NPASS Compound

Structure

CID255106 OpenBabel06191716062D 21 23 0 0 1 0 0 0 0 0999 V2000 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 4.3301 -2.5000 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 3.4641 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 4.3301 -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 0.0000 -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 1 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 0.8660 0.5000 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 2.5981 1.5000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 9 2 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 12 1 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 10 14 1 0 0 0 0 10 17 2 0 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 12 9 1 1 0 0 0 12 21 1 0 0 0 0 13 14 2 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 15 16 2 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.08
Volume:	285.119
LogP:	2.905
LogD:	2.632
LogS:	-3.802
# Rotatable Bonds:	2
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.887
Synthetic Accessibility Score:	2.833
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.89
MDCK Permeability:	1.9654145944514312e-05
Pgp-inhibitor:	0.743
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.161

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.06
Plasma Protein Binding (PPB):	96.59146118164062%
Volume Distribution (VD):	0.626
Pgp-substrate:	5.886930465698242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.841
CYP1A2-substrate:	0.717
CYP2C19-inhibitor:	0.782
CYP2C19-substrate:	0.314
CYP2C9-inhibitor:	0.829
CYP2C9-substrate:	0.908
CYP2D6-inhibitor:	0.768
CYP2D6-substrate:	0.513
CYP3A4-inhibitor:	0.617
CYP3A4-substrate:	0.232

ADMET: Excretion

Clearance (CL):	12.675
Half-life (T1/2):	0.519

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.339
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.153
Rat Oral Acute Toxicity:	0.869
Maximum Recommended Daily Dose:	0.091
Skin Sensitization:	0.79
Carcinogencity:	0.639
Eye Corrosion:	0.009
Eye Irritation:	0.922
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC255106

Natural Product ID:	NPC255106
*Common Name:**	Dihydrooroxylin A
IUPAC Name:	(2S)-5,7-dihydroxy-6-methoxy-2-phenyl-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	QUAPPCXFYKSDSV-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C16H14O5/c1-20-16-11(18)8-13-14(15(16)19)10(17)7-12(21-13)9-5-3-2-4-6-9/h2-6,8,12,18-19H,7H2,1H3/t12-/m0/s1
SMILES:	COc1c(O)cc2c(c1O)C(=O)C[C@H](O2)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253465
PubChem CID:	177032
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002591] 6-O-methylated flavonoids

*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
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruit	n.a.	n.a.	DOI[10.1016/S0963-9969(99)00095-2]
NPO13813	Durio carinatus	Species	Malvaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np100332v]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713409]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	Brazilian	n.a.	PMID[17950610]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	Brazilian	n.a.	PMID[18440233]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19555121]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19555121]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19948405]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21381697]
NPO25983	Pisonia aculeata	Species	Nyctaginaceae	Eukaryota	n.a.	root	n.a.	PMID[21542597]
NPO25983	Pisonia aculeata	Species	Nyctaginaceae	Eukaryota	n.a.	stem	n.a.	PMID[21542597]
NPO25983	Pisonia aculeata	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21542597]
NPO17254	Streptomyces anulatus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23423168]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23672042]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	aerial part	n.a.	n.a.	PMID[25442304]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26938776]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[32525315]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruit	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Leaf	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Seed	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.		n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruits	n.a.		Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruits	n.a.		Database[Phenol-Explorer]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.		Database[Phenol-Explorer]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23802	Styrax formosanus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8733	Duttaphrynus melanostictus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8733	Duttaphrynus melanostictus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13813	Durio carinatus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16985	Tribulus alatus	Species	Muricidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18604	Nassauvia pyramidalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23802	Styrax formosanus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5529	Diaporthe longicolla	Species	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9929	Amomum sceptrum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17254	Streptomyces anulatus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25983	Pisonia aculeata	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8548	Zanthoxylum beecheyanum	Species	Rutaceae	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	6
MIC	1
Others	1

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	CD100	>	100.0	uM	PMID[521159]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	38000.0	nM	PMID[521160]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	39300.0	nM	PMID[521160]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	47600.0	nM	PMID[521160]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	49000.0	nM	PMID[521160]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	72600.0	nM	PMID[521160]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	82700.0	nM	PMID[521160]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	50.0	ug.mL-1	PMID[521163]

☑ 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 NPC255106 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	412
0.1-0.2	1664
0.2-0.3	4454
0.3-0.4	10476
0.4-0.5	7329
0.5-0.6	3431
0.6-0.7	4706
0.7-0.8	5377
0.8-0.85	2537
0.85-0.9	1564
0.9-0.95	642
0.95-1	105

