NPASS Compound

Structure

NPC214236 OpenBabel07101719122D 30 33 0 0 0 0 0 0 0 0999 V2000 1.7321 -3.0000 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 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -0.3660 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 6.0622 0.5000 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 6.9282 -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 -1.0000 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 1.5000 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 2.5981 -2.5000 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 6.9282 -1.0000 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 2.0000 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 1.5000 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 0.8660 0.5000 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 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 3.4641 -0.0000 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 10 1 0 0 0 0 5 14 2 0 0 0 0 6 8 1 0 0 0 0 6 15 2 0 0 0 0 7 9 2 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 12 2 0 0 0 0 11 17 1 0 0 0 0 12 25 1 0 0 0 0 13 19 1 0 0 0 0 13 20 2 0 0 0 0 15 20 1 0 0 0 0 16 26 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 21 1 0 0 0 0 19 27 2 0 0 0 0 20 29 1 0 0 0 0 21 22 1 0 0 0 0 21 24 2 0 0 0 0 22 28 1 0 0 0 0 23 30 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.16
Volume:	424.317
LogP:	6.696
LogD:	4.189
LogS:	-2.419
# Rotatable Bonds:	3
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.558
Synthetic Accessibility Score:	3.109
Fsp3:	0.24
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:	-4.726
MDCK Permeability:	1.4843488315818831e-05
Pgp-inhibitor:	0.895
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.062
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.181

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	96.77066040039062%
Volume Distribution (VD):	0.67
Pgp-substrate:	5.4003586769104%

ADMET: Metabolism

CYP1A2-inhibitor:	0.758
CYP1A2-substrate:	0.165
CYP2C19-inhibitor:	0.928
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.896
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.702
CYP2D6-substrate:	0.279
CYP3A4-inhibitor:	0.514
CYP3A4-substrate:	0.136

ADMET: Excretion

Clearance (CL):	3.254
Half-life (T1/2):	0.158

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.929
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.168
Rat Oral Acute Toxicity:	0.886
Maximum Recommended Daily Dose:	0.746
Skin Sensitization:	0.762
Carcinogencity:	0.8
Eye Corrosion:	0.003
Eye Irritation:	0.062
Respiratory Toxicity:	0.606

Download Data

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

Natural Product: NPC214236

Natural Product ID:	NPC214236
*Common Name:**	Laxifolin
IUPAC Name:	5-hydroxy-8-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one
Synonyms:
Standard InCHIKey:	WPIGCIDOOFISOE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H24O5/c1-14(2)5-10-18-23-17(11-12-25(3,4)30-23)22(28)21-19(27)13-20(29-24(18)21)15-6-8-16(26)9-7-15/h5-9,11-13,26,28H,10H2,1-4H3
SMILES:	CC(=CCc1c2OC(C)(C)C=Cc2c(c2c1oc(cc2=O)c1ccc(cc1)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2227763
PubChem CID:	15677602
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003504] 8-prenylated flavones

*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
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/S0031-9422(99)00103-X]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19969457]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21314138]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27553	Derris scandens	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
Others	64

