NPASS Compound

Structure

CID176005 OpenBabel06191715552D 39 43 0 0 1 0 0 0 0 0999 V2000 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8538 3.3750 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 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6356 2.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0246 2.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8065 3.3750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.0860 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 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 12 1 0 0 0 0 5 35 1 0 0 0 0 6 36 1 0 0 0 0 7 11 1 0 0 0 0 7 15 2 0 0 0 0 8 13 1 0 0 0 0 8 17 1 0 0 0 0 9 14 1 0 0 0 0 9 18 1 0 0 0 0 10 29 1 0 0 0 0 11 1 1 1 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 12 23 2 0 0 0 0 13 28 1 6 0 0 0 14 27 1 1 0 0 0 15 25 1 0 0 0 0 15 35 1 0 0 0 0 16 10 1 6 0 0 0 16 19 1 0 0 0 0 16 37 1 0 0 0 0 17 27 1 1 0 0 0 17 38 1 0 0 0 0 18 38 1 0 0 0 0 18 39 1 1 0 0 0 19 20 1 0 0 0 0 19 30 1 1 0 0 0 20 21 1 0 0 0 0 20 31 1 6 0 0 0 21 26 1 0 0 0 0 21 32 1 1 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 22 33 2 0 0 0 0 23 36 1 0 0 0 0 24 27 1 6 0 0 0 24 28 1 0 0 0 0 25 28 1 0 0 0 0 25 34 2 0 0 0 0 26 37 1 0 0 0 0 26 39 1 6 0 0 0 27 3 1 6 0 0 0 28 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	552.26
Volume:	536.208
LogP:	1.036
LogD:	0.735
LogS:	-3.649
# Rotatable Bonds:	5
TPSA:	161.21
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.346
Synthetic Accessibility Score:	5.659
Fsp3:	0.786
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.343
MDCK Permeability:	0.00012034581595798954
Pgp-inhibitor:	0.997
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.677
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.885

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	39.04534149169922%
Volume Distribution (VD):	1.455
Pgp-substrate:	31.98401641845703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.705
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.089
CYP3A4-substrate:	0.528

ADMET: Excretion

Clearance (CL):	2.265
Half-life (T1/2):	0.313

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.335
Drug-inuced Liver Injury (DILI):	0.724
AMES Toxicity:	0.755
Rat Oral Acute Toxicity:	0.406
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.153
Carcinogencity:	0.065
Eye Corrosion:	0.004
Eye Irritation:	0.01
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC176005

Natural Product ID:	NPC176005
*Common Name:**	Picrasinoside B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WBJUWMYAOGSXPY-NBTOIYHCSA-N
Standard InCHI:	InChI=1S/C28H40O11/c1-11-7-15(35-5)25(34)28(4)13(11)8-17-27(3)14(12(2)23(36-6)22(33)24(27)28)9-18(38-17)39-26-21(32)20(31)19(30)16(10-29)37-26/h7,11,13-14,16-21,24,26,29-32H,8-10H2,1-6H3/t11-,13+,14+,16-,17-,18+,19-,20+,21-,24+,26+,27-,28+/m1/s1
SMILES:	C[C@@H]1C=C(C(=O)[C@@]2(C)[C@H]1C[C@@H]1[C@@]3(C)[C@@H](C[C@@H](O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(=C(C(=O)[C@H]23)OC)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451890
PubChem CID:	44576016
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO1268	Picrasma ailanthoides	Species	Simaroubaceae	Eukaryota	stem wood	n.a.	n.a.	PMID[1955884]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19586051]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	stems	n.a.	n.a.	PMID[20095629]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25506718]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27494664]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30917277]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1268	Picrasma ailanthoides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	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
