586
0.9571	High Similarity	NPC21835
0.9559	High Similarity	NPC472460
0.9559	High Similarity	NPC329225
0.9559	High Similarity	NPC147686
0.9504	High Similarity	NPC294852
0.9504	High Similarity	NPC218569
0.9504	High Similarity	NPC188679
0.9504	High Similarity	NPC321011
0.9489	High Similarity	NPC310135
0.9489	High Similarity	NPC225153
0.9489	High Similarity	NPC316480
0.9489	High Similarity	NPC265871
0.9489	High Similarity	NPC20709
0.9489	High Similarity	NPC140890
0.9489	High Similarity	NPC274784
0.9489	High Similarity	NPC329203
0.9489	High Similarity	NPC222342
0.9489	High Similarity	NPC150648
0.9485	High Similarity	NPC84585
0.9485	High Similarity	NPC476480
0.9437	High Similarity	NPC183959
0.9437	High Similarity	NPC1612
0.9429	High Similarity	NPC470890
0.9424	High Similarity	NPC310340
0.9424	High Similarity	NPC169479
0.9424	High Similarity	NPC159855
0.942	High Similarity	NPC188243
0.942	High Similarity	NPC110228
0.942	High Similarity	NPC6407
0.942	High Similarity	NPC275734
0.9416	High Similarity	NPC118813
0.9412	High Similarity	NPC193792
0.9371	High Similarity	NPC338131
0.9371	High Similarity	NPC472633
0.9362	High Similarity	NPC472629
0.9357	High Similarity	NPC113770
0.9353	High Similarity	NPC96408
0.9353	High Similarity	NPC258630
0.9353	High Similarity	NPC4743
0.9353	High Similarity	NPC213322
0.9353	High Similarity	NPC156190
0.9353	High Similarity	NPC17170
0.9353	High Similarity	NPC279650
0.9353	High Similarity	NPC312391
0.9353	High Similarity	NPC166689
0.9353	High Similarity	NPC324386
0.9348	High Similarity	NPC261234
0.9343	High Similarity	NPC290291
0.9343	High Similarity	NPC275055
0.9343	High Similarity	NPC212767
0.9338	High Similarity	NPC9985
0.9338	High Similarity	NPC239495
0.9306	High Similarity	NPC204515
0.9291	High Similarity	NPC326506
0.9291	High Similarity	NPC142731
0.9291	High Similarity	NPC49130
0.9291	High Similarity	NPC279417
0.9291	High Similarity	NPC87486
0.9291	High Similarity	NPC124780
0.9291	High Similarity	NPC208176
0.9291	High Similarity	NPC469764
0.9291	High Similarity	NPC306607
0.9291	High Similarity	NPC62290
0.9291	High Similarity	NPC184649
0.9291	High Similarity	NPC311144
0.9291	High Similarity	NPC224714
0.9291	High Similarity	NPC303185
0.9291	High Similarity	NPC4152
0.9286	High Similarity	NPC32739
0.9286	High Similarity	NPC161506
0.9286	High Similarity	NPC306829
0.9286	High Similarity	NPC78
0.9286	High Similarity	NPC66515
0.9286	High Similarity	NPC166482
0.9286	High Similarity	NPC194432
0.9286	High Similarity	NPC220998
0.9286	High Similarity	NPC125855
0.9286	High Similarity	NPC182852
0.9286	High Similarity	NPC107572
0.9286	High Similarity	NPC167624
0.9286	High Similarity	NPC76372
0.9286	High Similarity	NPC202981
0.9286	High Similarity	NPC228504
0.9286	High Similarity	NPC148757
0.9286	High Similarity	NPC10937
0.9286	High Similarity	NPC64915
0.9286	High Similarity	NPC324134
0.9286	High Similarity	NPC227579
0.9286	High Similarity	NPC37496
0.9286	High Similarity	NPC324436
0.9286	High Similarity	NPC223500
0.9286	High Similarity	NPC328164
0.9286	High Similarity	NPC40833
0.9286	High Similarity	NPC166934
0.9286	High Similarity	NPC1089
0.9286	High Similarity	NPC265040
0.9286	High Similarity	NPC76338
0.9286	High Similarity	NPC177354
0.9286	High Similarity	NPC296917
0.9281	High Similarity	NPC284550
0.9281	High Similarity	NPC129853
0.9281	High Similarity	NPC76445
0.9275	High Similarity	NPC280284
0.9275	High Similarity	NPC188947
0.9275	High Similarity	NPC99333
0.9241	High Similarity	NPC106976
0.9241	High Similarity	NPC36835
0.9241	High Similarity	NPC260491
0.9241	High Similarity	NPC246162
0.9241	High Similarity	NPC9743
0.9241	High Similarity	NPC302950
0.9241	High Similarity	NPC19721
0.9241	High Similarity	NPC474843
0.9241	High Similarity	NPC61506
0.9241	High Similarity	NPC219582
0.9241	High Similarity	NPC236637
0.9241	High Similarity	NPC240476