Activity Type	# Activity
Cell Line	33
Organism	31

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	MNCC	=	3.1	uM	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	5.57	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	24.55	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	0.96	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	68.91	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	1.19	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	12.89	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	0.58	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	85.34	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	1.04	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	9.8	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	0.87	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	88.3	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	9.87	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	26.8	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	63.3	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	11.6	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	28.2	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	60.2	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	11.0	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	29.5	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	59.5	%	PMID[501716]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	20.0	%	PMID[501716]
NPT858	Cell Line	LNCaP	Homo sapiens	Activity	=	20.0	%	PMID[501716]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	20.0	%	PMID[501716]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	20.0	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	20.0	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	83.51	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	16.49	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	84.3	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	15.7	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	73.25	%	PMID[501716]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	26.75	%	PMID[501716]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	LC50	=	0.34	ug.mL-1	PMID[501714]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	mortality	=	100.0	%	PMID[501714]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	mortality	=	94.6	%	PMID[501714]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	mortality	=	92.3	%	PMID[501714]
NPT2745	Organism	Rhyzopertha dominica	Rhyzopertha dominica	LC50	=	0.34	ug.mL-1	PMID[501714]
NPT2745	Organism	Rhyzopertha dominica	Rhyzopertha dominica	mortality	=	92.0	%	PMID[501714]
NPT2745	Organism	Rhyzopertha dominica	Rhyzopertha dominica	mortality	=	90.8	%	PMID[501714]
NPT2745	Organism	Rhyzopertha dominica	Rhyzopertha dominica	mortality	=	89.3	%	PMID[501714]
NPT778	Organism	Sitophilus oryzae	Sitophilus oryzae	LC50	=	0.2	ug.mL-1	PMID[501714]
NPT778	Organism	Sitophilus oryzae	Sitophilus oryzae	mortality	=	100.0	%	PMID[501714]
NPT2721	Organism	Callosobruchus chinensis	Callosobruchus chinensis	LC50	=	0.39	ug.mL-1	PMID[501714]
NPT2721	Organism	Callosobruchus chinensis	Callosobruchus chinensis	mortality	=	96.4	%	PMID[501714]
NPT2721	Organism	Callosobruchus chinensis	Callosobruchus chinensis	mortality	=	93.2	%	PMID[501714]
NPT2721	Organism	Callosobruchus chinensis	Callosobruchus chinensis	mortality	=	88.8	%	PMID[501714]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	59.6	%	PMID[501715]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	24.9	%	PMID[501715]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	0.0	%	PMID[501715]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	2.3	%	PMID[501715]
NPT2747	Organism	Achaea janata	Achaea janata	mortality	=	12.0	%	PMID[501715]
NPT2747	Organism	Achaea janata	Achaea janata	mortality	=	27.4	%	PMID[501715]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	567.2	mg	PMID[501715]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	552.0	mg	PMID[501715]
NPT2747	Organism	Achaea janata	Achaea janata	TIME	=	256.8	hr	PMID[501715]
NPT2747	Organism	Achaea janata	Achaea janata	TIME	=	338.4	hr	PMID[501715]
NPT2747	Organism	Achaea janata	Achaea janata	mortality	=	20.6	%	PMID[501715]
NPT2747	Organism	Achaea janata	Achaea janata	mortality	=	25.2	%	PMID[501715]
NPT2747	Organism	Achaea janata	Achaea janata	TIME	=	204.0	hr	PMID[501715]
NPT2747	Organism	Achaea janata	Achaea janata	TIME	=	266.4	hr	PMID[501715]
NPT2747	Organism	Achaea janata	Achaea janata	AFI	=	2.6	%	PMID[501715]

☑ 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 NPC214236 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	408
0.1-0.2	1667
0.2-0.3	4321
0.3-0.4	11386
0.4-0.5	6799
0.5-0.6	4076
0.6-0.7	5959
0.7-0.8	4200
0.8-0.85	1910
0.85-0.9	1331
0.9-0.95	569
0.95-1	71