ED50	6
Others	4

Activity Type	# Activity
Cell Line	9
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	<=	4.0	ug ml-1	PMID[459979]
NPT672	Cell Line	TE-671	Homo sapiens	ED50	<=	4.0	ug ml-1	PMID[459979]
NPT81	Cell Line	A549	Homo sapiens	ED50	<=	4.0	ug ml-1	PMID[459979]
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	<=	4.0	ug ml-1	PMID[459979]
NPT168	Cell Line	P388	Mus musculus	ED50	<=	4.0	ug ml-1	PMID[459979]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	82.2	%	PMID[459980]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	7.43	%	PMID[459980]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	8.55	%	PMID[459980]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	1.86	%	PMID[459980]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	<=	4.0	ug ml-1	PMID[459979]

☑ 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 NPC176005 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	281
0.1-0.2	1797
0.2-0.3	5083
0.3-0.4	8448
0.4-0.5	11866
0.5-0.6	8505
0.6-0.7	4635
0.7-0.8	1709
0.8-0.85	326
0.85-0.9	41
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC279143
0.9375	High Similarity	NPC473920
0.9375	High Similarity	NPC127530
0.9211	High Similarity	NPC275675
0.9052	High Similarity	NPC227397
0.8991	High Similarity	NPC272576
0.886	High Similarity	NPC309433
0.8814	High Similarity	NPC7850
0.8814	High Similarity	NPC6615
0.8803	High Similarity	NPC471965
0.875	High Similarity	NPC475636
0.875	High Similarity	NPC295220
0.8729	High Similarity	NPC202666
0.8729	High Similarity	NPC471964
0.8729	High Similarity	NPC14617
0.8729	High Similarity	NPC471961
0.8729	High Similarity	NPC262199
0.8718	High Similarity	NPC187950
0.8718	High Similarity	NPC42675
0.8718	High Similarity	NPC278163
0.8678	High Similarity	NPC54614
0.8678	High Similarity	NPC309096
0.8655	High Similarity	NPC177820
0.8655	High Similarity	NPC471962
0.8655	High Similarity	NPC247315
0.8655	High Similarity	NPC277191
0.8655	High Similarity	NPC190846
0.8655	High Similarity	NPC471963
0.8655	High Similarity	NPC30188
0.8609	High Similarity	NPC31797
0.8596	High Similarity	NPC62696
0.8596	High Similarity	NPC293038
0.8595	High Similarity	NPC293623
0.8595	High Similarity	NPC69273
0.8595	High Similarity	NPC168899
0.8583	High Similarity	NPC87662
0.8583	High Similarity	NPC285091
0.8571	High Similarity	NPC27814
0.8571	High Similarity	NPC1980
0.8571	High Similarity	NPC238005
0.8571	High Similarity	NPC141196
0.8547	High Similarity	NPC472949
0.8547	High Similarity	NPC309780
0.8547	High Similarity	NPC180550
0.8547	High Similarity	NPC6377
0.8547	High Similarity	NPC114441
0.8547	High Similarity	NPC35405
0.8547	High Similarity	NPC208381
0.8547	High Similarity	NPC469945
0.8547	High Similarity	NPC11551
0.8547	High Similarity	NPC475171
0.8547	High Similarity	NPC473884
0.8547	High Similarity	NPC192791
0.8547	High Similarity	NPC214484
0.8547	High Similarity	NPC39211
0.8547	High Similarity	NPC157868
0.8522	High Similarity	NPC102088
0.85	High Similarity	NPC469841
0.85	High Similarity	NPC469842
0.8487	Intermediate Similarity	NPC162574
0.8487	Intermediate Similarity	NPC275343
0.8487	Intermediate Similarity	NPC216866
0.8462	Intermediate Similarity	NPC286347
0.8462	Intermediate Similarity	NPC109588
0.8455	Intermediate Similarity	NPC241008
0.843	Intermediate Similarity	NPC93368
0.843	Intermediate Similarity	NPC198714
