NPASS Compound

Structure

CID131725 OpenBabel06191715492D 21 24 0 0 1 0 0 0 0 0999 V2000 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0380 -1.6121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0326 -1.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4393 -0.8031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 2.3660 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 18 1 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 10 13 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 8 1 1 0 0 0 14 16 1 0 0 0 0 14 21 1 0 0 0 0 15 17 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.08
Volume:	279.199
LogP:	3.303
LogD:	3.083
LogS:	-4.232
# Rotatable Bonds:	3
TPSA:	65.11
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.547
Synthetic Accessibility Score:	3.259
Fsp3:	0.312
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.748
MDCK Permeability:	3.251512680435553e-05
Pgp-inhibitor:	0.133
Pgp-substrate:	0.175
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.04
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	85.87776947021484%
Volume Distribution (VD):	0.791
Pgp-substrate:	12.026833534240723%

ADMET: Metabolism

CYP1A2-inhibitor:	0.954
CYP1A2-substrate:	0.804
CYP2C19-inhibitor:	0.436
CYP2C19-substrate:	0.136
CYP2C9-inhibitor:	0.397
CYP2C9-substrate:	0.498
CYP2D6-inhibitor:	0.402
CYP2D6-substrate:	0.814
CYP3A4-inhibitor:	0.079
CYP3A4-substrate:	0.305

ADMET: Excretion

Clearance (CL):	11.535
Half-life (T1/2):	0.255

ADMET: Toxicity

hERG Blockers:	0.276
Human Hepatotoxicity (H-HT):	0.244
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.709
Maximum Recommended Daily Dose:	0.887
Skin Sensitization:	0.24
Carcinogencity:	0.735
Eye Corrosion:	0.008
Eye Irritation:	0.8
Respiratory Toxicity:	0.733

Download Data

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

Natural Product: NPC131725

Natural Product ID:	NPC131725
*Common Name:**	(+)-Oxypeucedanin
IUPAC Name:	5-[[(2S)-3,3-dimethyloxiran-2-yl]methoxy]furo[3,2-g]chromen-7-one
Synonyms:	(+)-Oxypeucedanin
Standard InCHIKey:	NUCBCBCPICFGMZ-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C16H14O5/c1-16(2)14(21-16)8-19-12-7-15(17)20-13-6-11-9(3-4-18-11)5-10(12)13/h3-7,14H,8H2,1-2H3/t14-/m0/s1
SMILES:	O=c1cc(OC[C@@H]2OC2(C)C)c2c(o1)cc1c(c2)cco1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651087
PubChem CID:	53316971
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0000358] Furanocoumarins [CHEMONTID:0002569] Linear furanocoumarins [CHEMONTID:0000202] Psoralens

*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
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	DOI[10.5012/bkcs.2003.24.11.1699]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[12510838]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15646793]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21657081]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24813739]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25333853]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[27133212]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27444348]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31464439]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19017	Prangos pabularia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6190	Angelica archangelica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19017	Prangos pabularia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6190	Angelica archangelica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19017	Prangos pabularia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6190	Angelica archangelica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2953	Ostericum grosseserratum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19017	Prangos pabularia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2953	Ostericum grosseserratum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6190	Angelica archangelica	Species	Apiaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT67	Individual Protein	Cholinesterase	Equus caballus	IC50	=	64000.0	nM	PMID[541897]