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC62840
1.0	High Similarity	NPC299080
1.0	High Similarity	NPC59739
1.0	High Similarity	NPC293852
1.0	High Similarity	NPC217083
1.0	High Similarity	NPC78803
0.9783	High Similarity	NPC38219
0.9783	High Similarity	NPC219915
0.9781	High Similarity	NPC156590
0.9781	High Similarity	NPC205006
0.9781	High Similarity	NPC118840
0.9781	High Similarity	NPC64908
0.9781	High Similarity	NPC147688
0.9779	High Similarity	NPC220062
0.9779	High Similarity	NPC96565
0.9779	High Similarity	NPC301217
0.9779	High Similarity	NPC303633
0.9779	High Similarity	NPC216978
0.9779	High Similarity	NPC55018
0.9714	High Similarity	NPC166757
0.9714	High Similarity	NPC97716
0.9714	High Similarity	NPC237635
0.9714	High Similarity	NPC104406
0.9714	High Similarity	NPC201731
0.9714	High Similarity	NPC14001
0.9714	High Similarity	NPC24673
0.9714	High Similarity	NPC79469
0.9712	High Similarity	NPC319752
0.971	High Similarity	NPC11561
0.971	High Similarity	NPC226636
0.9708	High Similarity	NPC172986
0.9708	High Similarity	NPC159275
0.9708	High Similarity	NPC241100
0.9708	High Similarity	NPC270883
0.9708	High Similarity	NPC305355
0.9708	High Similarity	NPC261227
0.9708	High Similarity	NPC475680
0.9708	High Similarity	NPC150522
0.9708	High Similarity	NPC235239
0.9706	High Similarity	NPC201395
0.9645	High Similarity	NPC244407
0.9645	High Similarity	NPC266572
0.9645	High Similarity	NPC189087
0.9645	High Similarity	NPC321623
0.9645	High Similarity	NPC161191
0.9645	High Similarity	NPC6511
0.9643	High Similarity	NPC20488
0.9643	High Similarity	NPC176229
0.9643	High Similarity	NPC111786
0.9643	High Similarity	NPC474161
0.9643	High Similarity	NPC312973
0.9643	High Similarity	NPC220418
0.9643	High Similarity	NPC470647
0.9643	High Similarity	NPC301276
0.9643	High Similarity	NPC246948
0.9643	High Similarity	NPC54577
0.9643	High Similarity	NPC475052
0.9643	High Similarity	NPC88964
0.9643	High Similarity	NPC476088
0.9643	High Similarity	NPC57470
0.9643	High Similarity	NPC267375
0.9643	High Similarity	NPC195621
0.9643	High Similarity	NPC142405
0.9643	High Similarity	NPC67805
0.9643	High Similarity	NPC83357
0.9643	High Similarity	NPC214774
0.9638	High Similarity	NPC110969
0.9638	High Similarity	NPC14871
0.9638	High Similarity	NPC103362
0.9638	High Similarity	NPC282300
0.9635	High Similarity	NPC18260
0.9635	High Similarity	NPC78913
0.9635	High Similarity	NPC217186
0.9635	High Similarity	NPC53181
0.9577	High Similarity	NPC5173
0.9574	High Similarity	NPC296998
0.9574	High Similarity	NPC180477
0.9574	High Similarity	NPC473077
0.9574	High Similarity	NPC297886
0.9574	High Similarity	NPC23728
0.9574	High Similarity	NPC283234
0.9574	High Similarity	NPC110303
0.9574	High Similarity	NPC249942
0.9571	High Similarity	NPC257236
0.9571	High Similarity	NPC278175
0.9571	High Similarity	NPC234629
0.9571	High Similarity	NPC311741
0.9568	High Similarity	NPC200694
0.9568	High Similarity	NPC144499
0.9565	High Similarity	NPC69769
0.9562	High Similarity	NPC470668
0.9562	High Similarity	NPC470669
0.9562	High Similarity	NPC17848
0.9559	High Similarity	NPC13408
0.951	High Similarity	NPC471984
0.951	High Similarity	NPC188403
0.9507	High Similarity	NPC132592
0.9507	High Similarity	NPC296869
0.9507	High Similarity	NPC161864