0.8413	Intermediate Similarity	NPC190065
0.8413	Intermediate Similarity	NPC471089
0.8413	Intermediate Similarity	NPC141215
0.8403	Intermediate Similarity	NPC412
0.8403	Intermediate Similarity	NPC223301
0.8403	Intermediate Similarity	NPC131841
0.8403	Intermediate Similarity	NPC258789
0.8403	Intermediate Similarity	NPC75417
0.8403	Intermediate Similarity	NPC11242
0.8403	Intermediate Similarity	NPC297263
0.8403	Intermediate Similarity	NPC258815
0.8403	Intermediate Similarity	NPC47567
0.8403	Intermediate Similarity	NPC169727
0.8403	Intermediate Similarity	NPC86222
0.8403	Intermediate Similarity	NPC301449
0.8403	Intermediate Similarity	NPC104372
0.8403	Intermediate Similarity	NPC194310
0.8403	Intermediate Similarity	NPC64715
0.8403	Intermediate Similarity	NPC171544
0.8403	Intermediate Similarity	NPC242840
0.8403	Intermediate Similarity	NPC222580
0.8403	Intermediate Similarity	NPC241310
0.8403	Intermediate Similarity	NPC159309
0.8403	Intermediate Similarity	NPC31193
0.8403	Intermediate Similarity	NPC31838
0.8403	Intermediate Similarity	NPC114484
0.8403	Intermediate Similarity	NPC22956
0.8403	Intermediate Similarity	NPC62725
0.839	Intermediate Similarity	NPC473401
0.8376	Intermediate Similarity	NPC224121
0.8374	Intermediate Similarity	NPC477196
0.8362	Intermediate Similarity	NPC18547
0.8362	Intermediate Similarity	NPC474906
0.8361	Intermediate Similarity	NPC152091
0.8348	Intermediate Similarity	NPC471967
0.8347	Intermediate Similarity	NPC130229
0.8347	Intermediate Similarity	NPC475194
0.8346	Intermediate Similarity	NPC140045
0.8346	Intermediate Similarity	NPC596
0.8346	Intermediate Similarity	NPC295885
0.8333	Intermediate Similarity	NPC78046
0.8333	Intermediate Similarity	NPC4749
0.8333	Intermediate Similarity	NPC80986
0.8333	Intermediate Similarity	NPC187290
0.8333	Intermediate Similarity	NPC40775
0.8333	Intermediate Similarity	NPC21691
0.8333	Intermediate Similarity	NPC236870
0.8333	Intermediate Similarity	NPC107966
0.8333	Intermediate Similarity	NPC249848
0.8333	Intermediate Similarity	NPC262813
0.8333	Intermediate Similarity	NPC475591
0.8333	Intermediate Similarity	NPC235438
0.8333	Intermediate Similarity	NPC213952
0.8333	Intermediate Similarity	NPC269095
0.8333	Intermediate Similarity	NPC10607
0.8319	Intermediate Similarity	NPC236657
0.8319	Intermediate Similarity	NPC118440
0.8319	Intermediate Similarity	NPC294112
0.8306	Intermediate Similarity	NPC477197
0.8293	Intermediate Similarity	NPC477193
0.8293	Intermediate Similarity	NPC477191
0.8293	Intermediate Similarity	NPC477194
0.8293	Intermediate Similarity	NPC477192
0.8291	Intermediate Similarity	NPC235539
0.8291	Intermediate Similarity	NPC134869
0.8291	Intermediate Similarity	NPC152199
0.8279	Intermediate Similarity	NPC469947
0.8279	Intermediate Similarity	NPC181066
0.8268	Intermediate Similarity	NPC251998
0.8264	Intermediate Similarity	NPC2370
0.8264	Intermediate Similarity	NPC257211
0.8264	Intermediate Similarity	NPC283417
0.8264	Intermediate Similarity	NPC200049
0.8264	Intermediate Similarity	NPC44716
0.8264	Intermediate Similarity	NPC235405
0.8264	Intermediate Similarity	NPC30735
0.8264	Intermediate Similarity	NPC281148
0.8264	Intermediate Similarity	NPC258617
0.8264	Intermediate Similarity	NPC302543
0.8257	Intermediate Similarity	NPC70733
0.8257	Intermediate Similarity	NPC56071
0.825	Intermediate Similarity	NPC302887
0.825	Intermediate Similarity	NPC202051
0.825	Intermediate Similarity	NPC187618
0.8246	Intermediate Similarity	NPC137917
0.824	Intermediate Similarity	NPC477195
0.824	Intermediate Similarity	NPC476776
