NPASS Compound

Structure

CID240509 OpenBabel06191716042D 27 33 0 0 1 0 0 0 0 0999 V2000 -0.8475 3.4185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 3.4176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8458 1.4661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6935 -0.9759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 -0.4883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6919 1.9552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2305 0.4907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6929 2.9298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5395 -0.4874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5390 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8453 2.4428 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6918 0.9755 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8458 0.4880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3861 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 2.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 0.4889 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6924 0.9774 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6923 1.9534 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0008 1.9543 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9765 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3870 -1.9750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8477 3.4419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6929 0.0007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2310 -0.4865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0008 2.9313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5389 1.4640 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 8 1 0 0 0 0 2 8 1 0 0 0 0 3 16 1 0 0 0 0 4 5 1 0 0 0 0 4 9 1 0 0 0 0 5 16 1 0 0 0 0 6 11 1 0 0 0 0 6 17 1 0 0 0 0 7 10 1 0 0 0 0 7 24 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 1 0 0 0 11 25 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 1 0 0 0 12 26 1 0 0 0 0 13 20 1 1 0 0 0 13 27 1 0 0 0 0 14 21 2 0 0 0 0 14 24 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 15 22 2 0 0 0 0 16 17 1 6 0 0 0 17 23 1 6 0 0 0 18 8 1 1 0 0 0 18 26 1 0 0 0 0 19 20 1 1 0 0 0 19 25 1 0 0 0 0 20 16 1 6 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.14
Volume:	348.203
LogP:	2.29
LogD:	2.108
LogS:	-4.359
# Rotatable Bonds:	1
TPSA:	108.26
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.711
Synthetic Accessibility Score:	6.469
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.696
MDCK Permeability:	3.013234891113825e-05
Pgp-inhibitor:	0.037
Pgp-substrate:	0.874
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.091
30% Bioavailability (F30%):	0.667

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.958
Plasma Protein Binding (PPB):	87.61568450927734%
Volume Distribution (VD):	1.123
Pgp-substrate:	19.930810928344727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.99
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.278
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.203
CYP3A4-inhibitor:	0.039
CYP3A4-substrate:	0.805

ADMET: Excretion

Clearance (CL):	15.694
Half-life (T1/2):	0.084

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.525
Drug-inuced Liver Injury (DILI):	0.641
AMES Toxicity:	0.901
Rat Oral Acute Toxicity:	0.979
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.903
Carcinogencity:	0.99
Eye Corrosion:	0.009
Eye Irritation:	0.032
Respiratory Toxicity:	0.995

Download Data

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

Natural Product: NPC240509

Natural Product ID:	NPC240509
*Common Name:**	SVWZPKRMGJFEFO-COQXYOOISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SVWZPKRMGJFEFO-COQXYOOISA-N
Standard InCHI:	InChI=1S/C20H22O7/c1-8(2)18-12(26-18)13-20(27-13)16(3)5-4-9-10(7-24-14(9)21)17(16,23)6-11-19(20,25-11)15(18)22/h8,11-13,23H,4-7H2,1-3H3/t11-,12-,13-,16-,17+,18-,19+,20+/m0/s1
SMILES:	O=C1OCC2=C1CC[C@]1([C@@]2(O)C[C@H]2[C@@]3([C@@]41O[C@H]4[C@@H]1O[C@@]1(C3=O)C(C)C)O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3358843
PubChem CID:	10384773
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(90)85349-K]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1186/1471-2202-6-1]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579865]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[10716597]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374948]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11561442]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12579877]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[16864458]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[16989518]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17250858]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17265278]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18554602]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[18996177]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	root	n.a.	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21514608]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	dried roots	purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China)	n.a.	PMID[22148431]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[23268606]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23852638]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24549173]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24963543]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25237706]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[2534610]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[2816380]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29355322]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31556299]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7102323]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7304185]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699928]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8722541]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT380	Cell Line	U-251	Homo sapiens	IC50	=	1031.0	nM	PMID[564877]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	377.0	nM	PMID[564877]

