NPASS Compound

Structure

NPC471940 OpenBabel07101719512D 46 49 0 0 1 0 0 0 0 0999 V2000 -11.6934 0.7696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4996 5.1696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9865 4.2812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7784 2.4214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1166 3.9765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1016 4.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8200 0.2826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9615 0.7955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0881 0.3085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2297 0.8214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3563 0.3344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4978 0.8473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6244 0.3603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7660 0.8732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8925 0.3862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0341 0.8991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1607 0.4121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0184 2.7001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7285 -0.4163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9866 4.2962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8274 2.1123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2582 3.4636 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2282 5.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2093 2.1123 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3022 0.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4147 1.9508 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5184 1.1613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3847 3.9506 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2804 0.9599 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4587 2.4378 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9675 0.3267 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9715 0.2371 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4737 3.4377 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2731 2.4637 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5184 1.1613 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5411 -1.3986 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2133 6.4633 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4288 0.4380 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1061 0.3523 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4804 -0.5317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4736 3.4227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8528 1.5564 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7495 0.5219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3698 4.9505 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3172 1.9249 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 7 1 0 0 0 0 2 20 2 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 23 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 17 25 1 0 0 0 0 18 21 2 0 0 0 0 18 24 1 0 0 0 0 19 36 1 0 0 0 0 20 33 1 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 22 34 1 1 0 0 0 23 37 2 0 0 0 0 23 44 1 0 0 0 0 24 34 1 6 0 0 0 24 35 1 0 0 0 0 25 38 2 0 0 0 0 25 45 1 0 0 0 0 26 29 1 0 0 0 0 26 30 1 0 0 0 0 26 34 1 1 0 0 0 27 35 1 0 0 0 0 27 39 2 0 0 0 0 28 33 1 6 0 0 0 28 44 1 0 0 0 0 29 32 1 1 0 0 0 29 46 1 0 0 0 0 30 33 1 1 0 0 0 30 45 1 0 0 0 0 31 32 1 6 0 0 0 31 35 1 0 0 0 0 31 40 1 0 0 0 0 32 19 1 6 0 0 0 32 46 1 0 0 0 0 33 41 1 1 0 0 0 34 42 1 1 0 0 0 35 43 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	646.34
Volume:	657.927
LogP:	4.351
LogD:	2.183
LogS:	-3.984
# Rotatable Bonds:	15
TPSA:	183.35