0.9236	High Similarity	NPC202595
0.9236	High Similarity	NPC37348
0.9231	High Similarity	NPC3036
0.9231	High Similarity	NPC106328
0.9231	High Similarity	NPC35150
0.9225	High Similarity	NPC196114
0.9225	High Similarity	NPC1940
0.9225	High Similarity	NPC148011
0.9225	High Similarity	NPC299011
0.9225	High Similarity	NPC469758
0.922	High Similarity	NPC81697
0.922	High Similarity	NPC175504
0.922	High Similarity	NPC91560
0.922	High Similarity	NPC164980
0.922	High Similarity	NPC310130
0.922	High Similarity	NPC107177
0.922	High Similarity	NPC39329
0.922	High Similarity	NPC75049
0.922	High Similarity	NPC316816
0.922	High Similarity	NPC223812
0.922	High Similarity	NPC278249
0.922	High Similarity	NPC68104
0.922	High Similarity	NPC257097
0.922	High Similarity	NPC125894
0.922	High Similarity	NPC143896
0.922	High Similarity	NPC85162
0.922	High Similarity	NPC214166
0.922	High Similarity	NPC478086
0.922	High Similarity	NPC169591
0.922	High Similarity	NPC77794
0.922	High Similarity	NPC185276
0.922	High Similarity	NPC150408
0.922	High Similarity	NPC221432
0.922	High Similarity	NPC149026
0.9214	High Similarity	NPC248372
0.9214	High Similarity	NPC110038
0.9214	High Similarity	NPC3188
0.9197	High Similarity	NPC234560
0.9197	High Similarity	NPC39426
0.9191	High Similarity	NPC213216
0.9191	High Similarity	NPC78540
0.9191	High Similarity	NPC50898
0.9191	High Similarity	NPC274121
0.9178	High Similarity	NPC298692
0.9178	High Similarity	NPC246328
0.9178	High Similarity	NPC213896
0.9178	High Similarity	NPC18727
0.9178	High Similarity	NPC192083
0.9178	High Similarity	NPC325028
0.9178	High Similarity	NPC74924
0.9178	High Similarity	NPC256346
0.9178	High Similarity	NPC27532
0.9172	High Similarity	NPC232645
0.9172	High Similarity	NPC72958
0.9167	High Similarity	NPC105512
0.9167	High Similarity	NPC266499
0.9161	High Similarity	NPC40086
0.9161	High Similarity	NPC3779
0.9161	High Similarity	NPC211466
0.9161	High Similarity	NPC308200
0.9161	High Similarity	NPC476182
0.9161	High Similarity	NPC10990
0.9161	High Similarity	NPC473077
0.9161	High Similarity	NPC300988
0.9161	High Similarity	NPC176869
0.9161	High Similarity	NPC95864
0.9161	High Similarity	NPC122828
0.9161	High Similarity	NPC44721
0.9161	High Similarity	NPC296998
0.9155	High Similarity	NPC131568

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 NPC182421 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	403
0.1-0.2	948
0.2-0.3	1739
0.3-0.4	2576
0.4-0.5	1726
0.5-0.6	1119
0.6-0.7	446
0.7-0.8	129
0.8-0.85	38
0.85-0.9	21
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.963	High Similarity	NPD1552	Clinical (unspecified phase)
0.963	High Similarity	NPD1550	Clinical (unspecified phase)
0.9559	High Similarity	NPD1549	Phase 2
0.9241	High Similarity	NPD1934	Approved
0.9197	High Similarity	NPD1510	Phase 2
0.9178	High Similarity	NPD2393	Clinical (unspecified phase)
0.9085	High Similarity	NPD1511	Approved
0.9021	High Similarity	NPD4378	Clinical (unspecified phase)
0.8958	High Similarity	NPD1512	Approved
0.8905	High Similarity	NPD1240	Approved
0.8857	High Similarity	NPD2796	Approved
0.8844	High Similarity	NPD4380	Phase 2
0.8777	High Similarity	NPD1607	Approved
0.8742	High Similarity	NPD4381	Clinical (unspecified phase)
0.8733	High Similarity	NPD8443	Clinical (unspecified phase)
0.8693	High Similarity	NPD6959	Discontinued
0.8667	High Similarity	NPD7819	Suspended
0.8667	High Similarity	NPD2801	Approved
0.8645	High Similarity	NPD6166	Phase 2
0.8645	High Similarity	NPD6168	Clinical (unspecified phase)
0.8645	High Similarity	NPD6167	Clinical (unspecified phase)
0.8618	High Similarity	NPD7075	Discontinued
0.8601	High Similarity	NPD970	Clinical (unspecified phase)
0.8553	High Similarity	NPD4868	Clinical (unspecified phase)
0.8543	High Similarity	NPD7096	Clinical (unspecified phase)
0.8533	High Similarity	NPD7411	Suspended
