NPASS Compound

Structure

NPC472250 OpenBabel07101719142D 46 48 0 0 1 0 0 0 0 0999 V2000 -2.2879 -0.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3504 3.0883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1324 -1.2742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5031 4.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1952 2.6083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6531 -1.6041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8239 1.7677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6212 2.3471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1854 3.2025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6763 1.7630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8449 2.2430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6763 0.8030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0135 1.7630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8449 0.3230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5655 0.5453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8621 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1681 3.2078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4800 -0.8314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8520 -0.0971 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5453 2.5655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4190 -0.6318 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3523 4.8890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2365 2.5580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 -2.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3912 0.9107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0135 0.8030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1071 3.4074 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6424 0.7134 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8420 1.6524 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5194 0.3230 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0202 3.1108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9130 -0.2967 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1821 0.3230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6625 2.3973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4025 5.8476 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1908 4.1683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8982 -3.0857 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9170 0.1075 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5430 3.9159 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1821 -0.6370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1574 4.3661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8006 1.7027 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8628 -1.2553 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3508 0.8030 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4327 0.8570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 2 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 7 25 1 0 0 0 0 8 34 1 0 0 0 0 9 34 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 2 0 0 0 0 13 26 2 0 0 0 0 14 26 1 0 0 0 0 15 16 2 0 0 0 0 15 19 1 0 0 0 0 16 34 1 0 0 0 0 17 20 1 0 0 0 0 17 27 1 0 0 0 0 18 21 1 0 0 0 0 18 35 1 0 0 0 0 19 1 1 1 0 0 0 19 32 1 0 0 0 0 20 29 1 0 0 0 0 21 3 1 6 0 0 0 21 30 1 0 0 0 0 22 36 2 0 0 0 0 22 42 1 0 0 0 0 23 37 2 0 0 0 0 23 43 1 0 0 0 0 24 38 2 0 0 0 0 24 44 1 0 0 0 0 25 39 2 0 0 0 0 25 46 1 0 0 0 0 26 33 1 0 0 0 0 27 31 1 0 0 0 0 27 42 1 0 0 0 0 28 29 1 0 0 0 0 28 30 1 0 0 0 0 28 35 1 1 0 0 0 29 43 1 6 0 0 0 30 45 1 1 0 0 0 31 34 1 0 0 0 0 31 40 2 0 0 0 0 32 35 1 6 0 0 0 32 44 1 0 0 0 0 33 41 2 0 0 0 0 33 45 1 0 0 0 0 35 46 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	640.29
Volume:	655.938
LogP:	3.76
LogD:	2.162
LogS:	-4.445
# Rotatable Bonds:	11
TPSA:	148.57
# H-Bond Aceptor:	11
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.242
Synthetic Accessibility Score:	5.549
Fsp3:	0.543
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:	-5.128
MDCK Permeability:	0.00010590510646579787
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.96
20% Bioavailability (F20%):	0.644
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	81.42635345458984%
Volume Distribution (VD):	1.903
Pgp-substrate:	9.151482582092285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.027
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.7
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.18
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.879
CYP3A4-substrate:	0.557

ADMET: Excretion

Clearance (CL):	3.095
Half-life (T1/2):	0.816

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.998
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.733
Maximum Recommended Daily Dose:	0.493
Skin Sensitization:	0.051
Carcinogencity:	0.057
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.82

Download Data

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

Natural Product: NPC472250

Natural Product ID:	NPC472250
*Common Name:**	IFUGWILNBFHLFO-IMYARSFSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IFUGWILNBFHLFO-IMYARSFSSA-N
Standard InCHI:	InChI=1S/C35H44O11/c1-19-15-16-34(8,9)31(40)27(42-22(4)36)17-20(2)29(43-23(5)37)28-30(45-33(41)26-13-11-10-12-14-26)21(3)18-35(28,46-25(7)39)32(19)44-24(6)38/h10-16,19,21,27-30,32H,2,17-18H2,1,3-9H3/b16-15+/t19-,21+,27?,28-,29-,30-,32+,35+/m0/s1
SMILES:	CC(=O)O[C@H]1C(=C)CC(OC(=O)C)C(=O)C(C)(C)/C=C/[C@@H]([C@H]([C@@]2([C@@H]1[C@@H](OC(=O)c1ccccc1)[C@@H](C2)C)OC(=O)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3354234
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002877] Jatrophane and cyclojatrophane diterpenoids