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC235165
0.9933	High Similarity	NPC162869
0.9933	High Similarity	NPC474208
0.9933	High Similarity	NPC156057
0.9933	High Similarity	NPC99597
0.9933	High Similarity	NPC48208
0.9933	High Similarity	NPC475267
0.9933	High Similarity	NPC474836
0.9933	High Similarity	NPC210084
0.9801	High Similarity	NPC263449
0.98	High Similarity	NPC472911
0.98	High Similarity	NPC245758
0.98	High Similarity	NPC472914
0.98	High Similarity	NPC472910
0.98	High Similarity	NPC472913
0.98	High Similarity	NPC222814
0.98	High Similarity	NPC96167
0.9799	High Similarity	NPC2928
0.9799	High Similarity	NPC37392
0.9797	High Similarity	NPC180234
0.9797	High Similarity	NPC302950
0.9797	High Similarity	NPC219582
0.9797	High Similarity	NPC120537
0.9797	High Similarity	NPC236637
0.9797	High Similarity	NPC199100
0.9737	High Similarity	NPC308992
0.9735	High Similarity	NPC250214
0.9735	High Similarity	NPC95936
0.9733	High Similarity	NPC472916
0.9732	High Similarity	NPC167091
0.9732	High Similarity	NPC271779
0.9732	High Similarity	NPC18727
0.9732	High Similarity	NPC206238
0.9732	High Similarity	NPC292214
0.9732	High Similarity	NPC88645
0.973	High Similarity	NPC204515
0.973	High Similarity	NPC117579
0.9669	High Similarity	NPC470402
0.9669	High Similarity	NPC469584
0.9669	High Similarity	NPC223787
0.9669	High Similarity	NPC78225
0.9667	High Similarity	NPC472909
0.9667	High Similarity	NPC213622
0.9664	High Similarity	NPC57030
0.9664	High Similarity	NPC120163
0.9664	High Similarity	NPC301323
0.9664	High Similarity	NPC275722
0.9664	High Similarity	NPC83508
0.9664	High Similarity	NPC25270
0.9664	High Similarity	NPC101996
0.9664	High Similarity	NPC241498
0.9664	High Similarity	NPC162313
0.9664	High Similarity	NPC161277
0.9664	High Similarity	NPC100887
0.9664	High Similarity	NPC222830
0.9664	High Similarity	NPC256283
0.9664	High Similarity	NPC293183
0.9664	High Similarity	NPC239128
0.9664	High Similarity	NPC188203
0.9664	High Similarity	NPC198826
0.9664	High Similarity	NPC39007
0.9664	High Similarity	NPC275836
0.9664	High Similarity	NPC131624
0.9664	High Similarity	NPC156222
0.9664	High Similarity	NPC187498
0.9664	High Similarity	NPC212678
0.9664	High Similarity	NPC71334
0.9662	High Similarity	NPC62042
0.9662	High Similarity	NPC61620
0.9608	High Similarity	NPC266314
0.9605	High Similarity	NPC152904
0.9603	High Similarity	NPC195796
0.9603	High Similarity	NPC291878
0.9603	High Similarity	NPC320825
0.9603	High Similarity	NPC191146
0.9603	High Similarity	NPC13858
0.9603	High Similarity	NPC278778
0.9603	High Similarity	NPC68093
0.9603	High Similarity	NPC35038
0.9603	High Similarity	NPC201837
0.9603	High Similarity	NPC326037
0.96	High Similarity	NPC183878
0.96	High Similarity	NPC472915
0.96	High Similarity	NPC22519
0.96	High Similarity	NPC160951
0.96	High Similarity	NPC231018
0.96	High Similarity	NPC274327
0.96	High Similarity	NPC145379
0.96	High Similarity	NPC255350
0.96	High Similarity	NPC47781
0.96	High Similarity	NPC176775
0.96	High Similarity	NPC69394
0.9597	High Similarity	NPC251110
0.9597	High Similarity	NPC171010
0.9597	High Similarity	NPC31363
0.9597	High Similarity	NPC149614
0.9548	High Similarity	NPC224280
0.9539	High Similarity	NPC27337
0.9539	High Similarity	NPC291508
0.9539	High Similarity	NPC299520