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.049
Synthetic Accessibility Score:	5.687
Fsp3:	0.686
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:	-5.002
MDCK Permeability:	3.6477300454862416e-05
Pgp-inhibitor:	0.979
Pgp-substrate:	0.371
Human Intestinal Absorption (HIA):	0.916
20% Bioavailability (F20%):	0.561
30% Bioavailability (F30%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122
Plasma Protein Binding (PPB):	89.26116943359375%
Volume Distribution (VD):	1.275
Pgp-substrate:	6.564733505249023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.232
CYP2C9-inhibitor:	0.314
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.571
CYP3A4-substrate:	0.123

ADMET: Excretion

Clearance (CL):	1.626
Half-life (T1/2):	0.175

ADMET: Toxicity

hERG Blockers:	0.75
Human Hepatotoxicity (H-HT):	0.96
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.092
Rat Oral Acute Toxicity:	0.939
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.899
Carcinogencity:	0.087
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC471940

Natural Product ID:	NPC471940
*Common Name:**	CEEFNBYRKPOUJV-GBSKIJSSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CEEFNBYRKPOUJV-GBSKIJSSSA-N
Standard InCHI:	InChI=1S/C35H50O11/c1-7-8-9-10-11-12-13-14-15-16-17-25(38)45-30-26-29-32(19-36,46-29)31(40)35(43)24(18-21(4)27(35)39)34(26,42)22(5)28(44-23(6)37)33(30,41)20(2)3/h14-18,22,24,26,28-31,36,40-43H,2,7-13,19H2,1,3-6H3/b15-14+,17-16+/t22-,24+,26+,28-,29+,30-,31-,32+,33+,34+,35-/m1/s1
SMILES:	CCCCCCCC/C=C/C=C/C(=O)O[C@@H]1[C@@H]2[C@@H]3O[C@]3(CO)[C@H]([C@]3([C@H]([C@@]2(O)[C@@H]([C@H]([C@@]1(O)C(=C)C)OC(=O)C)C)C=C(C3=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3309439
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:0003494] Rhamnofolane and daphnane 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
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[15997133]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[16141313]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	callus	n.a.	PMID[22368856]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23611151]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[24931277]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562066]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	24.0	nM	PMID[495386]

☑ 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 NPC471940 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	260
0.1-0.2	1450
0.2-0.3	4122
0.3-0.4	6831
0.4-0.5	12316
0.5-0.6	11909
0.6-0.7	4656
0.7-0.8	970
0.8-0.85	75
0.85-0.9	68
0.9-0.95	28
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9914	High Similarity	NPC471939
0.9828	High Similarity	NPC473709
0.9828	High Similarity	NPC473919
0.9741	High Similarity	NPC473802
0.9417	High Similarity	NPC236999
0.935	High Similarity	NPC475154
0.935	High Similarity	NPC475500
0.935	High Similarity	NPC182266
0.935	High Similarity	NPC471136
0.935	High Similarity	NPC223356
0.935	High Similarity	NPC100017
0.935	High Similarity	NPC471137
0.935	High Similarity	NPC473548
0.92	High Similarity	NPC68282
0.9187	High Similarity	NPC473485
0.9187	High Similarity	NPC475139
0.9187	High Similarity	NPC180902
0.9187	High Similarity	NPC474508
0.9167	High Similarity	NPC145238
0.9106	High Similarity	NPC475606
0.9106	High Similarity	NPC477189
0.9106	High Similarity	NPC251564
0.9106	High Similarity	NPC475314
0.9083	High Similarity	NPC472399
0.9024	High Similarity	NPC162495
0.9	High Similarity	NPC162009
0.9	High Similarity	NPC19464
0.9	High Similarity	NPC257017
0.8917	High Similarity	NPC52839
0.8917	High Similarity	NPC472401
0.8862	High Similarity	NPC475273
0.8862	High Similarity	NPC168849
0.8833	High Similarity	NPC329080
0.8833	High Similarity	NPC472759
0.8833	High Similarity	NPC185876
0.8833	High Similarity	NPC145182