0.8235	Intermediate Similarity	NPC258592
0.8235	Intermediate Similarity	NPC319570
0.8235	Intermediate Similarity	NPC178548
0.8226	Intermediate Similarity	NPC97918
0.8226	Intermediate Similarity	NPC11577
0.8226	Intermediate Similarity	NPC244296
0.8226	Intermediate Similarity	NPC477076
0.8226	Intermediate Similarity	NPC280029
0.8226	Intermediate Similarity	NPC477077
0.8226	Intermediate Similarity	NPC470518
0.8226	Intermediate Similarity	NPC141600
0.8226	Intermediate Similarity	NPC88311
0.8226	Intermediate Similarity	NPC9470
0.8226	Intermediate Similarity	NPC47995
0.8226	Intermediate Similarity	NPC82380
0.8226	Intermediate Similarity	NPC107536
0.8226	Intermediate Similarity	NPC115656
0.8226	Intermediate Similarity	NPC472267
0.8226	Intermediate Similarity	NPC273878
0.8226	Intermediate Similarity	NPC252289
0.8226	Intermediate Similarity	NPC269484
0.8226	Intermediate Similarity	NPC265841
0.8226	Intermediate Similarity	NPC1314
0.8226	Intermediate Similarity	NPC305793
0.8226	Intermediate Similarity	NPC252657
0.8226	Intermediate Similarity	NPC470913
0.8226	Intermediate Similarity	NPC477079
0.822	Intermediate Similarity	NPC477252
0.8205	Intermediate Similarity	NPC475633
0.8205	Intermediate Similarity	NPC474557
0.8205	Intermediate Similarity	NPC165439
0.8197	Intermediate Similarity	NPC33068
0.8197	Intermediate Similarity	NPC160452
0.8197	Intermediate Similarity	NPC470477
0.819	Intermediate Similarity	NPC195132
0.819	Intermediate Similarity	NPC256798
0.819	Intermediate Similarity	NPC128925
0.819	Intermediate Similarity	NPC11252
0.819	Intermediate Similarity	NPC161434
0.819	Intermediate Similarity	NPC289312
0.8182	Intermediate Similarity	NPC313110
0.8182	Intermediate Similarity	NPC475431
0.8182	Intermediate Similarity	NPC131469
0.8182	Intermediate Similarity	NPC131824
0.8182	Intermediate Similarity	NPC104861
0.8175	Intermediate Similarity	NPC476779

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 NPC176005 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	2101
0.2-0.3	3863
0.3-0.4	1883
0.4-0.5	573
0.5-0.6	273
0.6-0.7	145
0.7-0.8	44
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8729	High Similarity	NPD8328	Phase 3
0.8407	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8376	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7913	Intermediate Similarity	NPD6412	Phase 2
0.7886	Intermediate Similarity	NPD6370	Approved
0.7724	Intermediate Similarity	NPD6054	Approved
0.7717	Intermediate Similarity	NPD7736	Approved
0.7583	Intermediate Similarity	NPD6882	Approved
0.7581	Intermediate Similarity	NPD6059	Approved
0.7542	Intermediate Similarity	NPD6686	Approved
0.752	Intermediate Similarity	NPD6015	Approved
0.752	Intermediate Similarity	NPD6016	Approved
0.75	Intermediate Similarity	NPD6650	Approved
0.75	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD8293	Discontinued
0.748	Intermediate Similarity	NPD6009	Approved
0.748	Intermediate Similarity	NPD7492	Approved
0.7479	Intermediate Similarity	NPD6373	Approved
0.7479	Intermediate Similarity	NPD6372	Approved
0.746	Intermediate Similarity	NPD5988	Approved
0.744	Intermediate Similarity	NPD6319	Approved
0.7438	Intermediate Similarity	NPD8297	Approved
0.7422	Intermediate Similarity	NPD6616	Approved
0.7422	Intermediate Similarity	NPD7507	Approved
0.7364	Intermediate Similarity	NPD7078	Approved
0.7252	Intermediate Similarity	NPD7319	Approved
0.725	Intermediate Similarity	NPD6899	Approved
0.725	Intermediate Similarity	NPD6881	Approved
0.7244	Intermediate Similarity	NPD7503	Approved