0.9539	High Similarity	NPC241904
0.9539	High Similarity	NPC181960
0.9539	High Similarity	NPC472598
0.9539	High Similarity	NPC129684
0.9539	High Similarity	NPC36852
0.9539	High Similarity	NPC262286
0.9539	High Similarity	NPC471479
0.9539	High Similarity	NPC300727
0.9539	High Similarity	NPC52530
0.9539	High Similarity	NPC471515
0.9539	High Similarity	NPC474055
0.9536	High Similarity	NPC227325
0.9536	High Similarity	NPC92659
0.9536	High Similarity	NPC20830
0.9536	High Similarity	NPC183597
0.9536	High Similarity	NPC477503
0.9536	High Similarity	NPC44079
0.9536	High Similarity	NPC2476
0.9536	High Similarity	NPC201136
0.9536	High Similarity	NPC256612
0.9536	High Similarity	NPC167815
0.9536	High Similarity	NPC146165
0.9536	High Similarity	NPC470327
0.9536	High Similarity	NPC45849
0.9536	High Similarity	NPC200761
0.9536	High Similarity	NPC138360
0.9536	High Similarity	NPC280339
0.9536	High Similarity	NPC196439
0.9536	High Similarity	NPC128863
0.9536	High Similarity	NPC4455
0.9536	High Similarity	NPC201451
0.9536	High Similarity	NPC26227
0.9536	High Similarity	NPC163780
0.9536	High Similarity	NPC50715
0.9533	High Similarity	NPC291802
0.9533	High Similarity	NPC260979
0.9533	High Similarity	NPC209487
0.9533	High Similarity	NPC477231
0.9533	High Similarity	NPC181209
0.9533	High Similarity	NPC131266
0.9533	High Similarity	NPC35763
0.9533	High Similarity	NPC257648
0.9533	High Similarity	NPC472912
0.9533	High Similarity	NPC100971
0.9533	High Similarity	NPC216769
0.9533	High Similarity	NPC100263
0.9533	High Similarity	NPC245382
0.9533	High Similarity	NPC142540
0.9533	High Similarity	NPC269451
0.9533	High Similarity	NPC121522
0.953	High Similarity	NPC184136
0.953	High Similarity	NPC29231
0.953	High Similarity	NPC338131
0.953	High Similarity	NPC179183
0.953	High Similarity	NPC306821
0.953	High Similarity	NPC248102
0.9527	High Similarity	NPC294852
0.9527	High Similarity	NPC188679
0.9527	High Similarity	NPC276930
0.9527	High Similarity	NPC321011
0.9484	High Similarity	NPC475985
0.9484	High Similarity	NPC470178
0.9481	High Similarity	NPC173137
0.9477	High Similarity	NPC476242
0.9477	High Similarity	NPC55738
0.9477	High Similarity	NPC329091
0.9474	High Similarity	NPC471500
0.9474	High Similarity	NPC303255
0.9474	High Similarity	NPC98661
0.9474	High Similarity	NPC245546
0.9474	High Similarity	NPC138243
0.9474	High Similarity	NPC43243
0.9474	High Similarity	NPC274730
0.9474	High Similarity	NPC472626
0.9474	High Similarity	NPC474638
0.9474	High Similarity	NPC470328
0.9474	High Similarity	NPC247017
0.9474	High Similarity	NPC266960
0.9474	High Similarity	NPC49824
0.9474	High Similarity	NPC317383
0.9474	High Similarity	NPC209614
0.9474	High Similarity	NPC250922
0.947	High Similarity	NPC192083
0.947	High Similarity	NPC213896
0.947	High Similarity	NPC75279
0.947	High Similarity	NPC276409
0.947	High Similarity	NPC280937
0.947	High Similarity	NPC124714
0.947	High Similarity	NPC469550
0.947	High Similarity	NPC250822
0.9467	High Similarity	NPC45291
0.9467	High Similarity	NPC226973
0.9467	High Similarity	NPC19980
0.9467	High Similarity	NPC208043
0.9463	High Similarity	NPC200221
0.9463	High Similarity	NPC52005
0.9463	High Similarity	NPC216318
0.9463	High Similarity	NPC183950
0.9463	High Similarity	NPC259713
0.9463	High Similarity	NPC296197