☑ 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 NPC131725 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	451
0.1-0.2	1973
0.2-0.3	4972
0.3-0.4	11282
0.4-0.5	7237
0.5-0.6	5207
0.6-0.7	5679
0.7-0.8	5108
0.8-0.85	556
0.85-0.9	202
0.9-0.95	26
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9797	High Similarity	NPC295608
0.9797	High Similarity	NPC250769
0.9797	High Similarity	NPC278010
0.9459	High Similarity	NPC88445
0.9419	High Similarity	NPC173149
0.9419	High Similarity	NPC179015
0.9396	High Similarity	NPC191104
0.9392	High Similarity	NPC266743
0.9351	High Similarity	NPC14822
0.9324	High Similarity	NPC74539
0.9324	High Similarity	NPC304443
0.9315	High Similarity	NPC166858
0.9315	High Similarity	NPC51146
0.9286	High Similarity	NPC95472
0.9286	High Similarity	NPC169
0.9286	High Similarity	NPC49009
0.9286	High Similarity	NPC239270
0.9286	High Similarity	NPC303210
0.9189	High Similarity	NPC246903
0.9161	High Similarity	NPC243509
0.9156	High Similarity	NPC269495
0.9116	High Similarity	NPC254010
0.911	High Similarity	NPC262635
0.9103	High Similarity	NPC216092
0.9097	High Similarity	NPC33320
0.9079	High Similarity	NPC98028
0.9062	High Similarity	NPC144288
0.906	High Similarity	NPC208584
0.9054	High Similarity	NPC313036
0.9	High Similarity	NPC190572
0.8944	High Similarity	NPC51404
0.8933	High Similarity	NPC171656
0.8919	High Similarity	NPC470856
0.891	High Similarity	NPC270044
0.8889	High Similarity	NPC148423
0.8889	High Similarity	NPC135303
0.8889	High Similarity	NPC155882
0.8875	High Similarity	NPC67450
0.8875	High Similarity	NPC155264
0.8875	High Similarity	NPC193881
0.8875	High Similarity	NPC210460
0.8868	High Similarity	NPC179464
0.8867	High Similarity	NPC17262
0.8851	High Similarity	NPC136095
0.8846	High Similarity	NPC470625
0.8844	High Similarity	NPC253616
0.8824	High Similarity	NPC164299
0.8816	High Similarity	NPC198427
0.8808	High Similarity	NPC294365
0.8805	High Similarity	NPC234536
0.8805	High Similarity	NPC78612
0.8784	High Similarity	NPC36414
0.8782	High Similarity	NPC108937
0.8782	High Similarity	NPC279218
0.8776	High Similarity	NPC268081
0.8774	High Similarity	NPC38361
0.8774	High Similarity	NPC130015
0.8758	High Similarity	NPC306788
0.8742	High Similarity	NPC76657
0.8727	High Similarity	NPC325176
0.8726	High Similarity	NPC474738
0.8726	High Similarity	NPC19860
0.8726	High Similarity	NPC109967
0.8726	High Similarity	NPC78554
0.8726	High Similarity	NPC321372
0.8726	High Similarity	NPC475797
0.8726	High Similarity	NPC474609
0.8726	High Similarity	NPC129053
0.8726	High Similarity	NPC469936
0.8725	High Similarity	NPC472515
0.8718	High Similarity	NPC122365
0.8718	High Similarity	NPC41719
0.8716	High Similarity	NPC103001
0.871	High Similarity	NPC472407
0.8684	High Similarity	NPC470857
0.8679	High Similarity	NPC74749
0.8679	High Similarity	NPC43971
0.8679	High Similarity	NPC19554
0.8667	High Similarity	NPC53917
0.8667	High Similarity	NPC224165
0.8662	High Similarity	NPC233776
0.8654	High Similarity	NPC263676
0.8654	High Similarity	NPC327269
0.8654	High Similarity	NPC31627
0.8654	High Similarity	NPC476238
0.8654	High Similarity	NPC285623
0.8649	High Similarity	NPC472516
0.8649	High Similarity	NPC29638
0.8645	High Similarity	NPC180351
0.8645	High Similarity	NPC472406
0.8645	High Similarity	NPC472421
0.8642	High Similarity	NPC323137
0.8634	High Similarity	NPC15819
0.8614	High Similarity	NPC107244
0.8606	High Similarity	NPC233956
0.8606	High Similarity	NPC72455
0.86	High Similarity	NPC11566
0.86	High Similarity	NPC473209
0.8598	High Similarity	NPC120220
0.8591	High Similarity	NPC38153
0.859	High Similarity	NPC471675
0.859	High Similarity	NPC474744