0.7236	Intermediate Similarity	NPD4632	Approved
0.7227	Intermediate Similarity	NPD5739	Approved
0.7227	Intermediate Similarity	NPD7128	Approved
0.7227	Intermediate Similarity	NPD6402	Approved
0.7227	Intermediate Similarity	NPD6675	Approved
0.7217	Intermediate Similarity	NPD7902	Approved
0.7167	Intermediate Similarity	NPD5697	Approved
0.7131	Intermediate Similarity	NPD6883	Approved
0.7131	Intermediate Similarity	NPD7290	Approved
0.7131	Intermediate Similarity	NPD7102	Approved
0.7109	Intermediate Similarity	NPD8513	Phase 3
0.7109	Intermediate Similarity	NPD8517	Approved
0.7109	Intermediate Similarity	NPD8516	Approved
0.7109	Intermediate Similarity	NPD8515	Approved
0.7107	Intermediate Similarity	NPD7320	Approved
0.7107	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD8133	Approved
0.7073	Intermediate Similarity	NPD8130	Phase 1
0.7073	Intermediate Similarity	NPD6847	Approved
0.7073	Intermediate Similarity	NPD6617	Approved
0.7073	Intermediate Similarity	NPD6869	Approved
0.7049	Intermediate Similarity	NPD6013	Approved
0.7049	Intermediate Similarity	NPD6014	Approved
0.7049	Intermediate Similarity	NPD6012	Approved
0.7045	Intermediate Similarity	NPD6033	Approved
0.7031	Intermediate Similarity	NPD8377	Approved
0.7031	Intermediate Similarity	NPD8294	Approved
0.7025	Intermediate Similarity	NPD5701	Approved
0.7	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7604	Phase 2
0.6992	Remote Similarity	NPD4634	Approved
0.6983	Remote Similarity	NPD4697	Phase 3
0.6977	Remote Similarity	NPD5983	Phase 2
0.6977	Remote Similarity	NPD8380	Approved
0.6977	Remote Similarity	NPD8379	Approved
0.6977	Remote Similarity	NPD8335	Approved
0.6977	Remote Similarity	NPD8296	Approved
0.6977	Remote Similarity	NPD8378	Approved
0.6977	Remote Similarity	NPD8033	Approved
0.6967	Remote Similarity	NPD6011	Approved
0.6957	Remote Similarity	NPD7900	Approved
0.6957	Remote Similarity	NPD7748	Approved
0.6957	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5285	Approved
0.6949	Remote Similarity	NPD4696	Approved
0.6949	Remote Similarity	NPD5286	Approved
0.693	Remote Similarity	NPD7515	Phase 2
0.6923	Remote Similarity	NPD4755	Approved
0.6894	Remote Similarity	NPD6336	Discontinued
0.6875	Remote Similarity	NPD7328	Approved
0.6875	Remote Similarity	NPD7327	Approved
0.687	Remote Similarity	NPD6067	Discontinued
0.6838	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5221	Approved
0.6838	Remote Similarity	NPD5222	Approved
0.6833	Remote Similarity	NPD5224	Approved
0.6833	Remote Similarity	NPD5226	Approved
0.6833	Remote Similarity	NPD4633	Approved
0.6833	Remote Similarity	NPD5225	Approved
0.6833	Remote Similarity	NPD5211	Phase 2
0.6822	Remote Similarity	NPD7516	Approved
0.6807	Remote Similarity	NPD4700	Approved
0.68	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6079	Approved
0.678	Remote Similarity	NPD5173	Approved
0.6777	Remote Similarity	NPD5175	Approved
0.6777	Remote Similarity	NPD5174	Approved
0.6754	Remote Similarity	NPD5328	Approved
0.675	Remote Similarity	NPD5223	Approved
0.6721	Remote Similarity	NPD5141	Approved
0.672	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6274	Approved
0.6694	Remote Similarity	NPD4730	Approved
0.6694	Remote Similarity	NPD4729	Approved
0.6692	Remote Similarity	NPD7100	Approved
0.6692	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD8080	Discontinued
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6642	Remote Similarity	NPD7260	Phase 2
0.664	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6083	Phase 2
0.6639	Remote Similarity	NPD6084	Phase 2