*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
NPO33056	euphorbia squamosa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25437914]

☑ 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	3
Others	11

Activity Type	# Activity
Organism	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC50	=	2300.0	nM	PMID[478670]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC50	=	31700.0	nM	PMID[478670]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC50	=	25000.0	nM	PMID[478670]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Ratio IC50	=	13.8	n.a.	PMID[478670]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Ratio IC50	=	10.9	n.a.	PMID[478670]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	FIC50	=	1.2	n.a.	PMID[478670]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	FIC50	=	0.04	n.a.	PMID[478670]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	FIC50	=	1.0	n.a.	PMID[478670]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	FIC50	=	0.07	n.a.	PMID[478670]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	FIC50	=	0.02	n.a.	PMID[478670]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	FICI	=	1.27	n.a.	PMID[478670]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	FICI	=	0.06	n.a.	PMID[478670]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	FICI	=	1.02	n.a.	PMID[478670]

☑ 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 NPC472250 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	321
0.1-0.2	1126
0.2-0.3	2389
0.3-0.4	6082
0.4-0.5	11290
0.5-0.6	13754
0.6-0.7	6721
0.7-0.8	805
0.8-0.85	58
0.85-0.9	62
0.9-0.95	59
0.95-1	30

Similarity Score	Similarity Level	Natural Product ID
0.9921	High Similarity	NPC475262
0.9921	High Similarity	NPC265459
0.9921	High Similarity	NPC290833
0.9844	High Similarity	NPC285221
0.9844	High Similarity	NPC194769
0.9767	High Similarity	NPC86772
0.9692	High Similarity	NPC272523
0.9692	High Similarity	NPC325805
0.9618	High Similarity	NPC475660
0.9612	High Similarity	NPC79699
0.9612	High Similarity	NPC270364
0.9545	High Similarity	NPC474303
0.9545	High Similarity	NPC473497
0.9545	High Similarity	NPC475413
0.9403	High Similarity	NPC45307
0.9403	High Similarity	NPC82467
0.9403	High Similarity	NPC477094
0.9403	High Similarity	NPC477096
0.9394	High Similarity	NPC276652
0.9375	High Similarity	NPC475508
0.9323	High Similarity	NPC251294
0.9254	High Similarity	NPC473654
0.9237	High Similarity	NPC153617
0.9231	High Similarity	NPC233860
0.9225	High Similarity	NPC42234
0.9197	High Similarity	NPC477095
0.9197	High Similarity	NPC170668
0.9167	High Similarity	NPC472247
0.916	High Similarity	NPC472248
0.913	High Similarity	NPC205389
0.9118	High Similarity	NPC153214
0.9111	High Similarity	NPC187566
0.9091	High Similarity	NPC324898
0.9091	High Similarity	NPC28836
0.9091	High Similarity	NPC298547
0.9091	High Similarity	NPC134937
0.9084	High Similarity	NPC239358
0.9084	High Similarity	NPC477360
0.9077	High Similarity	NPC272946
0.9023	High Similarity	NPC200154
0.9023	High Similarity	NPC149401
0.9023	High Similarity	NPC279637
0.9	High Similarity	NPC477099