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 NPC255106 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	947
0.2-0.3	1820
0.3-0.4	2643
0.4-0.5	1726
0.5-0.6	970
0.6-0.7	484
0.7-0.8	132
0.8-0.85	35
0.85-0.9	13
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9797	High Similarity	NPD1934	Approved
0.96	High Similarity	NPD2801	Approved
0.947	High Similarity	NPD2393	Clinical (unspecified phase)
0.9177	High Similarity	NPD6168	Clinical (unspecified phase)
0.9177	High Similarity	NPD6166	Phase 2
0.9177	High Similarity	NPD6167	Clinical (unspecified phase)
0.9128	High Similarity	NPD1511	Approved
0.9097	High Similarity	NPD3882	Suspended
0.9007	High Similarity	NPD1512	Approved
0.8951	High Similarity	NPD7074	Phase 3
0.8944	High Similarity	NPD3818	Discontinued
0.8924	High Similarity	NPD5494	Approved
0.8902	High Similarity	NPD4338	Clinical (unspecified phase)
0.8889	High Similarity	NPD7054	Approved
0.8854	High Similarity	NPD4868	Clinical (unspecified phase)
0.8851	High Similarity	NPD1550	Clinical (unspecified phase)
0.8851	High Similarity	NPD1552	Clinical (unspecified phase)
0.8834	High Similarity	NPD7472	Approved
0.8792	High Similarity	NPD1549	Phase 2
0.879	High Similarity	NPD3817	Phase 2
0.8667	High Similarity	NPD6797	Phase 2
0.8654	High Similarity	NPD4380	Phase 2
0.8614	High Similarity	NPD7251	Discontinued
0.8571	High Similarity	NPD4378	Clinical (unspecified phase)
0.8563	High Similarity	NPD7808	Phase 3
0.8562	High Similarity	NPD7075	Discontinued
0.8562	High Similarity	NPD4381	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1510	Phase 2
0.8434	Intermediate Similarity	NPD5844	Phase 1
0.8411	Intermediate Similarity	NPD2796	Approved
0.8375	Intermediate Similarity	NPD1465	Phase 2
0.8354	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD5402	Approved
0.8322	Intermediate Similarity	NPD943	Approved
0.8322	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1240	Approved
0.8322	Intermediate Similarity	NPD1613	Approved
0.8313	Intermediate Similarity	NPD7473	Discontinued
0.8293	Intermediate Similarity	NPD1247	Approved
0.8269	Intermediate Similarity	NPD6799	Approved
0.8261	Intermediate Similarity	NPD7819	Suspended
0.8214	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD1607	Approved
0.8199	Intermediate Similarity	NPD6801	Discontinued
0.8182	Intermediate Similarity	NPD6959	Discontinued
0.8176	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7411	Suspended
0.8108	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6599	Discontinued
0.807	Intermediate Similarity	NPD6559	Discontinued
0.8026	Intermediate Similarity	NPD230	Phase 1
0.8	Intermediate Similarity	NPD3027	Phase 3
0.7976	Intermediate Similarity	NPD3926	Phase 2
0.7952	Intermediate Similarity	NPD919	Approved
0.7949	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD2935	Discontinued
0.7908	Intermediate Similarity	NPD447	Suspended
0.7898	Intermediate Similarity	NPD2800	Approved
0.7892	Intermediate Similarity	NPD3749	Approved
0.7888	Intermediate Similarity	NPD5403	Approved
0.7875	Intermediate Similarity	NPD5401	Approved
0.7853	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD3750	Approved
0.784	Intermediate Similarity	NPD1653	Approved
0.7836	Intermediate Similarity	NPD3751	Discontinued
0.7824	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1551	Phase 2
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2534	Approved
0.7764	Intermediate Similarity	NPD2532	Approved
0.7764	Intermediate Similarity	NPD2533	Approved
0.7756	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD9494	Approved
0.7738	Intermediate Similarity	NPD6234	Discontinued
0.7736	Intermediate Similarity	NPD4628	Phase 3
0.7725	Intermediate Similarity	NPD7768	Phase 2
0.7712	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD3787	Discontinued
0.7688	Intermediate Similarity	NPD6190	Approved
0.7684	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1933	Approved
0.7673	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD920	Approved
0.7667	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2344	Approved
0.7647	Intermediate Similarity	NPD7199	Phase 2
0.7625	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6100	Approved
0.7595	Intermediate Similarity	NPD6099	Approved
0.7593	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3226	Approved
0.7558	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2346	Discontinued
0.7546	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD37	Approved