0.9507	High Similarity	NPC469933
0.9507	High Similarity	NPC208303
0.9507	High Similarity	NPC160821
0.9504	High Similarity	NPC124729
0.9504	High Similarity	NPC329678
0.95	High Similarity	NPC190637
0.95	High Similarity	NPC478086
0.95	High Similarity	NPC212932
0.95	High Similarity	NPC18585
0.95	High Similarity	NPC166138
0.95	High Similarity	NPC106985
0.95	High Similarity	NPC9117
0.95	High Similarity	NPC293053
0.95	High Similarity	NPC11700
0.95	High Similarity	NPC24821
0.95	High Similarity	NPC316816
0.95	High Similarity	NPC214166
0.9493	High Similarity	NPC23257
0.9489	High Similarity	NPC157855
0.9441	High Similarity	NPC469932
0.9437	High Similarity	NPC140120
0.9433	High Similarity	NPC131568
0.9433	High Similarity	NPC326500
0.9433	High Similarity	NPC209040
0.9433	High Similarity	NPC216538
0.9433	High Similarity	NPC469953
0.9433	High Similarity	NPC131579
0.9433	High Similarity	NPC273538
0.9429	High Similarity	NPC148757
0.9429	High Similarity	NPC76372
0.9429	High Similarity	NPC32739
0.9429	High Similarity	NPC66515
0.9429	High Similarity	NPC473042
0.9429	High Similarity	NPC166482
0.9429	High Similarity	NPC107572
0.9429	High Similarity	NPC324134
0.9429	High Similarity	NPC161506
0.9429	High Similarity	NPC36181
0.9429	High Similarity	NPC324436
0.9429	High Similarity	NPC194432
0.9429	High Similarity	NPC167624
0.9429	High Similarity	NPC37496
0.9429	High Similarity	NPC166934
0.9429	High Similarity	NPC220998
0.9429	High Similarity	NPC76338
0.9429	High Similarity	NPC227579
0.9429	High Similarity	NPC228504
0.9429	High Similarity	NPC78
0.9429	High Similarity	NPC10937
0.9429	High Similarity	NPC223500
0.9429	High Similarity	NPC328164
0.9429	High Similarity	NPC177354
0.9429	High Similarity	NPC64915
0.9429	High Similarity	NPC265040
0.9429	High Similarity	NPC40833
0.9429	High Similarity	NPC125855
0.9429	High Similarity	NPC182852
0.9429	High Similarity	NPC296917
0.9429	High Similarity	NPC1089
0.9429	High Similarity	NPC306829
0.9424	High Similarity	NPC471587
0.942	High Similarity	NPC248995
0.942	High Similarity	NPC272844
0.942	High Similarity	NPC131130
0.942	High Similarity	NPC254168
0.9416	High Similarity	NPC29353
0.9416	High Similarity	NPC124784
0.9416	High Similarity	NPC127447
0.9416	High Similarity	NPC161196
0.9416	High Similarity	NPC231772
0.9416	High Similarity	NPC473887
0.9416	High Similarity	NPC194281
0.9416	High Similarity	NPC234133
0.9416	High Similarity	NPC174999
0.9416	High Similarity	NPC47815
0.9379	High Similarity	NPC45934
0.9375	High Similarity	NPC471115
0.9375	High Similarity	NPC472633
0.9375	High Similarity	NPC29777
0.9375	High Similarity	NPC151973
0.9366	High Similarity	NPC5820
0.9366	High Similarity	NPC285630
0.9366	High Similarity	NPC154217
0.9366	High Similarity	NPC127059
0.9366	High Similarity	NPC470131
0.9366	High Similarity	NPC470134
0.9366	High Similarity	NPC178343
0.9366	High Similarity	NPC477955
0.9366	High Similarity	NPC473078
0.9366	High Similarity	NPC470133
0.9366	High Similarity	NPC109183
0.9366	High Similarity	NPC470132
0.9366	High Similarity	NPC306488
0.9362	High Similarity	NPC81697
0.9362	High Similarity	NPC188632
0.9362	High Similarity	NPC185276
0.9362	High Similarity	NPC91560
0.9362	High Similarity	NPC149026
0.9362	High Similarity	NPC75049
0.9362	High Similarity	NPC107177
0.9362	High Similarity	NPC143896