☑ 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 NPC240509 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	302
0.1-0.2	1943
0.2-0.3	5262
0.3-0.4	8054
0.4-0.5	13123
0.5-0.6	8076
0.6-0.7	4692
0.7-0.8	1159
0.8-0.85	76
0.85-0.9	7
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC33360
0.9182	High Similarity	NPC42658
0.8909	High Similarity	NPC299590
0.8696	High Similarity	NPC58662
0.8583	High Similarity	NPC225049
0.8534	High Similarity	NPC469684
0.85	High Similarity	NPC476729
0.8487	Intermediate Similarity	NPC312833
0.8475	Intermediate Similarity	NPC268530
0.8475	Intermediate Similarity	NPC154491
0.8462	Intermediate Similarity	NPC251310
0.8443	Intermediate Similarity	NPC476859
0.8421	Intermediate Similarity	NPC469655
0.8421	Intermediate Similarity	NPC469656
0.8421	Intermediate Similarity	NPC474846
0.8417	Intermediate Similarity	NPC105926
0.8417	Intermediate Similarity	NPC67251
0.8417	Intermediate Similarity	NPC265557
0.8417	Intermediate Similarity	NPC18945
0.8417	Intermediate Similarity	NPC91693
0.8403	Intermediate Similarity	NPC159456
0.8403	Intermediate Similarity	NPC4021
0.8374	Intermediate Similarity	NPC476854
0.8374	Intermediate Similarity	NPC476851
0.8362	Intermediate Similarity	NPC45218
0.8362	Intermediate Similarity	NPC323821
0.8362	Intermediate Similarity	NPC268238
0.8362	Intermediate Similarity	NPC143268
0.8348	Intermediate Similarity	NPC472002
0.8348	Intermediate Similarity	NPC269530
0.8347	Intermediate Similarity	NPC24651
0.8347	Intermediate Similarity	NPC469790
0.8333	Intermediate Similarity	NPC253906
0.8319	Intermediate Similarity	NPC251226
0.8306	Intermediate Similarity	NPC476863
0.8306	Intermediate Similarity	NPC476852
0.8306	Intermediate Similarity	NPC476862
0.8306	Intermediate Similarity	NPC476855
0.8291	Intermediate Similarity	NPC270478
0.8291	Intermediate Similarity	NPC179626
0.8291	Intermediate Similarity	NPC173686
0.8291	Intermediate Similarity	NPC16081
0.8288	Intermediate Similarity	NPC159533
0.8279	Intermediate Similarity	NPC477745
0.8279	Intermediate Similarity	NPC293112
0.8276	Intermediate Similarity	NPC477266
0.8264	Intermediate Similarity	NPC120724
0.8261	Intermediate Similarity	NPC317107
0.825	Intermediate Similarity	NPC477046
0.825	Intermediate Similarity	NPC470779
0.825	Intermediate Similarity	NPC102822
0.823	Intermediate Similarity	NPC180744
0.822	Intermediate Similarity	NPC470775
0.822	Intermediate Similarity	NPC474654
0.822	Intermediate Similarity	NPC477116
0.822	Intermediate Similarity	NPC176513
0.822	Intermediate Similarity	NPC122033
0.822	Intermediate Similarity	NPC27999
0.822	Intermediate Similarity	NPC287343
0.822	Intermediate Similarity	NPC53396
0.822	Intermediate Similarity	NPC470854
0.822	Intermediate Similarity	NPC97908
0.822	Intermediate Similarity	NPC98249
0.8211	Intermediate Similarity	NPC476008
0.8198	Intermediate Similarity	NPC295791
0.8197	Intermediate Similarity	NPC81736
0.8197	Intermediate Similarity	NPC470922
0.8197	Intermediate Similarity	NPC172154
0.819	Intermediate Similarity	NPC317687
0.8182	Intermediate Similarity	NPC170538
0.8167	Intermediate Similarity	NPC112038
0.8158	Intermediate Similarity	NPC322903
0.8151	Intermediate Similarity	NPC478206
0.8151	Intermediate Similarity	NPC108581
0.8151	Intermediate Similarity	NPC17772
0.8151	Intermediate Similarity	NPC284707
0.8151	Intermediate Similarity	NPC478205
0.8151	Intermediate Similarity	NPC470776
0.8142	Intermediate Similarity	NPC477090
0.8136	Intermediate Similarity	NPC207217
0.8136	Intermediate Similarity	NPC477509
0.813	Intermediate Similarity	NPC473635
0.813	Intermediate Similarity	NPC120994
0.813	Intermediate Similarity	NPC203702
0.812	Intermediate Similarity	NPC208998
0.812	Intermediate Similarity	NPC477126
0.812	Intermediate Similarity	NPC7921
0.812	Intermediate Similarity	NPC159333
0.8115	Intermediate Similarity	NPC469789
0.8115	Intermediate Similarity	NPC11895
0.8115	Intermediate Similarity	NPC472399
0.8103	Intermediate Similarity	NPC171888
0.8103	Intermediate Similarity	NPC146945
0.8095	Intermediate Similarity	NPC476193
0.8087	Intermediate Similarity	NPC469370
0.8087	Intermediate Similarity	NPC87335
0.8083	Intermediate Similarity	NPC42673