0.8833	High Similarity	NPC157252
0.8833	High Similarity	NPC475885
0.8833	High Similarity	NPC471128
0.8833	High Similarity	NPC471126
0.8833	High Similarity	NPC19336
0.878	High Similarity	NPC217901
0.875	High Similarity	NPC471108
0.875	High Similarity	NPC22628
0.875	High Similarity	NPC236918
0.875	High Similarity	NPC156745
0.875	High Similarity	NPC5989
0.875	High Similarity	NPC255081
0.875	High Similarity	NPC275696
0.875	High Similarity	NPC5991
0.875	High Similarity	NPC180640
0.8667	High Similarity	NPC472397
0.8667	High Similarity	NPC146280
0.8667	High Similarity	NPC124676
0.8667	High Similarity	NPC171905
0.8667	High Similarity	NPC472758
0.8667	High Similarity	NPC471125
0.8667	High Similarity	NPC472760
0.8651	High Similarity	NPC473838
0.8651	High Similarity	NPC475389
0.8595	High Similarity	NPC470186
0.8583	High Similarity	NPC10721
0.8583	High Similarity	NPC153651
0.8583	High Similarity	NPC156252
0.85	High Similarity	NPC471127
0.85	High Similarity	NPC234858
0.85	High Similarity	NPC154363
0.8492	Intermediate Similarity	NPC476078
0.8492	Intermediate Similarity	NPC476091
0.8443	Intermediate Similarity	NPC472667
0.8417	Intermediate Similarity	NPC474872
0.8417	Intermediate Similarity	NPC472400
0.8374	Intermediate Similarity	NPC475003
0.8346	Intermediate Similarity	NPC270109
0.8333	Intermediate Similarity	NPC474937
0.8333	Intermediate Similarity	NPC473635
0.8333	Intermediate Similarity	NPC293112
0.8333	Intermediate Similarity	NPC472757
0.8333	Intermediate Similarity	NPC71889
0.8295	Intermediate Similarity	NPC470185
0.8291	Intermediate Similarity	NPC474716
0.8264	Intermediate Similarity	NPC73314
0.8254	Intermediate Similarity	NPC172154
0.8254	Intermediate Similarity	NPC81736
0.825	Intermediate Similarity	NPC265499
0.825	Intermediate Similarity	NPC89227
0.825	Intermediate Similarity	NPC170212
0.825	Intermediate Similarity	NPC151216
0.825	Intermediate Similarity	NPC471933
0.825	Intermediate Similarity	NPC101825
0.825	Intermediate Similarity	NPC215643
0.825	Intermediate Similarity	NPC17138
0.825	Intermediate Similarity	NPC475391
0.825	Intermediate Similarity	NPC221511
0.8226	Intermediate Similarity	NPC143755
0.8211	Intermediate Similarity	NPC284707
0.8197	Intermediate Similarity	NPC477509
0.8189	Intermediate Similarity	NPC222307
0.8182	Intermediate Similarity	NPC469463
0.8182	Intermediate Similarity	NPC477126
0.8182	Intermediate Similarity	NPC469496
0.8182	Intermediate Similarity	NPC469454
0.8175	Intermediate Similarity	NPC469352
0.8175	Intermediate Similarity	NPC469789
0.8175	Intermediate Similarity	NPC11895
0.8167	Intermediate Similarity	NPC174471
0.8167	Intermediate Similarity	NPC474871
0.8167	Intermediate Similarity	NPC158523
0.8167	Intermediate Similarity	NPC260786
0.8167	Intermediate Similarity	NPC475937
0.8167	Intermediate Similarity	NPC96739
0.816	Intermediate Similarity	NPC310511
0.8151	Intermediate Similarity	NPC273433
0.814	Intermediate Similarity	NPC475371
0.814	Intermediate Similarity	NPC231529
0.8136	Intermediate Similarity	NPC266514
0.813	Intermediate Similarity	NPC53396
0.813	Intermediate Similarity	NPC98249
0.813	Intermediate Similarity	NPC469684
0.812	Intermediate Similarity	NPC474741
0.8115	Intermediate Similarity	NPC133677
0.8115	Intermediate Similarity	NPC138303
0.8115	Intermediate Similarity	NPC67290
0.8099	Intermediate Similarity	NPC317687
0.8095	Intermediate Similarity	NPC170538
0.8095	Intermediate Similarity	NPC23786
0.8095	Intermediate Similarity	NPC470265
0.8083	Intermediate Similarity	NPC153036
0.808	Intermediate Similarity	NPC472004
0.8067	Intermediate Similarity	NPC29827
0.8065	Intermediate Similarity	NPC251310
0.8056	Intermediate Similarity	NPC251139
0.8051	Intermediate Similarity	NPC470975
0.8051	Intermediate Similarity	NPC470979
0.8051	Intermediate Similarity	NPC103088