0.9	High Similarity	NPC232583
0.9	High Similarity	NPC25484
0.9	High Similarity	NPC477101
0.9	High Similarity	NPC477097
0.8971	High Similarity	NPC242355
0.8955	High Similarity	NPC202729
0.8955	High Similarity	NPC477358
0.8947	High Similarity	NPC311492
0.8947	High Similarity	NPC477368
0.8939	High Similarity	NPC233692
0.8931	High Similarity	NPC122504
0.8931	High Similarity	NPC3450
0.8931	High Similarity	NPC475671
0.8931	High Similarity	NPC475452
0.8889	High Similarity	NPC27721
0.8889	High Similarity	NPC205305
0.8889	High Similarity	NPC327511
0.8881	High Similarity	NPC477367
0.8881	High Similarity	NPC232888
0.8872	High Similarity	NPC477364
0.8824	High Similarity	NPC53361
0.8824	High Similarity	NPC473301
0.8824	High Similarity	NPC121268
0.8811	High Similarity	NPC477098
0.8811	High Similarity	NPC477100
0.8806	High Similarity	NPC477359
0.876	High Similarity	NPC8990
0.8732	High Similarity	NPC125033
0.8692	High Similarity	NPC477369
0.869	High Similarity	NPC70344
0.8633	High Similarity	NPC475135
0.8571	High Similarity	NPC191387
0.8571	High Similarity	NPC131966
0.84	Intermediate Similarity	NPC55744
0.8358	Intermediate Similarity	NPC477370
0.8346	Intermediate Similarity	NPC477363
0.8346	Intermediate Similarity	NPC477366
0.8333	Intermediate Similarity	NPC477362
0.8322	Intermediate Similarity	NPC471100
0.8322	Intermediate Similarity	NPC471107
0.831	Intermediate Similarity	NPC95449
0.8296	Intermediate Similarity	NPC37968
0.8284	Intermediate Similarity	NPC477357
0.8284	Intermediate Similarity	NPC472706
0.8284	Intermediate Similarity	NPC477365
0.8252	Intermediate Similarity	NPC470231
0.8243	Intermediate Similarity	NPC469456
0.8227	Intermediate Similarity	NPC162613
0.8227	Intermediate Similarity	NPC87934
0.8222	Intermediate Similarity	NPC472707
0.8219	Intermediate Similarity	NPC254558
0.8195	Intermediate Similarity	NPC472704
0.8169	Intermediate Similarity	NPC266374
0.8168	Intermediate Similarity	NPC473243
0.8163	Intermediate Similarity	NPC51602
0.8156	Intermediate Similarity	NPC9905
0.8138	Intermediate Similarity	NPC475552
0.8129	Intermediate Similarity	NPC4242
0.8129	Intermediate Similarity	NPC471911
0.812	Intermediate Similarity	NPC472703
0.8116	Intermediate Similarity	NPC475569
0.8116	Intermediate Similarity	NPC472394
0.8112	Intermediate Similarity	NPC182869
0.8112	Intermediate Similarity	NPC472546
0.8112	Intermediate Similarity	NPC192658
0.8108	Intermediate Similarity	NPC283875
0.8108	Intermediate Similarity	NPC469647
0.8108	Intermediate Similarity	NPC138641
0.8108	Intermediate Similarity	NPC469648
0.8108	Intermediate Similarity	NPC22571
0.8074	Intermediate Similarity	NPC476599
0.8071	Intermediate Similarity	NPC66761
0.8071	Intermediate Similarity	NPC17877
0.8071	Intermediate Similarity	NPC472577
0.8071	Intermediate Similarity	NPC291638
0.8071	Intermediate Similarity	NPC195647
0.8069	Intermediate Similarity	NPC134131
0.8069	Intermediate Similarity	NPC25043
0.8069	Intermediate Similarity	NPC127857
0.8041	Intermediate Similarity	NPC471103
0.8041	Intermediate Similarity	NPC161955
0.8041	Intermediate Similarity	NPC472398