0.859	High Similarity	NPC472423
0.859	High Similarity	NPC474772
0.859	High Similarity	NPC290671
0.859	High Similarity	NPC472580
0.8581	High Similarity	NPC296030
0.8581	High Similarity	NPC37208
0.8581	High Similarity	NPC221868
0.8581	High Similarity	NPC39929
0.858	High Similarity	NPC204088
0.858	High Similarity	NPC259007
0.858	High Similarity	NPC329215
0.8571	High Similarity	NPC130581
0.8571	High Similarity	NPC12148
0.8571	High Similarity	NPC218300
0.8571	High Similarity	NPC282335
0.8571	High Similarity	NPC247743
0.8562	High Similarity	NPC316535
0.8562	High Similarity	NPC470859
0.8553	High Similarity	NPC260902
0.8553	High Similarity	NPC296957
0.8545	High Similarity	NPC472584
0.8544	High Similarity	NPC474542
0.8543	High Similarity	NPC472409
0.8535	High Similarity	NPC477957
0.8535	High Similarity	NPC256141
0.8535	High Similarity	NPC473996
0.8526	High Similarity	NPC327059
0.8526	High Similarity	NPC470908
0.8526	High Similarity	NPC321387
0.8523	High Similarity	NPC161196
0.8523	High Similarity	NPC254741
0.8519	High Similarity	NPC65846
0.8516	High Similarity	NPC272194
0.8516	High Similarity	NPC168085
0.8516	High Similarity	NPC135325
0.8509	High Similarity	NPC264293
0.8509	High Similarity	NPC92589
0.8506	High Similarity	NPC210826
0.8506	High Similarity	NPC300267
0.8506	High Similarity	NPC51641
0.8503	High Similarity	NPC222036
0.8503	High Similarity	NPC229646
0.8503	High Similarity	NPC7526
0.85	High Similarity	NPC476350
0.85	High Similarity	NPC476349
0.85	High Similarity	NPC50430
0.8497	Intermediate Similarity	NPC302181
0.8497	Intermediate Similarity	NPC59522
0.8497	Intermediate Similarity	NPC225884
0.8491	Intermediate Similarity	NPC160015
0.8491	Intermediate Similarity	NPC247677
0.8487	Intermediate Similarity	NPC201820
0.8487	Intermediate Similarity	NPC22467
0.8487	Intermediate Similarity	NPC171870
0.8485	Intermediate Similarity	NPC281835
0.8471	Intermediate Similarity	NPC472636
0.8471	Intermediate Similarity	NPC156244
0.8471	Intermediate Similarity	NPC116604
0.8467	Intermediate Similarity	NPC259685
0.8462	Intermediate Similarity	NPC317492
0.8462	Intermediate Similarity	NPC37226
0.8462	Intermediate Similarity	NPC226644
0.8457	Intermediate Similarity	NPC219861
0.8456	Intermediate Similarity	NPC283331
0.8456	Intermediate Similarity	NPC46869
0.8452	Intermediate Similarity	NPC129650
0.8452	Intermediate Similarity	NPC202494
0.8452	Intermediate Similarity	NPC14875
0.8452	Intermediate Similarity	NPC471285
0.8447	Intermediate Similarity	NPC304839
0.8447	Intermediate Similarity	NPC115432
0.8447	Intermediate Similarity	NPC220582
0.8447	Intermediate Similarity	NPC260296
0.8446	Intermediate Similarity	NPC55149
0.8446	Intermediate Similarity	NPC292998
0.8446	Intermediate Similarity	NPC307412
0.8442	Intermediate Similarity	NPC297788
0.8442	Intermediate Similarity	NPC230943
0.8442	Intermediate Similarity	NPC179970
0.8442	Intermediate Similarity	NPC469953
0.8438	Intermediate Similarity	NPC65504
0.8435	Intermediate Similarity	NPC14248
0.8435	Intermediate Similarity	NPC175159
0.8431	Intermediate Similarity	NPC53192
0.8431	Intermediate Similarity	NPC147145
0.8428	Intermediate Similarity	NPC469934
0.8424	Intermediate Similarity	NPC41853
0.8418	Intermediate Similarity	NPC40033
0.8418	Intermediate Similarity	NPC67654
0.8418	Intermediate Similarity	NPC288534
0.8411	Intermediate Similarity	NPC17848
0.8408	Intermediate Similarity	NPC474735
0.8408	Intermediate Similarity	NPC189270
0.8408	Intermediate Similarity	NPC5840
0.8405	Intermediate Similarity	NPC472581
0.8405	Intermediate Similarity	NPC155640
0.8405	Intermediate Similarity	NPC91288
0.8397	Intermediate Similarity	NPC211811