0.8047	Intermediate Similarity	NPC470973
0.8047	Intermediate Similarity	NPC225049
0.8034	Intermediate Similarity	NPC475945
0.8034	Intermediate Similarity	NPC475871
0.8033	Intermediate Similarity	NPC46269
0.8033	Intermediate Similarity	NPC106395
0.8031	Intermediate Similarity	NPC67251
0.803	Intermediate Similarity	NPC476823
0.8017	Intermediate Similarity	NPC317107
0.8017	Intermediate Similarity	NPC304180
0.8017	Intermediate Similarity	NPC179798
0.8016	Intermediate Similarity	NPC4021
0.8016	Intermediate Similarity	NPC159456
0.8016	Intermediate Similarity	NPC67569
0.8	Intermediate Similarity	NPC473636
0.8	Intermediate Similarity	NPC470851
0.8	Intermediate Similarity	NPC473839
0.8	Intermediate Similarity	NPC471934
0.8	Intermediate Similarity	NPC470880
0.8	Intermediate Similarity	NPC77689
0.8	Intermediate Similarity	NPC211093
0.8	Intermediate Similarity	NPC163004
0.8	Intermediate Similarity	NPC221414
0.7984	Intermediate Similarity	NPC471145
0.7984	Intermediate Similarity	NPC476712
0.7984	Intermediate Similarity	NPC470882
0.7984	Intermediate Similarity	NPC296822
0.7984	Intermediate Similarity	NPC474518
0.7984	Intermediate Similarity	NPC476713
0.7984	Intermediate Similarity	NPC473253
0.7984	Intermediate Similarity	NPC471146
0.7983	Intermediate Similarity	NPC469558
0.7969	Intermediate Similarity	NPC470922
0.7969	Intermediate Similarity	NPC8369
0.7969	Intermediate Similarity	NPC476729
0.7969	Intermediate Similarity	NPC24651
0.7955	Intermediate Similarity	NPC469673
0.7955	Intermediate Similarity	NPC469674
0.7953	Intermediate Similarity	NPC269642
0.7953	Intermediate Similarity	NPC222688
0.7951	Intermediate Similarity	NPC123855
0.7951	Intermediate Similarity	NPC473877
0.7951	Intermediate Similarity	NPC138757
0.7951	Intermediate Similarity	NPC76550
0.7949	Intermediate Similarity	NPC474747
0.7939	Intermediate Similarity	NPC476862
0.7939	Intermediate Similarity	NPC476855
0.7939	Intermediate Similarity	NPC471170
0.7939	Intermediate Similarity	NPC476863
0.7939	Intermediate Similarity	NPC196921
0.7939	Intermediate Similarity	NPC220757
0.7937	Intermediate Similarity	NPC142882
0.7937	Intermediate Similarity	NPC4548
0.7937	Intermediate Similarity	NPC268530
0.7937	Intermediate Similarity	NPC251226
0.7937	Intermediate Similarity	NPC154491
0.7934	Intermediate Similarity	NPC5103
0.7923	Intermediate Similarity	NPC476859
0.7923	Intermediate Similarity	NPC470850
0.792	Intermediate Similarity	NPC478206
0.792	Intermediate Similarity	NPC257457
0.792	Intermediate Similarity	NPC108581
0.792	Intermediate Similarity	NPC186525
0.792	Intermediate Similarity	NPC311554
0.792	Intermediate Similarity	NPC478205

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 NPC471940 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	1716
0.2-0.3	3565
0.3-0.4	2319
0.4-0.5	855
0.5-0.6	352
0.6-0.7	102
0.7-0.8	10
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7833	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD6371	Approved
0.7712	Intermediate Similarity	NPD5344	Discontinued
0.7698	Intermediate Similarity	NPD7115	Discovery
0.7627	Intermediate Similarity	NPD6648	Approved
0.7623	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD6319	Approved
0.7381	Intermediate Similarity	NPD8297	Approved
0.7328	Intermediate Similarity	NPD8516	Approved
0.7328	Intermediate Similarity	NPD8517	Approved
0.7328	Intermediate Similarity	NPD8513	Phase 3
0.7328	Intermediate Similarity	NPD8515	Approved
0.7328	Intermediate Similarity	NPD7983	Approved
0.728	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7838	Discovery
0.7222	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD7319	Approved
0.7188	Intermediate Similarity	NPD4632	Approved
0.7165	Intermediate Similarity	NPD6650	Approved
0.7165	Intermediate Similarity	NPD6649	Approved
0.7164	Intermediate Similarity	NPD7492	Approved