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 NPC214236 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	957
0.2-0.3	1471
0.3-0.4	2678
0.4-0.5	1959
0.5-0.6	1167
0.6-0.7	364
0.7-0.8	123
0.8-0.85	39
0.85-0.9	22
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9571	High Similarity	NPD7410	Clinical (unspecified phase)
0.9433	High Similarity	NPD4378	Clinical (unspecified phase)
0.9071	High Similarity	NPD1550	Clinical (unspecified phase)
0.9071	High Similarity	NPD1552	Clinical (unspecified phase)
0.9007	High Similarity	NPD1549	Phase 2
0.8929	High Similarity	NPD1510	Phase 2
0.8919	High Similarity	NPD7411	Suspended
0.8913	High Similarity	NPD1240	Approved
0.8867	High Similarity	NPD8443	Clinical (unspecified phase)
0.8865	High Similarity	NPD2796	Approved
0.8851	High Similarity	NPD4380	Phase 2
0.88	High Similarity	NPD2393	Clinical (unspecified phase)
0.8786	High Similarity	NPD1607	Approved
0.8699	High Similarity	NPD1511	Approved
0.8627	High Similarity	NPD7075	Discontinued
0.8621	High Similarity	NPD3750	Approved
0.8609	High Similarity	NPD6801	Discontinued
0.8581	High Similarity	NPD1512	Approved
0.8553	High Similarity	NPD7819	Suspended
0.8553	High Similarity	NPD7096	Clinical (unspecified phase)
0.8553	High Similarity	NPD2801	Approved
0.8506	High Similarity	NPD4381	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD1934	Approved
0.8446	Intermediate Similarity	NPD6799	Approved
0.8442	Intermediate Similarity	NPD7768	Phase 2
0.8425	Intermediate Similarity	NPD2800	Approved
0.8425	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD3749	Approved
0.8375	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6959	Discontinued
0.8299	Intermediate Similarity	NPD1243	Approved
0.8278	Intermediate Similarity	NPD5403	Approved
0.8276	Intermediate Similarity	NPD3748	Approved
0.8264	Intermediate Similarity	NPD6651	Approved
0.8239	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD6599	Discontinued
0.8231	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD3882	Suspended
0.8187	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6166	Phase 2
0.8151	Intermediate Similarity	NPD2799	Discontinued
0.8146	Intermediate Similarity	NPD5401	Approved
0.8141	Intermediate Similarity	NPD3817	Phase 2
0.8112	Intermediate Similarity	NPD2313	Discontinued
0.8095	Intermediate Similarity	NPD2935	Discontinued
0.8095	Intermediate Similarity	NPD1551	Phase 2
0.8061	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD5494	Approved
0.8041	Intermediate Similarity	NPD2344	Approved
0.8039	Intermediate Similarity	NPD920	Approved
0.8037	Intermediate Similarity	NPD7054	Approved
0.8014	Intermediate Similarity	NPD1203	Approved
0.8013	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7472	Approved
0.7988	Intermediate Similarity	NPD7074	Phase 3
0.7986	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD3268	Approved
0.7975	Intermediate Similarity	NPD3818	Discontinued
0.7973	Intermediate Similarity	NPD6099	Approved
0.7973	Intermediate Similarity	NPD6100	Approved
0.795	Intermediate Similarity	NPD6232	Discontinued
0.7945	Intermediate Similarity	NPD5124	Phase 1
0.7945	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD3225	Approved
0.7939	Intermediate Similarity	NPD5953	Discontinued
0.7939	Intermediate Similarity	NPD6797	Phase 2
0.7927	Intermediate Similarity	NPD7286	Phase 2
0.7914	Intermediate Similarity	NPD7473	Discontinued
0.7911	Intermediate Similarity	NPD5402	Approved
0.7908	Intermediate Similarity	NPD2532	Approved
0.7908	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD2534	Approved
0.7908	Intermediate Similarity	NPD2533	Approved
0.7905	Intermediate Similarity	NPD7033	Discontinued
0.7905	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7251	Discontinued
0.7887	Intermediate Similarity	NPD2797	Approved
0.7881	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD422	Phase 1
0.7847	Intermediate Similarity	NPD4908	Phase 1
0.7844	Intermediate Similarity	NPD7808	Phase 3
0.7843	Intermediate Similarity	NPD7390	Discontinued
0.7832	Intermediate Similarity	NPD2798	Approved
0.7829	Intermediate Similarity	NPD2309	Approved
0.7826	Intermediate Similarity	NPD1548	Phase 1
0.7821	Intermediate Similarity	NPD3226	Approved
0.7801	Intermediate Similarity	NPD9717	Approved
0.7785	Intermediate Similarity	NPD4308	Phase 3
0.7784	Intermediate Similarity	NPD6559	Discontinued
0.7763	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD943	Approved
0.7738	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD6832	Phase 2
