NPASS Compound

Structure

NPC472079 OpenBabel07101718282D 47 53 0 0 1 0 0 0 0 0999 V2000 2.6126 -1.2801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6306 0.1212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2202 -2.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6739 -3.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7543 -3.0257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2543 -3.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7847 -1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -3.2007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3883 -2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5223 -1.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3883 -5.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5223 -4.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -1.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7902 -3.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7184 -4.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6562 -4.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7171 -0.2856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8135 -1.8271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8079 -3.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7184 -3.8917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3883 -3.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6562 -2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2543 -4.8917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9242 -3.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1810 -1.7226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8524 -3.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9864 -3.8917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9081 0.3022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9864 -4.8917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2543 -3.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7902 -1.8917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9242 -2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5223 -3.8917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6562 -3.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8079 -2.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5844 -3.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8524 -2.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1203 -3.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0126 1.2967 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0991 0.8900 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8524 -5.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0582 -3.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1203 -5.3917 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 18 1 0 0 0 0 2 18 1 0 0 0 0 4 20 1 0 0 0 0 5 32 1 0 0 0 0 6 32 1 0 0 0 0 7 33 1 0 0 0 0 9 10 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 35 1 0 0 0 0 13 19 1 0 0 0 0 13 37 1 0 0 0 0 14 33 1 0 0 0 0 15 26 1 0 0 0 0 16 21 1 0 0 0 0 16 44 1 0 0 0 0 17 35 1 0 0 0 0 17 36 1 0 0 0 0 18 30 1 0 0 0 0 19 3 1 1 0 0 0 19 27 1 0 0 0 0 20 38 2 0 0 0 0 20 45 1 0 0 0 0 21 28 1 0 0 0 0 21 39 1 1 0 0 0 22 14 1 6 0 0 0 22 27 1 0 0 0 0 22 47 1 0 0 0 0 23 32 1 0 0 0 0 23 35 1 6 0 0 0 24 33 1 1 0 0 0 24 36 1 0 0 0 0 25 32 1 0 0 0 0 25 46 1 6 0 0 0 26 34 1 6 0 0 0 26 45 1 0 0 0 0 27 34 1 6 0 0 0 28 29 1 0 0 0 0 28 40 1 6 0 0 0 29 31 1 0 0 0 0 29 41 1 1 0 0 0 30 37 1 0 0 0 0 30 42 2 0 0 0 0 31 44 1 0 0 0 0 31 46 1 6 0 0 0 33 34 1 1 0 0 0 34 8 1 6 0 0 0 35 36 1 1 0 0 0 36 15 1 1 0 0 0 37 43 1 1 0 0 0 37 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	662.4
Volume:	671.242
LogP:	4.229
LogD:	4.176
LogS:	-4.367
# Rotatable Bonds:	6
TPSA:	151.98
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.253
Synthetic Accessibility Score:	6.574
Fsp3:	0.946
Lipinski Rule-of-5:	Accepted
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:	-5.237
MDCK Permeability:	3.575565278879367e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.253

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	91.73326110839844%
Volume Distribution (VD):	0.82
Pgp-substrate:	7.686494827270508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.496
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.768
CYP2C9-inhibitor:	0.094
CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.706
CYP3A4-substrate:	0.539

ADMET: Excretion

Clearance (CL):	2.048
Half-life (T1/2):	0.518

ADMET: Toxicity

hERG Blockers:	0.596
Human Hepatotoxicity (H-HT):	0.347
Drug-inuced Liver Injury (DILI):	0.252
AMES Toxicity:	0.057
Rat Oral Acute Toxicity:	0.566
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.481
Carcinogencity:	0.143
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC472079

Natural Product ID:	NPC472079
*Common Name:**	BAGZDYNMKJFRBA-JNRIXAQASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BAGZDYNMKJFRBA-JNRIXAQASA-N
Standard InCHI:	InChI=1S/C37H58O10/c1-18(2)30(42)37(43)13-19(3)27-22(47-37)14-33(7)24-10-9-23-32(5,6)25(46-31-29(41)28(40)21(39)16-44-31)11-12-35(23)17-36(24,35)15-26(34(27,33)8)45-20(4)38/h18-19,21-29,31,39-41,43H,9-17H2,1-8H3/t19-,21-,22+,23+,24+,25+,26-,27+,28+,29-,31+,33+,34-,35-,36+,37+/m1/s1
SMILES:	CC1CC(OC2C1C3(C(CC45CC46CCC(C(C6CCC5C3(C2)C)(C)C)OC7C(C(C(CO7)O)O)O)OC(=O)C)C)(C(=O)C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3337549
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins [CHEMONTID:0001687] Cucurbitacin glycosides