0.8083	Intermediate Similarity	NPC268958
0.8083	Intermediate Similarity	NPC230513
0.8083	Intermediate Similarity	NPC470777
0.8067	Intermediate Similarity	NPC473590
0.8067	Intermediate Similarity	NPC478204
0.8067	Intermediate Similarity	NPC296822
0.8067	Intermediate Similarity	NPC13713
0.8067	Intermediate Similarity	NPC55296
0.8053	Intermediate Similarity	NPC65523
0.8053	Intermediate Similarity	NPC283850
0.8051	Intermediate Similarity	NPC473798
0.8051	Intermediate Similarity	NPC299849
0.8051	Intermediate Similarity	NPC284915
0.8051	Intermediate Similarity	NPC117712
0.8051	Intermediate Similarity	NPC80650
0.8036	Intermediate Similarity	NPC80781
0.8017	Intermediate Similarity	NPC472004
0.8017	Intermediate Similarity	NPC17938
0.8	Intermediate Similarity	NPC289702
0.8	Intermediate Similarity	NPC188667
0.8	Intermediate Similarity	NPC472439
0.8	Intermediate Similarity	NPC204552
0.8	Intermediate Similarity	NPC477713
0.8	Intermediate Similarity	NPC477712
0.8	Intermediate Similarity	NPC469916
0.8	Intermediate Similarity	NPC208461
0.7983	Intermediate Similarity	NPC190185
0.7983	Intermediate Similarity	NPC40632
0.7983	Intermediate Similarity	NPC474333
0.7983	Intermediate Similarity	NPC251236
0.7983	Intermediate Similarity	NPC474734
0.7983	Intermediate Similarity	NPC213084
0.7983	Intermediate Similarity	NPC96312
0.7983	Intermediate Similarity	NPC328374
0.7982	Intermediate Similarity	NPC111273
0.7982	Intermediate Similarity	NPC181357
0.7982	Intermediate Similarity	NPC472645
0.7966	Intermediate Similarity	NPC94509
0.7966	Intermediate Similarity	NPC198539
0.7966	Intermediate Similarity	NPC49451
0.7965	Intermediate Similarity	NPC165608
0.7965	Intermediate Similarity	NPC474822
0.7965	Intermediate Similarity	NPC99510
0.7951	Intermediate Similarity	NPC472401
0.7951	Intermediate Similarity	NPC67569
0.7949	Intermediate Similarity	NPC194619
0.7937	Intermediate Similarity	NPC231529
0.7931	Intermediate Similarity	NPC474242
0.7931	Intermediate Similarity	NPC141350
0.792	Intermediate Similarity	NPC287423
0.7917	Intermediate Similarity	NPC146432
0.7917	Intermediate Similarity	NPC470778
0.7913	Intermediate Similarity	NPC67321
0.7913	Intermediate Similarity	NPC187435
0.7913	Intermediate Similarity	NPC474716
0.7913	Intermediate Similarity	NPC473165
0.7913	Intermediate Similarity	NPC469558
0.7913	Intermediate Similarity	NPC202524
0.7913	Intermediate Similarity	NPC112780
0.7913	Intermediate Similarity	NPC3316
0.7913	Intermediate Similarity	NPC144854
0.7903	Intermediate Similarity	NPC8374
0.7903	Intermediate Similarity	NPC8369
0.7903	Intermediate Similarity	NPC473709
0.7903	Intermediate Similarity	NPC473919
0.7895	Intermediate Similarity	NPC146731
0.7895	Intermediate Similarity	NPC477127
0.7891	Intermediate Similarity	NPC168879
0.7886	Intermediate Similarity	NPC269642
0.7886	Intermediate Similarity	NPC470265
0.7886	Intermediate Similarity	NPC19464
0.7886	Intermediate Similarity	NPC222688
0.7886	Intermediate Similarity	NPC23786
0.7881	Intermediate Similarity	NPC222834
0.7881	Intermediate Similarity	NPC474516
0.7876	Intermediate Similarity	NPC165250
0.7876	Intermediate Similarity	NPC162973
0.7869	Intermediate Similarity	NPC157252
0.7869	Intermediate Similarity	NPC471128
0.7869	Intermediate Similarity	NPC107338
0.7869	Intermediate Similarity	NPC145182
0.7869	Intermediate Similarity	NPC109607
0.7869	Intermediate Similarity	NPC471126
0.7863	Intermediate Similarity	NPC473975
0.7863	Intermediate Similarity	NPC473594
0.7863	Intermediate Similarity	NPC474586
0.7863	Intermediate Similarity	NPC5103
0.7863	Intermediate Similarity	NPC473843
0.7851	Intermediate Similarity	NPC297179
0.7846	Intermediate Similarity	NPC251998
0.7845	Intermediate Similarity	NPC154608
0.7845	Intermediate Similarity	NPC94942
0.7845	Intermediate Similarity	NPC277017
0.7845	Intermediate Similarity	NPC192813
0.7838	Intermediate Similarity	NPC199099
0.7833	Intermediate Similarity	NPC478216
0.7833	Intermediate Similarity	NPC476711
0.7833	Intermediate Similarity	NPC154363
0.7833	Intermediate Similarity	NPC234858
0.7833	Intermediate Similarity	NPC471127
0.7833	Intermediate Similarity	NPC89929
0.7833	Intermediate Similarity	NPC476710
0.7833	Intermediate Similarity	NPC471816