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 NPC131725 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	1024
0.2-0.3	1879
0.3-0.4	2775
0.4-0.5	1878
0.5-0.6	857
0.6-0.7	241
0.7-0.8	101
0.8-0.85	9
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9324	High Similarity	NPD920	Approved
0.9315	High Similarity	NPD643	Clinical (unspecified phase)
0.9189	High Similarity	NPD642	Clinical (unspecified phase)
0.911	High Similarity	NPD1243	Approved
0.9097	High Similarity	NPD919	Approved
0.8523	High Similarity	NPD2796	Approved
0.8509	High Similarity	NPD1247	Approved
0.8481	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD6801	Discontinued
0.8377	Intermediate Similarity	NPD6799	Approved
0.8323	Intermediate Similarity	NPD7075	Discontinued
0.821	Intermediate Similarity	NPD3749	Approved
0.8176	Intermediate Similarity	NPD6599	Discontinued
0.8166	Intermediate Similarity	NPD6559	Discontinued
0.8137	Intermediate Similarity	NPD7819	Suspended
0.8125	Intermediate Similarity	NPD7411	Suspended
0.811	Intermediate Similarity	NPD5494	Approved
0.8089	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD4380	Phase 2
0.8052	Intermediate Similarity	NPD1549	Phase 2
0.7987	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3817	Phase 2
0.7975	Intermediate Similarity	NPD5401	Approved
0.7974	Intermediate Similarity	NPD3748	Approved
0.7974	Intermediate Similarity	NPD1510	Phase 2
0.7922	Intermediate Similarity	NPD1551	Phase 2
0.7914	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD5403	Approved
0.7857	Intermediate Similarity	NPD3926	Phase 2
0.7853	Intermediate Similarity	NPD1934	Approved
0.7829	Intermediate Similarity	NPD1240	Approved
0.7818	Intermediate Similarity	NPD3882	Suspended
0.7818	Intermediate Similarity	NPD7768	Phase 2
0.7811	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD6832	Phase 2
0.7771	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1607	Approved
0.7722	Intermediate Similarity	NPD3750	Approved
0.7719	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD3818	Discontinued
0.7707	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD5844	Phase 1
0.7658	Intermediate Similarity	NPD2800	Approved
0.7654	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5402	Approved
0.7643	Intermediate Similarity	NPD2344	Approved
0.764	Intermediate Similarity	NPD2533	Approved
0.764	Intermediate Similarity	NPD2532	Approved
0.764	Intermediate Similarity	NPD2534	Approved
0.7628	Intermediate Similarity	NPD2799	Discontinued
0.761	Intermediate Similarity	NPD4628	Phase 3
0.761	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD2801	Approved
0.7582	Intermediate Similarity	NPD2313	Discontinued
0.7578	Intermediate Similarity	NPD1511	Approved
0.7548	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5953	Discontinued
0.7485	Intermediate Similarity	NPD1512	Approved
0.7485	Intermediate Similarity	NPD6808	Phase 2
0.7485	Intermediate Similarity	NPD6232	Discontinued
0.7484	Intermediate Similarity	NPD4307	Phase 2
0.7468	Intermediate Similarity	NPD1296	Phase 2
0.7468	Intermediate Similarity	NPD2935	Discontinued
0.7457	Intermediate Similarity	NPD7473	Discontinued
0.7453	Intermediate Similarity	NPD2309	Approved
0.745	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1933	Approved
0.7434	Intermediate Similarity	NPD1019	Discontinued
0.743	Intermediate Similarity	NPD8434	Phase 2
0.7427	Intermediate Similarity	NPD6959	Discontinued
0.7405	Intermediate Similarity	NPD7033	Discontinued
0.74	Intermediate Similarity	NPD9717	Approved
0.7399	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6166	Phase 2
0.7371	Intermediate Similarity	NPD7054	Approved
0.7371	Intermediate Similarity	NPD7286	Phase 2
0.7368	Intermediate Similarity	NPD3267	Approved
0.7368	Intermediate Similarity	NPD1203	Approved
0.7368	Intermediate Similarity	NPD3266	Approved
0.7349	Intermediate Similarity	NPD3226	Approved
0.7346	Intermediate Similarity	NPD3887	Approved
0.733	Intermediate Similarity	NPD7472	Approved
0.733	Intermediate Similarity	NPD7074	Phase 3
0.7329	Intermediate Similarity	NPD2654	Approved
0.7325	Intermediate Similarity	NPD5124	Phase 1
0.7325	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1471	Phase 3