0.8028	Intermediate Similarity	NPC170718
0.8027	Intermediate Similarity	NPC473403
0.8014	Intermediate Similarity	NPC478263
0.8014	Intermediate Similarity	NPC312393
0.8	Intermediate Similarity	NPC474608
0.8	Intermediate Similarity	NPC473670
0.8	Intermediate Similarity	NPC282239
0.8	Intermediate Similarity	NPC34943
0.8	Intermediate Similarity	NPC473611
0.8	Intermediate Similarity	NPC21410
0.7987	Intermediate Similarity	NPC233581
0.7987	Intermediate Similarity	NPC145649
0.7986	Intermediate Similarity	NPC51181
0.7986	Intermediate Similarity	NPC183540
0.7973	Intermediate Similarity	NPC470245
0.7973	Intermediate Similarity	NPC473214
0.7973	Intermediate Similarity	NPC7095
0.7973	Intermediate Similarity	NPC112216
0.7972	Intermediate Similarity	NPC184747
0.7972	Intermediate Similarity	NPC48017
0.7972	Intermediate Similarity	NPC473758
0.7972	Intermediate Similarity	NPC211137
0.7972	Intermediate Similarity	NPC147880
0.7972	Intermediate Similarity	NPC4341
0.7972	Intermediate Similarity	NPC476094
0.7972	Intermediate Similarity	NPC473112
0.7972	Intermediate Similarity	NPC473613
0.7972	Intermediate Similarity	NPC473109
0.7972	Intermediate Similarity	NPC473081
0.7972	Intermediate Similarity	NPC200592
0.7972	Intermediate Similarity	NPC43241
0.7972	Intermediate Similarity	NPC473060
0.7972	Intermediate Similarity	NPC473085
0.7971	Intermediate Similarity	NPC147561
0.7971	Intermediate Similarity	NPC82712
0.7959	Intermediate Similarity	NPC327031
0.7947	Intermediate Similarity	NPC106895
0.7947	Intermediate Similarity	NPC11410
0.7947	Intermediate Similarity	NPC217091
0.7945	Intermediate Similarity	NPC125882
0.7945	Intermediate Similarity	NPC478264
0.7937	Intermediate Similarity	NPC469636
0.7919	Intermediate Similarity	NPC306799
0.7919	Intermediate Similarity	NPC101043
0.7919	Intermediate Similarity	NPC96308
0.7917	Intermediate Similarity	NPC16912
0.7914	Intermediate Similarity	NPC72915
0.7905	Intermediate Similarity	NPC60509
0.7905	Intermediate Similarity	NPC81698
0.7905	Intermediate Similarity	NPC476975
0.7905	Intermediate Similarity	NPC250046
0.7905	Intermediate Similarity	NPC473215
0.7905	Intermediate Similarity	NPC76103
0.7902	Intermediate Similarity	NPC214550
0.7902	Intermediate Similarity	NPC210591
0.7902	Intermediate Similarity	NPC475652
0.7895	Intermediate Similarity	NPC472393
0.7891	Intermediate Similarity	NPC240115
0.7891	Intermediate Similarity	NPC20255
0.7891	Intermediate Similarity	NPC473602
0.7891	Intermediate Similarity	NPC209592
0.7891	Intermediate Similarity	NPC48599
0.7887	Intermediate Similarity	NPC217673
0.7887	Intermediate Similarity	NPC52523
0.7881	Intermediate Similarity	NPC473632
0.7881	Intermediate Similarity	NPC251139
0.7881	Intermediate Similarity	NPC132599
0.7881	Intermediate Similarity	NPC469730
0.7868	Intermediate Similarity	NPC246166
0.7857	Intermediate Similarity	NPC238370
0.7857	Intermediate Similarity	NPC329997
0.7857	Intermediate Similarity	NPC469499
0.7852	Intermediate Similarity	NPC165260
0.7852	Intermediate Similarity	NPC161239
0.7852	Intermediate Similarity	NPC476173