0.8503	High Similarity	NPD7410	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD1551	Phase 2
0.8431	Intermediate Similarity	NPD3882	Suspended
0.8428	Intermediate Similarity	NPD7074	Phase 3
0.8418	Intermediate Similarity	NPD3818	Discontinued
0.8366	Intermediate Similarity	NPD3817	Phase 2
0.8365	Intermediate Similarity	NPD7054	Approved
0.8356	Intermediate Similarity	NPD3750	Approved
0.8313	Intermediate Similarity	NPD7472	Approved
0.8311	Intermediate Similarity	NPD6799	Approved
0.8288	Intermediate Similarity	NPD2800	Approved
0.8269	Intermediate Similarity	NPD5494	Approved
0.8261	Intermediate Similarity	NPD6797	Phase 2
0.8258	Intermediate Similarity	NPD3749	Approved
0.825	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD6801	Discontinued
0.8235	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD7251	Discontinued
0.8176	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD7808	Phase 3
0.816	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD2534	Approved
0.8133	Intermediate Similarity	NPD2533	Approved
0.8133	Intermediate Similarity	NPD2532	Approved
0.8129	Intermediate Similarity	NPD5402	Approved
0.8112	Intermediate Similarity	NPD943	Approved
0.8112	Intermediate Similarity	NPD1613	Approved
0.8112	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD6599	Discontinued
0.8102	Intermediate Similarity	NPD1610	Phase 2
0.8099	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD6559	Discontinued
0.8082	Intermediate Similarity	NPD6100	Approved
0.8082	Intermediate Similarity	NPD2935	Discontinued
0.8082	Intermediate Similarity	NPD6099	Approved
0.8077	Intermediate Similarity	NPD7768	Phase 2
0.8065	Intermediate Similarity	NPD1465	Phase 2
0.8041	Intermediate Similarity	NPD1243	Approved
0.8041	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD920	Approved
0.8026	Intermediate Similarity	NPD5403	Approved
0.8014	Intermediate Similarity	NPD3748	Approved
0.8014	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD5401	Approved
0.8013	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1203	Approved
0.8	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD1548	Phase 1
0.7937	Intermediate Similarity	NPD6232	Discontinued
0.7914	Intermediate Similarity	NPD5844	Phase 1
0.7905	Intermediate Similarity	NPD2344	Approved
0.7901	Intermediate Similarity	NPD7473	Discontinued
0.7877	Intermediate Similarity	NPD6651	Approved
0.7867	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD2313	Discontinued
0.7832	Intermediate Similarity	NPD4908	Phase 1
0.7808	Intermediate Similarity	NPD230	Phase 1
0.7806	Intermediate Similarity	NPD3226	Approved
0.7785	Intermediate Similarity	NPD2346	Discontinued
0.7778	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD1247	Approved
0.775	Intermediate Similarity	NPD919	Approved
0.7748	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD4628	Phase 3
0.7725	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD7390	Discontinued
0.7711	Intermediate Similarity	NPD5953	Discontinued
0.7697	Intermediate Similarity	NPD7286	Phase 2
0.7697	Intermediate Similarity	NPD2309	Approved
0.7687	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD1608	Approved
0.766	Intermediate Similarity	NPD9717	Approved
0.7651	Intermediate Similarity	NPD2799	Discontinued
0.7651	Intermediate Similarity	NPD7033	Discontinued
0.7639	Intermediate Similarity	NPD2861	Phase 2
0.7636	Intermediate Similarity	NPD3751	Discontinued
0.7607	Intermediate Similarity	NPD5710	Approved
0.7607	Intermediate Similarity	NPD5711	Approved
0.7589	Intermediate Similarity	NPD422	Phase 1
0.7589	Intermediate Similarity	NPD1201	Approved
0.7586	Intermediate Similarity	NPD4360	Phase 2
0.7586	Intermediate Similarity	NPD6832	Phase 2
0.7586	Intermediate Similarity	NPD4363	Phase 3
0.7568	Intermediate Similarity	NPD447	Suspended
0.7561	Intermediate Similarity	NPD3926	Phase 2