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 NPC240509 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	2296
0.2-0.3	3711
0.3-0.4	1826
0.4-0.5	633
0.5-0.6	227
0.6-0.7	142
0.7-0.8	13
0.8-0.85	0
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD5955	Clinical (unspecified phase)
0.8909	High Similarity	NPD4061	Clinical (unspecified phase)
0.8727	High Similarity	NPD5954	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD7115	Discovery
0.7581	Intermediate Similarity	NPD6319	Approved
0.7373	Intermediate Similarity	NPD6675	Approved
0.7373	Intermediate Similarity	NPD7128	Approved
0.7373	Intermediate Similarity	NPD5739	Approved
0.7373	Intermediate Similarity	NPD6402	Approved
0.7344	Intermediate Similarity	NPD7492	Approved
0.7333	Intermediate Similarity	NPD6373	Approved
0.7333	Intermediate Similarity	NPD6372	Approved
0.7311	Intermediate Similarity	NPD5701	Approved
0.7311	Intermediate Similarity	NPD5697	Approved
0.7302	Intermediate Similarity	NPD6059	Approved
0.7302	Intermediate Similarity	NPD6054	Approved
0.7295	Intermediate Similarity	NPD8297	Approved
0.7287	Intermediate Similarity	NPD6616	Approved
0.7266	Intermediate Similarity	NPD8328	Phase 3
0.7252	Intermediate Similarity	NPD7319	Approved
0.725	Intermediate Similarity	NPD7320	Approved
0.725	Intermediate Similarity	NPD6899	Approved
0.725	Intermediate Similarity	NPD6881	Approved
0.7244	Intermediate Similarity	NPD6921	Approved
0.7244	Intermediate Similarity	NPD6016	Approved
0.7244	Intermediate Similarity	NPD6015	Approved
0.7236	Intermediate Similarity	NPD4632	Approved
0.7231	Intermediate Similarity	NPD7078	Approved
0.7231	Intermediate Similarity	NPD8293	Discontinued
0.7227	Intermediate Similarity	NPD6008	Approved
0.7213	Intermediate Similarity	NPD6649	Approved
0.7213	Intermediate Similarity	NPD6650	Approved
0.72	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6009	Approved
0.719	Intermediate Similarity	NPD6013	Approved
0.719	Intermediate Similarity	NPD6012	Approved
0.719	Intermediate Similarity	NPD6014	Approved
0.7188	Intermediate Similarity	NPD6370	Approved
0.7188	Intermediate Similarity	NPD5988	Approved
0.7179	Intermediate Similarity	NPD5344	Discontinued
0.7176	Intermediate Similarity	NPD7736	Approved
0.7155	Intermediate Similarity	NPD4225	Approved
0.7132	Intermediate Similarity	NPD7604	Phase 2
0.7131	Intermediate Similarity	NPD6883	Approved
0.7131	Intermediate Similarity	NPD7290	Approved
0.7131	Intermediate Similarity	NPD7102	Approved
0.7109	Intermediate Similarity	NPD5983	Phase 2
0.7107	Intermediate Similarity	NPD6011	Approved
0.7094	Intermediate Similarity	NPD6648	Approved
0.7094	Intermediate Similarity	NPD7639	Approved
0.7094	Intermediate Similarity	NPD7640	Approved
0.7073	Intermediate Similarity	NPD6869	Approved
0.7073	Intermediate Similarity	NPD6847	Approved
0.7073	Intermediate Similarity	NPD8130	Phase 1
0.7073	Intermediate Similarity	NPD6617	Approved
0.7034	Intermediate Similarity	NPD1700	Approved