0.7132	Intermediate Similarity	NPD7736	Approved
0.7121	Intermediate Similarity	NPD6054	Approved
0.7111	Intermediate Similarity	NPD6616	Approved
0.7107	Intermediate Similarity	NPD4225	Approved
0.7094	Intermediate Similarity	NPD46	Approved
0.7094	Intermediate Similarity	NPD6698	Approved
0.7068	Intermediate Similarity	NPD6921	Approved
0.7063	Intermediate Similarity	NPD6881	Approved
0.7063	Intermediate Similarity	NPD6899	Approved
0.7059	Intermediate Similarity	NPD8074	Phase 3
0.7059	Intermediate Similarity	NPD7078	Approved
0.7031	Intermediate Similarity	NPD8130	Phase 1
0.7015	Intermediate Similarity	NPD6370	Approved
0.7008	Intermediate Similarity	NPD6373	Approved
0.7008	Intermediate Similarity	NPD6372	Approved
0.7	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7507	Approved
0.6984	Remote Similarity	NPD5697	Approved
0.6984	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6882	Approved
0.6975	Remote Similarity	NPD5778	Approved
0.6975	Remote Similarity	NPD5779	Approved
0.6963	Remote Similarity	NPD8328	Phase 3
0.6963	Remote Similarity	NPD7604	Phase 2
0.6953	Remote Similarity	NPD4634	Approved
0.6953	Remote Similarity	NPD6883	Approved
0.6953	Remote Similarity	NPD7290	Approved
0.6953	Remote Similarity	NPD7102	Approved
0.694	Remote Similarity	NPD6016	Approved
0.694	Remote Similarity	NPD6015	Approved
0.6934	Remote Similarity	NPD8293	Discontinued
0.6905	Remote Similarity	NPD6675	Approved
0.6905	Remote Similarity	NPD7128	Approved
0.6905	Remote Similarity	NPD5739	Approved
0.6905	Remote Similarity	NPD6402	Approved
0.6899	Remote Similarity	NPD6617	Approved
0.6899	Remote Similarity	NPD6847	Approved
0.6899	Remote Similarity	NPD6869	Approved
0.6894	Remote Similarity	NPD6009	Approved
0.6889	Remote Similarity	NPD5988	Approved
0.6875	Remote Similarity	NPD6014	Approved
0.6875	Remote Similarity	NPD6012	Approved
0.6875	Remote Similarity	NPD6013	Approved
0.6866	Remote Similarity	NPD6059	Approved
0.6846	Remote Similarity	NPD6053	Discontinued
0.6829	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5983	Phase 2
0.68	Remote Similarity	NPD5211	Phase 2
0.6797	Remote Similarity	NPD6011	Approved
0.6797	Remote Similarity	NPD7320	Approved
0.6797	Remote Similarity	NPD6686	Approved
0.6791	Remote Similarity	NPD7516	Approved
0.6774	Remote Similarity	NPD7640	Approved
0.6774	Remote Similarity	NPD7639	Approved
0.6772	Remote Similarity	NPD6008	Approved
0.6769	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6336	Discontinued
0.6738	Remote Similarity	NPD7260	Phase 2
0.6736	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD1695	Approved
0.6719	Remote Similarity	NPD5701	Approved
0.6716	Remote Similarity	NPD7328	Approved
0.6716	Remote Similarity	NPD7327	Approved
0.6694	Remote Similarity	NPD7638	Approved
0.6693	Remote Similarity	NPD5141	Approved
0.6691	Remote Similarity	NPD7503	Approved
0.6642	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.664	Remote Similarity	NPD4696	Approved
0.664	Remote Similarity	NPD5286	Approved
0.664	Remote Similarity	NPD5285	Approved
0.6619	Remote Similarity	NPD8273	Phase 1
0.6594	Remote Similarity	NPD7830	Approved
0.6594	Remote Similarity	NPD7829	Approved
0.6569	Remote Similarity	NPD8335	Approved
0.6569	Remote Similarity	NPD8379	Approved
0.6569	Remote Similarity	NPD8296	Approved
0.6569	Remote Similarity	NPD8378	Approved
0.6569	Remote Similarity	NPD8033	Approved
0.6569	Remote Similarity	NPD8380	Approved
0.6544	Remote Similarity	NPD7101	Approved
0.6544	Remote Similarity	NPD7100	Approved
0.6535	Remote Similarity	NPD5224	Approved
0.6535	Remote Similarity	NPD5225	Approved
0.6535	Remote Similarity	NPD5226	Approved
0.6535	Remote Similarity	NPD4633	Approved
0.6532	Remote Similarity	NPD7839	Suspended
0.6529	Remote Similarity	NPD5785	Approved
0.6515	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD5282	Discontinued