0.7532	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3748	Approved
0.7529	Intermediate Similarity	NPD7228	Approved
0.7515	Intermediate Similarity	NPD4967	Phase 2
0.7515	Intermediate Similarity	NPD4966	Approved
0.7515	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD5953	Discontinued
0.7486	Intermediate Similarity	NPD7286	Phase 2
0.7484	Intermediate Similarity	NPD2313	Discontinued
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2309	Approved
0.7468	Intermediate Similarity	NPD4908	Phase 1
0.7467	Intermediate Similarity	NPD1610	Phase 2
0.7458	Intermediate Similarity	NPD7685	Pre-registration
0.7453	Intermediate Similarity	NPD1243	Approved
0.744	Intermediate Similarity	NPD6844	Discontinued
0.7423	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2799	Discontinued
0.7416	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6651	Approved
0.7403	Intermediate Similarity	NPD2861	Phase 2
0.7386	Intermediate Similarity	NPD1203	Approved
0.738	Intermediate Similarity	NPD6776	Approved
0.738	Intermediate Similarity	NPD6779	Approved
0.738	Intermediate Similarity	NPD6780	Approved
0.738	Intermediate Similarity	NPD6781	Approved
0.738	Intermediate Similarity	NPD6778	Approved
0.738	Intermediate Similarity	NPD6782	Approved
0.738	Intermediate Similarity	NPD6777	Approved
0.7374	Intermediate Similarity	NPD8313	Approved
0.7374	Intermediate Similarity	NPD8312	Approved
0.7372	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5242	Approved
0.7353	Intermediate Similarity	NPD5353	Approved
0.7348	Intermediate Similarity	NPD8434	Phase 2
0.7342	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6233	Phase 2
0.7315	Intermediate Similarity	NPD1548	Phase 1
0.7312	Intermediate Similarity	NPD7033	Discontinued
0.7303	Intermediate Similarity	NPD9269	Phase 2
0.7301	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD5710	Approved
0.7299	Intermediate Similarity	NPD5711	Approved
0.7297	Intermediate Similarity	NPD4363	Phase 3
0.7297	Intermediate Similarity	NPD4360	Phase 2
0.7278	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7390	Discontinued
0.7263	Intermediate Similarity	NPD7435	Discontinued
0.7261	Intermediate Similarity	NPD6798	Discontinued
0.7253	Intermediate Similarity	NPD8150	Discontinued
0.7244	Intermediate Similarity	NPD6832	Phase 2
0.7229	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD9717	Approved
0.719	Intermediate Similarity	NPD1608	Approved
0.7179	Intermediate Similarity	NPD7783	Phase 2
0.7179	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2424	Discontinued
0.7176	Intermediate Similarity	NPD6386	Approved
0.7176	Intermediate Similarity	NPD6385	Approved
0.7173	Intermediate Similarity	NPD7697	Approved
0.7173	Intermediate Similarity	NPD7696	Phase 3
0.7173	Intermediate Similarity	NPD7698	Approved
0.7165	Intermediate Similarity	NPD8151	Discontinued
0.7152	Intermediate Similarity	NPD3268	Approved
0.715	Intermediate Similarity	NPD7584	Approved
0.7135	Intermediate Similarity	NPD7870	Phase 2
0.7135	Intermediate Similarity	NPD7871	Phase 2
0.7134	Intermediate Similarity	NPD1652	Phase 2
0.7127	Intermediate Similarity	NPD7549	Discontinued
0.7125	Intermediate Similarity	NPD6355	Discontinued
0.7124	Intermediate Similarity	NPD422	Phase 1
0.712	Intermediate Similarity	NPD6823	Phase 2
0.7119	Intermediate Similarity	NPD2403	Approved
0.7117	Intermediate Similarity	NPD7266	Discontinued
0.7115	Intermediate Similarity	NPD2798	Approved
0.7113	Intermediate Similarity	NPD7701	Phase 2
0.7112	Intermediate Similarity	NPD6534	Approved
0.7112	Intermediate Similarity	NPD6535	Approved
0.7102	Intermediate Similarity	NPD7229	Phase 3
0.71	Intermediate Similarity	NPD2899	Discontinued
0.7099	Intermediate Similarity	NPD4308	Phase 3
0.7089	Intermediate Similarity	NPD4625	Phase 3
0.7072	Intermediate Similarity	NPD7240	Approved
0.707	Intermediate Similarity	NPD3018	Phase 2
0.7066	Intermediate Similarity	NPD4357	Discontinued
0.7059	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2797	Approved
0.7051	Intermediate Similarity	NPD1470	Approved
0.7044	Intermediate Similarity	NPD411	Approved
0.7041	Intermediate Similarity	NPD7874	Approved
0.7041	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD9268	Approved
0.7032	Intermediate Similarity	NPD4749	Approved
0.703	Intermediate Similarity	NPD2654	Approved
0.7024	Intermediate Similarity	NPD4661	Approved
0.7024	Intermediate Similarity	NPD4662	Approved
0.702	Intermediate Similarity	NPD5536	Phase 2

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