0.7023	Intermediate Similarity	NPD7507	Approved
0.7016	Intermediate Similarity	NPD6882	Approved
0.7009	Intermediate Similarity	NPD7638	Approved
0.6992	Remote Similarity	NPD4634	Approved
0.6975	Remote Similarity	NPD7632	Discontinued
0.6975	Remote Similarity	NPD5211	Phase 2
0.6967	Remote Similarity	NPD6686	Approved
0.6935	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4755	Approved
0.6911	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6336	Discontinued
0.6864	Remote Similarity	NPD5696	Approved
0.686	Remote Similarity	NPD5141	Approved
0.685	Remote Similarity	NPD6274	Approved
0.6822	Remote Similarity	NPD7516	Approved
0.6807	Remote Similarity	NPD4700	Approved
0.6807	Remote Similarity	NPD5285	Approved
0.6807	Remote Similarity	NPD4696	Approved
0.6807	Remote Similarity	NPD5286	Approved
0.6791	Remote Similarity	NPD6033	Approved
0.678	Remote Similarity	NPD6083	Phase 2
0.678	Remote Similarity	NPD6084	Phase 2
0.678	Remote Similarity	NPD7902	Approved
0.6752	Remote Similarity	NPD5695	Phase 3
0.6744	Remote Similarity	NPD7328	Approved
0.6744	Remote Similarity	NPD7327	Approved
0.672	Remote Similarity	NPD6371	Approved
0.6695	Remote Similarity	NPD4697	Phase 3
0.6694	Remote Similarity	NPD5225	Approved
0.6694	Remote Similarity	NPD5226	Approved
0.6694	Remote Similarity	NPD4633	Approved
0.6694	Remote Similarity	NPD5224	Approved
0.6692	Remote Similarity	NPD7100	Approved
0.6692	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD7748	Approved
0.6639	Remote Similarity	NPD5174	Approved
0.6639	Remote Similarity	NPD5175	Approved
0.6638	Remote Similarity	NPD5693	Phase 1
0.6615	Remote Similarity	NPD6314	Approved
0.6615	Remote Similarity	NPD6335	Approved
0.6615	Remote Similarity	NPD6313	Approved
0.6612	Remote Similarity	NPD5223	Approved
0.6591	Remote Similarity	NPD6908	Approved
0.6591	Remote Similarity	NPD6909	Approved
0.6591	Remote Similarity	NPD8513	Phase 3
0.6591	Remote Similarity	NPD8515	Approved
0.6591	Remote Similarity	NPD8517	Approved
0.6591	Remote Similarity	NPD8516	Approved
0.6581	Remote Similarity	NPD6399	Phase 3
0.6555	Remote Similarity	NPD5222	Approved
0.6555	Remote Similarity	NPD5221	Approved
0.6555	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD1694	Approved
0.6532	Remote Similarity	NPD4768	Approved
0.6532	Remote Similarity	NPD4767	Approved
0.6525	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD7900	Approved
0.6522	Remote Similarity	NPD6672	Approved
0.6522	Remote Similarity	NPD7260	Phase 2
0.6522	Remote Similarity	NPD5737	Approved
0.6504	Remote Similarity	NPD4754	Approved
0.65	Remote Similarity	NPD5173	Approved
0.6496	Remote Similarity	NPD7515	Phase 2
0.6491	Remote Similarity	NPD3618	Phase 1
0.6491	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6053	Discontinued
0.648	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6412	Phase 2
0.6475	Remote Similarity	NPD6845	Suspended
0.6466	Remote Similarity	NPD8380	Approved
0.6466	Remote Similarity	NPD8379	Approved