0.7533	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1470	Approved
0.75	Intermediate Similarity	NPD3787	Discontinued
0.7484	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4749	Approved
0.7483	Intermediate Similarity	NPD411	Approved
0.7483	Intermediate Similarity	NPD3268	Approved
0.7468	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2654	Approved
0.7448	Intermediate Similarity	NPD2798	Approved
0.7447	Intermediate Similarity	NPD17	Approved
0.7438	Intermediate Similarity	NPD6844	Discontinued
0.7431	Intermediate Similarity	NPD3225	Approved
0.7429	Intermediate Similarity	NPD9545	Approved
0.7417	Intermediate Similarity	NPD4308	Phase 3
0.7415	Intermediate Similarity	NPD3027	Phase 3
0.7415	Intermediate Similarity	NPD4625	Phase 3
0.7379	Intermediate Similarity	NPD2797	Approved
0.7371	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8312	Approved
0.7368	Intermediate Similarity	NPD8313	Approved
0.7365	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1296	Phase 2
0.7346	Intermediate Similarity	NPD4288	Approved
0.7333	Intermediate Similarity	NPD1933	Approved
0.7333	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5124	Phase 1
0.7329	Intermediate Similarity	NPD1019	Discontinued
0.7319	Intermediate Similarity	NPD1241	Discontinued
0.7296	Intermediate Similarity	NPD1653	Approved
0.7292	Intermediate Similarity	NPD1481	Phase 2
0.7289	Intermediate Similarity	NPD7229	Phase 3
0.7286	Intermediate Similarity	NPD9493	Approved
0.7278	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3267	Approved
0.726	Intermediate Similarity	NPD3266	Approved
0.7257	Intermediate Similarity	NPD4287	Approved
0.7248	Intermediate Similarity	NPD3764	Approved
0.7248	Intermediate Similarity	NPD6798	Discontinued
0.7247	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD4361	Phase 2
0.7235	Intermediate Similarity	NPD1729	Discontinued
0.7229	Intermediate Similarity	NPD7199	Phase 2
0.7226	Intermediate Similarity	NPD1652	Phase 2
0.7222	Intermediate Similarity	NPD37	Approved
0.7222	Intermediate Similarity	NPD1535	Discovery
0.7212	Intermediate Similarity	NPD6234	Discontinued
0.7208	Intermediate Similarity	NPD1471	Phase 3
0.7207	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4966	Approved
0.7195	Intermediate Similarity	NPD4965	Approved
0.7195	Intermediate Similarity	NPD4967	Phase 2
0.7172	Intermediate Similarity	NPD3972	Approved
0.7172	Intermediate Similarity	NPD9269	Phase 2
0.7162	Intermediate Similarity	NPD9494	Approved
0.7152	Intermediate Similarity	NPD4307	Phase 2
0.7151	Intermediate Similarity	NPD6104	Discontinued
0.7143	Intermediate Similarity	NPD5406	Approved
0.7143	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5408	Approved
0.7143	Intermediate Similarity	NPD1164	Approved
0.7143	Intermediate Similarity	NPD5405	Approved
0.7143	Intermediate Similarity	NPD5404	Approved
0.7135	Intermediate Similarity	NPD7584	Approved
0.7134	Intermediate Similarity	NPD2296	Approved
0.7134	Intermediate Similarity	NPD6190	Approved
0.7133	Intermediate Similarity	NPD9268	Approved
0.7105	Intermediate Similarity	NPD6355	Discontinued
0.7101	Intermediate Similarity	NPD2403	Approved
0.7097	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD6780	Approved
0.7088	Intermediate Similarity	NPD6776	Approved
0.7088	Intermediate Similarity	NPD6781	Approved
0.7088	Intermediate Similarity	NPD6778	Approved
0.7088	Intermediate Similarity	NPD6777	Approved
0.7088	Intermediate Similarity	NPD6782	Approved
0.7088	Intermediate Similarity	NPD6779	Approved
0.7086	Intermediate Similarity	NPD6233	Phase 2
0.7083	Intermediate Similarity	NPD1778	Approved
0.7073	Intermediate Similarity	NPD5761	Phase 2
0.7073	Intermediate Similarity	NPD5760	Phase 2
0.7073	Intermediate Similarity	NPD8455	Phase 2
0.7063	Intermediate Similarity	NPD6273	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