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 NPC472250 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	774
0.2-0.3	1668
0.3-0.4	2947
0.4-0.5	2167
0.5-0.6	1067
0.6-0.7	237
0.7-0.8	16
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8194	Intermediate Similarity	NPD7236	Approved
0.8041	Intermediate Similarity	NPD7239	Suspended
0.7911	Intermediate Similarity	NPD7799	Discontinued
0.7676	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD7057	Phase 3
0.7564	Intermediate Similarity	NPD7058	Phase 2
0.7538	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD2067	Discontinued
0.7444	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD2182	Approved
0.7319	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD6685	Approved
0.7123	Intermediate Similarity	NPD7961	Discontinued
0.7105	Intermediate Similarity	NPD4628	Phase 3
0.7103	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8368	Discontinued
0.7077	Intermediate Similarity	NPD164	Approved
0.7059	Intermediate Similarity	NPD2629	Approved
0.7059	Intermediate Similarity	NPD8407	Phase 2
0.7037	Intermediate Similarity	NPD7094	Approved
0.7037	Intermediate Similarity	NPD6858	Approved
0.7025	Intermediate Similarity	NPD6599	Discontinued
0.7021	Intermediate Similarity	NPD6287	Discontinued
0.7007	Intermediate Similarity	NPD4198	Discontinued
0.7	Intermediate Similarity	NPD5765	Approved
0.7	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6765	Approved
0.6982	Remote Similarity	NPD6764	Approved
0.6982	Remote Similarity	NPD7685	Pre-registration
0.6978	Remote Similarity	NPD7741	Discontinued
0.6963	Remote Similarity	NPD6912	Phase 3
0.6933	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6004	Phase 3
0.6908	Remote Similarity	NPD6005	Phase 3
0.6908	Remote Similarity	NPD6002	Phase 3
0.6899	Remote Similarity	NPD1238	Approved
0.6897	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6085	Phase 2
0.6894	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD8434	Phase 2
0.6871	Remote Similarity	NPD7075	Discontinued
0.687	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6799	Approved
0.6857	Remote Similarity	NPD9545	Approved
0.6839	Remote Similarity	NPD3887	Approved
0.6838	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6784	Approved
0.6821	Remote Similarity	NPD6785	Approved
0.6805	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.68	Remote Similarity	NPD8435	Approved
0.68	Remote Similarity	NPD6355	Discontinued
0.6759	Remote Similarity	NPD5667	Approved
0.6755	Remote Similarity	NPD6653	Approved
0.6742	Remote Similarity	NPD6647	Phase 2
0.6741	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7137	Phase 2
0.6731	Remote Similarity	NPD6190	Approved
0.6728	Remote Similarity	NPD6801	Discontinued
0.6724	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD8361	Approved
0.6705	Remote Similarity	NPD8360	Approved
0.6688	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD5763	Approved
0.6688	Remote Similarity	NPD5762	Approved
0.6687	Remote Similarity	NPD5761	Phase 2
0.6687	Remote Similarity	NPD5760	Phase 2
0.6667	Remote Similarity	NPD6273	Approved
0.6647	Remote Similarity	NPD8127	Discontinued
0.6646	Remote Similarity	NPD3817	Phase 2
0.6644	Remote Similarity	NPD1876	Approved
0.6644	Remote Similarity	NPD7008	Discontinued
0.6625	Remote Similarity	NPD5403	Approved
0.6625	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD3972	Approved
0.6621	Remote Similarity	NPD6637	Approved
0.6604	Remote Similarity	NPD5401	Approved
0.66	Remote Similarity	NPD3764	Approved
0.6599	Remote Similarity	NPD6362	Approved
0.6591	Remote Similarity	NPD8150	Discontinued
0.6585	Remote Similarity	NPD7819	Suspended
0.6581	Remote Similarity	NPD2353	Approved
0.6581	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD230	Phase 1
0.6577	Remote Similarity	NPD6832	Phase 2
0.6575	Remote Similarity	NPD8485	Approved
0.6567	Remote Similarity	NPD1237	Approved
0.6558	Remote Similarity	NPD7305	Phase 1
0.6556	Remote Similarity	NPD7713	Phase 3
0.6554	Remote Similarity	NPD5647	Approved
0.6552	Remote Similarity	NPD4807	Approved
0.6552	Remote Similarity	NPD4806	Approved
0.6545	Remote Similarity	NPD5402	Approved