0.6466	Remote Similarity	NPD8335	Approved
0.6466	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD8296	Approved
0.6466	Remote Similarity	NPD5328	Approved
0.6466	Remote Similarity	NPD8378	Approved
0.6462	Remote Similarity	NPD6868	Approved
0.6441	Remote Similarity	NPD5778	Approved
0.6441	Remote Similarity	NPD5779	Approved
0.6435	Remote Similarity	NPD3573	Approved
0.6429	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4729	Approved
0.6429	Remote Similarity	NPD5128	Approved
0.6429	Remote Similarity	NPD4730	Approved
0.641	Remote Similarity	NPD6698	Approved
0.641	Remote Similarity	NPD46	Approved
0.6391	Remote Similarity	NPD8294	Approved
0.6391	Remote Similarity	NPD8377	Approved
0.6387	Remote Similarity	NPD5282	Discontinued
0.6364	Remote Similarity	NPD6334	Approved
0.6364	Remote Similarity	NPD6333	Approved
0.6356	Remote Similarity	NPD6079	Approved
0.635	Remote Similarity	NPD8074	Phase 3
0.6343	Remote Similarity	NPD8033	Approved
0.6333	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5250	Approved
0.6328	Remote Similarity	NPD5251	Approved
0.6328	Remote Similarity	NPD5248	Approved
0.6328	Remote Similarity	NPD5249	Phase 3
0.6328	Remote Similarity	NPD5247	Approved
0.6325	Remote Similarity	NPD6673	Approved
0.6325	Remote Similarity	NPD6904	Approved
0.6325	Remote Similarity	NPD6080	Approved
0.6325	Remote Similarity	NPD4753	Phase 2
0.6308	Remote Similarity	NPD8133	Approved
0.6303	Remote Similarity	NPD4202	Approved
0.6279	Remote Similarity	NPD5217	Approved
0.6279	Remote Similarity	NPD5215	Approved
0.6279	Remote Similarity	NPD5216	Approved
0.625	Remote Similarity	NPD6001	Approved
0.6222	Remote Similarity	NPD7503	Approved
0.6218	Remote Similarity	NPD6411	Approved
0.6218	Remote Similarity	NPD8035	Phase 2
0.6218	Remote Similarity	NPD8034	Phase 2
0.6216	Remote Similarity	NPD3617	Approved
0.6214	Remote Similarity	NPD5956	Approved
0.621	Remote Similarity	NPD4159	Approved
0.6207	Remote Similarity	NPD5330	Approved
0.6207	Remote Similarity	NPD6409	Approved
0.6207	Remote Similarity	NPD6684	Approved
0.6207	Remote Similarity	NPD7146	Approved
0.6207	Remote Similarity	NPD7521	Approved
0.6207	Remote Similarity	NPD7334	Approved
0.6202	Remote Similarity	NPD5135	Approved
0.6202	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD5169	Approved
0.6198	Remote Similarity	NPD5210	Approved
0.6198	Remote Similarity	NPD4629	Approved
0.6154	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5127	Approved
0.6134	Remote Similarity	NPD5692	Phase 3
0.6121	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6903	Approved
0.6102	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7983	Approved
0.6083	Remote Similarity	NPD5284	Approved
0.6083	Remote Similarity	NPD7637	Suspended
0.6083	Remote Similarity	NPD5281	Approved
0.6083	Remote Similarity	NPD5694	Approved
0.6083	Remote Similarity	NPD6050	Approved
0.6068	Remote Similarity	NPD6098	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