0.7711	Intermediate Similarity	NPD5844	Phase 1
0.7701	Intermediate Similarity	NPD4363	Phase 3
0.7701	Intermediate Similarity	NPD4360	Phase 2
0.7682	Intermediate Similarity	NPD2346	Discontinued
0.7671	Intermediate Similarity	NPD4625	Phase 3
0.7654	Intermediate Similarity	NPD919	Approved
0.7647	Intermediate Similarity	NPD4628	Phase 3
0.7639	Intermediate Similarity	NPD3267	Approved
0.7639	Intermediate Similarity	NPD3266	Approved
0.7614	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD1610	Phase 2
0.7582	Intermediate Similarity	NPD2654	Approved
0.7578	Intermediate Similarity	NPD4288	Approved
0.7561	Intermediate Similarity	NPD1247	Approved
0.7557	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD4361	Phase 2
0.7547	Intermediate Similarity	NPD6585	Discontinued
0.7517	Intermediate Similarity	NPD4307	Phase 2
0.7516	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD1296	Phase 2
0.75	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3926	Phase 2
0.7456	Intermediate Similarity	NPD1729	Discontinued
0.7431	Intermediate Similarity	NPD1608	Approved
0.7431	Intermediate Similarity	NPD3972	Approved
0.7412	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5890	Approved
0.7391	Intermediate Similarity	NPD5889	Approved
0.7386	Intermediate Similarity	NPD5406	Approved
0.7386	Intermediate Similarity	NPD5405	Approved
0.7386	Intermediate Similarity	NPD5404	Approved
0.7386	Intermediate Similarity	NPD5408	Approved
0.7383	Intermediate Similarity	NPD3764	Approved
0.7379	Intermediate Similarity	NPD4749	Approved
0.7375	Intermediate Similarity	NPD7458	Discontinued
0.7371	Intermediate Similarity	NPD4287	Approved
0.7365	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1201	Approved
0.7358	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1933	Approved
0.7342	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7584	Approved
0.7337	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD9545	Approved
0.7321	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7003	Approved
0.7305	Intermediate Similarity	NPD5710	Approved
0.7305	Intermediate Similarity	NPD9493	Approved
0.7305	Intermediate Similarity	NPD5711	Approved
0.7297	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5049	Phase 3
0.7288	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1470	Approved
0.7279	Intermediate Similarity	NPD1164	Approved
0.7267	Intermediate Similarity	NPD411	Approved
0.7267	Intermediate Similarity	NPD6798	Discontinued
0.7267	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2354	Approved
0.7256	Intermediate Similarity	NPD2296	Approved
0.7237	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD447	Suspended
0.7226	Intermediate Similarity	NPD1471	Phase 3
0.7222	Intermediate Similarity	NPD17	Approved
0.7214	Intermediate Similarity	NPD1241	Discontinued
0.7202	Intermediate Similarity	NPD7229	Phase 3
0.7198	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1481	Phase 2
0.7171	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1613	Approved
0.717	Intermediate Similarity	NPD7212	Phase 2
0.717	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7213	Phase 3
0.7168	Intermediate Similarity	NPD6104	Discontinued
0.7153	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3751	Discontinued
0.7134	Intermediate Similarity	NPD7577	Discontinued
0.7134	Intermediate Similarity	NPD6844	Discontinued
0.7133	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7447	Phase 1
0.7124	Intermediate Similarity	NPD230	Phase 1
0.7123	Intermediate Similarity	NPD1535	Discovery
0.7118	Intermediate Similarity	NPD2403	Approved
0.7115	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2353	Approved
0.7115	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1019	Discontinued
0.7101	Intermediate Similarity	NPD3787	Discontinued
0.7097	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD8312	Approved
0.7086	Intermediate Similarity	NPD8313	Approved
0.707	Intermediate Similarity	NPD2424	Discontinued
0.7051	Intermediate Similarity	NPD4476	Approved
0.7051	Intermediate Similarity	NPD4477	Approved
0.7044	Intermediate Similarity	NPD3887	Approved
0.7044	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7199	Phase 2
0.7035	Intermediate Similarity	NPD7177	Discontinued
0.7035	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1652	Phase 2
0.7021	Intermediate Similarity	NPD5535	Approved
0.7019	Intermediate Similarity	NPD4662	Approved
0.7019	Intermediate Similarity	NPD4661	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