0.6543	Remote Similarity	NPD7458	Discontinued
0.6528	Remote Similarity	NPD5305	Approved
0.6528	Remote Similarity	NPD17	Approved
0.6528	Remote Similarity	NPD5306	Approved
0.6516	Remote Similarity	NPD2796	Approved
0.6515	Remote Similarity	NPD7798	Approved
0.651	Remote Similarity	NPD3664	Approved
0.651	Remote Similarity	NPD3662	Phase 3
0.651	Remote Similarity	NPD3663	Approved
0.651	Remote Similarity	NPD3661	Approved
0.65	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD2569	Approved
0.6494	Remote Similarity	NPD2567	Approved
0.6493	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD1929	Approved
0.6493	Remote Similarity	NPD1930	Approved
0.6475	Remote Similarity	NPD969	Suspended
0.6467	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7055	Discontinued
0.6454	Remote Similarity	NPD4766	Approved
0.6454	Remote Similarity	NPD5951	Approved
0.6449	Remote Similarity	NPD4233	Approved
0.6449	Remote Similarity	NPD4234	Approved
0.6447	Remote Similarity	NPD8032	Phase 2
0.6447	Remote Similarity	NPD6663	Approved
0.6444	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD9495	Approved
0.6429	Remote Similarity	NPD919	Approved
0.6416	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD2354	Approved
0.6403	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD4380	Phase 2
0.64	Remote Similarity	NPD5736	Approved
0.6397	Remote Similarity	NPD5048	Discontinued
0.6395	Remote Similarity	NPD1608	Approved
0.6391	Remote Similarity	NPD5494	Approved
0.6391	Remote Similarity	NPD2066	Phase 3
0.6389	Remote Similarity	NPD7009	Phase 2
0.6385	Remote Similarity	NPD1202	Approved
0.6375	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.637	Remote Similarity	NPD4106	Approved
0.637	Remote Similarity	NPD4135	Approved
0.637	Remote Similarity	NPD4136	Approved
0.6369	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6385	Approved
0.6364	Remote Similarity	NPD7497	Discontinued
0.6364	Remote Similarity	NPD6386	Approved
0.6357	Remote Similarity	NPD8297	Approved
0.6352	Remote Similarity	NPD2575	Approved
0.6352	Remote Similarity	NPD8166	Discontinued
0.6352	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD9259	Approved
0.6349	Remote Similarity	NPD9257	Approved
0.6347	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD5353	Approved
0.6346	Remote Similarity	NPD7033	Discontinued
0.6346	Remote Similarity	NPD3748	Approved
0.634	Remote Similarity	NPD6233	Phase 2
0.6337	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD1693	Approved
0.6324	Remote Similarity	NPD5909	Discontinued
0.6319	Remote Similarity	NPD7610	Discontinued
0.6319	Remote Similarity	NPD920	Approved
0.6316	Remote Similarity	NPD7095	Approved
0.6316	Remote Similarity	NPD6039	Approved
0.631	Remote Similarity	NPD3882	Suspended
0.631	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD2199	Approved
0.6309	Remote Similarity	NPD2198	Approved
0.6306	Remote Similarity	NPD2438	Suspended
0.6301	Remote Similarity	NPD5126	Approved
0.6301	Remote Similarity	NPD5125	Phase 3
0.6296	Remote Similarity	NPD2534	Approved
0.6296	Remote Similarity	NPD2532	Approved
0.6296	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2533	Approved
0.6291	Remote Similarity	NPD5204	Approved
0.6291	Remote Similarity	NPD7084	Phase 3
0.6288	Remote Similarity	NPD1989	Approved
0.6279	Remote Similarity	NPD3673	Approved
0.6279	Remote Similarity	NPD3672	Approved
0.6275	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6798	Discontinued
0.6272	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD8462	Phase 1
0.6268	Remote Similarity	NPD2652	Approved
0.6268	Remote Similarity	NPD2650	Approved
0.6267	Remote Similarity	NPD3267	Approved
0.6267	Remote Similarity	NPD3266	Approved
0.6265	Remote Similarity	NPD7411	Suspended
0.626	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.625	Remote Similarity	NPD9493	Approved
0.625	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4110	Phase 3
0.625	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD2799	Discontinued
0.6242	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD4105	Approved
0.6233	Remote Similarity	NPD4102	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