0.731	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4308	Phase 3
0.7288	Intermediate Similarity	NPD6797	Phase 2
0.7253	Intermediate Similarity	NPD4287	Approved
0.7247	Intermediate Similarity	NPD7251	Discontinued
0.7219	Intermediate Similarity	NPD422	Phase 1
0.7219	Intermediate Similarity	NPD6280	Approved
0.7219	Intermediate Similarity	NPD6279	Approved
0.7215	Intermediate Similarity	NPD447	Suspended
0.7207	Intermediate Similarity	NPD7808	Phase 3
0.7205	Intermediate Similarity	NPD2353	Approved
0.7205	Intermediate Similarity	NPD2346	Discontinued
0.7205	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2403	Approved
0.7176	Intermediate Similarity	NPD1465	Phase 2
0.717	Intermediate Similarity	NPD6651	Approved
0.716	Intermediate Similarity	NPD5889	Approved
0.716	Intermediate Similarity	NPD5890	Approved
0.7134	Intermediate Similarity	NPD3268	Approved
0.7119	Intermediate Similarity	NPD3751	Discontinued
0.7115	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6355	Discontinued
0.7101	Intermediate Similarity	NPD6585	Discontinued
0.7097	Intermediate Similarity	NPD2798	Approved
0.7095	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD17	Approved
0.7086	Intermediate Similarity	NPD5711	Approved
0.7086	Intermediate Similarity	NPD5710	Approved
0.7086	Intermediate Similarity	NPD7229	Phase 3
0.7075	Intermediate Similarity	NPD1241	Discontinued
0.7073	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7458	Discontinued
0.7039	Intermediate Similarity	NPD1729	Discontinued
0.7037	Intermediate Similarity	NPD8285	Discontinued
0.7035	Intermediate Similarity	NPD4288	Approved
0.7032	Intermediate Similarity	NPD2797	Approved
0.703	Intermediate Similarity	NPD2354	Approved
0.7029	Intermediate Similarity	NPD7199	Phase 2
0.7025	Intermediate Similarity	NPD411	Approved
0.7025	Intermediate Similarity	NPD6798	Discontinued
0.7012	Intermediate Similarity	NPD1652	Phase 2
0.7006	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD230	Phase 1
0.6989	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD3787	Discontinued
0.6977	Remote Similarity	NPD5760	Phase 2
0.6977	Remote Similarity	NPD5761	Phase 2
0.6968	Remote Similarity	NPD3225	Approved
0.6964	Remote Similarity	NPD5049	Phase 3
0.6954	Remote Similarity	NPD9545	Approved
0.6951	Remote Similarity	NPD2424	Discontinued
0.6949	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5242	Approved
0.6948	Remote Similarity	NPD1608	Approved
0.6948	Remote Similarity	NPD3972	Approved
0.6946	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD943	Approved
0.6936	Remote Similarity	NPD2296	Approved
0.6936	Remote Similarity	NPD5353	Approved
0.6933	Remote Similarity	NPD2438	Suspended
0.6918	Remote Similarity	NPD3764	Approved
0.689	Remote Similarity	NPD6002	Phase 3
0.689	Remote Similarity	NPD6005	Phase 3
0.689	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6004	Phase 3
0.6882	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD8455	Phase 2
0.6878	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4361	Phase 2
0.6872	Remote Similarity	NPD7584	Approved
0.6871	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6764	Approved
0.6868	Remote Similarity	NPD6765	Approved
0.6864	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6273	Approved
0.6859	Remote Similarity	NPD1876	Approved
0.6825	Remote Similarity	NPD4363	Phase 3
0.6825	Remote Similarity	NPD4360	Phase 2
0.6821	Remote Similarity	NPD37	Approved
0.6821	Remote Similarity	NPD9493	Approved
0.6816	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1164	Approved
0.6813	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD4662	Approved
0.6805	Remote Similarity	NPD4661	Approved
0.68	Remote Similarity	NPD4965	Approved
0.68	Remote Similarity	NPD4967	Phase 2
0.68	Remote Similarity	NPD4966	Approved
0.6793	Remote Similarity	NPD8313	Approved
0.6793	Remote Similarity	NPD8312	Approved
0.6786	Remote Similarity	NPD7583	Approved
0.6774	Remote Similarity	NPD1281	Approved
0.677	Remote Similarity	NPD6233	Phase 2
0.6766	Remote Similarity	NPD7003	Approved
0.6763	Remote Similarity	NPD6386	Approved
0.6763	Remote Similarity	NPD6385	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