0.6637	Remote Similarity	NPD3618	Phase 1
0.6615	Remote Similarity	NPD6335	Approved
0.661	Remote Similarity	NPD5695	Phase 3
0.6609	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6921	Approved
0.6589	Remote Similarity	NPD6868	Approved
0.6587	Remote Similarity	NPD5251	Approved
0.6587	Remote Similarity	NPD5248	Approved
0.6587	Remote Similarity	NPD5249	Phase 3
0.6587	Remote Similarity	NPD5250	Approved
0.6587	Remote Similarity	NPD5247	Approved
0.6581	Remote Similarity	NPD6399	Phase 3
0.6579	Remote Similarity	NPD3573	Approved
0.656	Remote Similarity	NPD5128	Approved
0.6538	Remote Similarity	NPD6317	Approved
0.6532	Remote Similarity	NPD6008	Approved
0.6525	Remote Similarity	NPD5282	Discontinued
0.6504	Remote Similarity	NPD4754	Approved
0.6496	Remote Similarity	NPD6411	Approved
0.6489	Remote Similarity	NPD6313	Approved
0.6489	Remote Similarity	NPD6314	Approved
0.648	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6845	Suspended
0.6466	Remote Similarity	NPD6908	Approved
0.6466	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6909	Approved
0.6449	Remote Similarity	NPD5956	Approved
0.6446	Remote Similarity	NPD5696	Approved
0.6446	Remote Similarity	NPD7638	Approved
0.6406	Remote Similarity	NPD5215	Approved
0.6406	Remote Similarity	NPD5216	Approved
0.6406	Remote Similarity	NPD5217	Approved
0.6396	Remote Similarity	NPD4695	Discontinued
0.6393	Remote Similarity	NPD7639	Approved
0.6393	Remote Similarity	NPD7640	Approved
0.6379	Remote Similarity	NPD5737	Approved
0.6379	Remote Similarity	NPD6672	Approved
0.6372	Remote Similarity	NPD6110	Phase 1
0.6364	Remote Similarity	NPD7641	Discontinued
0.635	Remote Similarity	NPD8074	Phase 3
0.6348	Remote Similarity	NPD5279	Phase 3
0.6343	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4629	Approved
0.6333	Remote Similarity	NPD5210	Approved
0.6328	Remote Similarity	NPD5135	Approved
0.6328	Remote Similarity	NPD5169	Approved
0.6328	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6101	Approved
0.6325	Remote Similarity	NPD4753	Phase 2
0.6311	Remote Similarity	NPD4225	Approved
0.6311	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4202	Approved
0.6299	Remote Similarity	NPD5168	Approved
0.6279	Remote Similarity	NPD5127	Approved
0.6271	Remote Similarity	NPD46	Approved
0.6271	Remote Similarity	NPD6698	Approved
0.6231	Remote Similarity	NPD6053	Discontinued
0.6228	Remote Similarity	NPD3669	Approved
0.6228	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD8035	Phase 2
0.6218	Remote Similarity	NPD8034	Phase 2
0.6214	Remote Similarity	NPD6914	Discontinued
0.6207	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD8336	Approved
0.6187	Remote Similarity	NPD8337	Approved
0.6181	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD3666	Approved
0.6174	Remote Similarity	NPD3133	Approved
0.6174	Remote Similarity	NPD4786	Approved
0.6174	Remote Similarity	NPD3665	Phase 1
0.6167	Remote Similarity	NPD5779	Approved
0.6167	Remote Similarity	NPD5778	Approved
0.6167	Remote Similarity	NPD8171	Discontinued
0.6165	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7645	Phase 2
0.6148	Remote Similarity	NPD7614	Phase 1
0.614	Remote Similarity	NPD3667	Approved
0.6136	Remote Similarity	NPD5167	Approved
0.6102	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD6050	Approved
0.6071	Remote Similarity	NPD3617	Approved
0.6068	Remote Similarity	NPD7146	Approved
0.6068	Remote Similarity	NPD5330	Approved
0.6068	Remote Similarity	NPD7521	Approved
0.6068	Remote Similarity	NPD6409	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