0.6496	Remote Similarity	NPD8294	Approved
0.6496	Remote Similarity	NPD8377	Approved
0.6484	Remote Similarity	NPD5175	Approved
0.6484	Remote Similarity	NPD5174	Approved
0.648	Remote Similarity	NPD4755	Approved
0.6475	Remote Similarity	NPD7642	Approved
0.6475	Remote Similarity	NPD7637	Suspended
0.6471	Remote Similarity	NPD6335	Approved
0.6457	Remote Similarity	NPD5223	Approved
0.6457	Remote Similarity	NPD1700	Approved
0.6446	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6101	Approved
0.6444	Remote Similarity	NPD6274	Approved
0.6433	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD8133	Approved
0.6412	Remote Similarity	NPD4729	Approved
0.6412	Remote Similarity	NPD4730	Approved
0.6408	Remote Similarity	NPD6033	Approved
0.6397	Remote Similarity	NPD6317	Approved
0.6387	Remote Similarity	NPD5363	Approved
0.6387	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD4700	Approved
0.6364	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.635	Remote Similarity	NPD6313	Approved
0.635	Remote Similarity	NPD6314	Approved
0.6349	Remote Similarity	NPD6083	Phase 2
0.6349	Remote Similarity	NPD6084	Phase 2
0.6345	Remote Similarity	NPD6845	Suspended
0.6341	Remote Similarity	NPD6411	Approved
0.6333	Remote Similarity	NPD5786	Approved
0.6331	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5248	Approved
0.6316	Remote Similarity	NPD5250	Approved
0.6316	Remote Similarity	NPD5247	Approved
0.6316	Remote Similarity	NPD5249	Phase 3
0.6316	Remote Similarity	NPD5251	Approved
0.6301	Remote Similarity	NPD8434	Phase 2
0.6294	Remote Similarity	NPD8368	Discontinued
0.6279	Remote Similarity	NPD8407	Phase 2
0.6279	Remote Similarity	NPD7632	Discontinued
0.627	Remote Similarity	NPD5222	Approved
0.627	Remote Similarity	NPD5221	Approved
0.627	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD8451	Approved
0.626	Remote Similarity	NPD4768	Approved
0.626	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD7799	Discontinued
0.625	Remote Similarity	NPD1696	Phase 3
0.6233	Remote Similarity	NPD8338	Approved
0.6224	Remote Similarity	NPD8448	Approved
0.622	Remote Similarity	NPD5173	Approved
0.622	Remote Similarity	NPD7902	Approved
0.6216	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6909	Approved
0.6214	Remote Similarity	NPD8444	Approved
0.6214	Remote Similarity	NPD6908	Approved
0.6212	Remote Similarity	NPD6412	Phase 2
0.621	Remote Similarity	NPD6079	Approved
0.6204	Remote Similarity	NPD6868	Approved
0.6197	Remote Similarity	NPD8342	Approved
0.6197	Remote Similarity	NPD8299	Approved
0.6197	Remote Similarity	NPD8340	Approved
0.6197	Remote Similarity	NPD8341	Approved
0.619	Remote Similarity	NPD5695	Phase 3
0.6172	Remote Similarity	NPD5696	Approved
0.6165	Remote Similarity	NPD5128	Approved
0.616	Remote Similarity	NPD6399	Phase 3
0.6154	Remote Similarity	NPD7236	Approved
0.6149	Remote Similarity	NPD8415	Approved
0.6148	Remote Similarity	NPD5215	Approved
0.6148	Remote Similarity	NPD5217	Approved
0.6148	Remote Similarity	NPD7524	Approved
0.6148	Remote Similarity	NPD5216	Approved
0.6142	Remote Similarity	NPD4697	Phase 3
0.6136	Remote Similarity	NPD8360	Approved
0.6136	Remote Similarity	NPD8361	Approved
0.6134	Remote Similarity	NPD4269	Approved
0.6134	Remote Similarity	NPD4270	Approved
0.6116	Remote Similarity	NPD1694	Approved
0.6115	Remote Similarity	NPD7641	Discontinued
0.6111	Remote Similarity	NPD7748	Approved
0.6107	Remote Similarity	NPD4754	Approved
0.6096	Remote Similarity	NPD8391	Approved
0.6096	Remote Similarity	NPD8392	Approved
0.6096	Remote Similarity	NPD8390	Approved
0.6083	Remote Similarity	NPD7154	Phase 3
0.6083	Remote Similarity	NPD6110	Phase 1
0.6083	Remote Similarity	NPD5362	Discontinued
0.608	Remote Similarity	NPD5281	Approved
0.608	Remote Similarity	NPD5284	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