*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
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	n.a.	aerial part	n.a.	PMID[19280146]
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	rhizomes	n.a.	n.a.	PMID[25136911]
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	5

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[483366]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[483366]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[483366]

☑ 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 NPC472079 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	577
0.1-0.2	4089
0.2-0.3	10553
0.3-0.4	12218
0.4-0.5	6426
0.5-0.6	4391
0.6-0.7	2521
0.7-0.8	1653
0.8-0.85	216
0.85-0.9	43
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9293	High Similarity	NPC41843
0.9135	High Similarity	NPC227879
0.9135	High Similarity	NPC208333
0.9126	High Similarity	NPC203974
0.91	High Similarity	NPC20028
0.901	High Similarity	NPC477172
0.8952	High Similarity	NPC228190
0.8952	High Similarity	NPC236753
0.8922	High Similarity	NPC310031
0.8922	High Similarity	NPC80191
0.8879	High Similarity	NPC477489
0.8824	High Similarity	NPC108227
0.8824	High Similarity	NPC476512
0.8824	High Similarity	NPC472081
0.8824	High Similarity	NPC476838
0.8824	High Similarity	NPC476839
0.88	High Similarity	NPC296936
0.8785	High Similarity	NPC473062
0.875	High Similarity	NPC469827
0.8738	High Similarity	NPC310138
0.8738	High Similarity	NPC114700
0.8738	High Similarity	NPC134967
0.8738	High Similarity	NPC470029
0.8727	High Similarity	NPC179429
0.8713	High Similarity	NPC470591
0.8713	High Similarity	NPC472273
0.87	High Similarity	NPC215570
0.8687	High Similarity	NPC473726
0.8667	High Similarity	NPC215408
0.8654	High Similarity	NPC97260
0.8654	High Similarity	NPC139181
0.8654	High Similarity	NPC476837
0.8611	High Similarity	NPC469824
0.86	High Similarity	NPC151214
0.86	High Similarity	NPC191915
0.8598	High Similarity	NPC469825
0.8532	High Similarity	NPC477492
0.8529	High Similarity	NPC210157
0.8515	High Similarity	NPC57964
0.8515	High Similarity	NPC94582
0.8505	High Similarity	NPC469826
0.8505	High Similarity	NPC202898
0.8505	High Similarity	NPC92890
0.8505	High Similarity	NPC475319
0.8485	Intermediate Similarity	NPC65550
0.8476	Intermediate Similarity	NPC107385
0.8476	Intermediate Similarity	NPC34562
0.8462	Intermediate Similarity	NPC475574
0.8431	Intermediate Similarity	NPC238796
0.8431	Intermediate Similarity	NPC252056
0.8431	Intermediate Similarity	NPC203434
0.8431	Intermediate Similarity	NPC142264
0.8431	Intermediate Similarity	NPC476510
0.8431	Intermediate Similarity	NPC237071
0.8426	Intermediate Similarity	NPC220836
0.8426	Intermediate Similarity	NPC94086
0.8426	Intermediate Similarity	NPC233433
0.8426	Intermediate Similarity	NPC473844
0.8426	Intermediate Similarity	NPC273002
0.8426	Intermediate Similarity	NPC51947
0.8426	Intermediate Similarity	NPC92297
0.8426	Intermediate Similarity	NPC473817
0.84	Intermediate Similarity	NPC473830
0.84	Intermediate Similarity	NPC204881
0.8396	Intermediate Similarity	NPC470167
0.8381	Intermediate Similarity	NPC470172
0.8365	Intermediate Similarity	NPC470030
0.835	Intermediate Similarity	NPC475207
0.835	Intermediate Similarity	NPC233649
0.835	Intermediate Similarity	NPC470028
0.8333	Intermediate Similarity	NPC88744
0.8317	Intermediate Similarity	NPC88962
0.8317	Intermediate Similarity	NPC144790
0.8317	Intermediate Similarity	NPC149400
0.8317	Intermediate Similarity	NPC172838
0.8317	Intermediate Similarity	NPC137004
0.8302	Intermediate Similarity	NPC473406
0.8288	Intermediate Similarity	NPC73986
0.8288	Intermediate Similarity	NPC97002
0.8283	Intermediate Similarity	NPC281004
0.8273	Intermediate Similarity	NPC275668
0.8273	Intermediate Similarity	NPC91838
0.8273	Intermediate Similarity	NPC11035
0.8273	Intermediate Similarity	NPC1876
0.8273	Intermediate Similarity	NPC240734
0.8273	Intermediate Similarity	NPC204392
0.8257	Intermediate Similarity	NPC240125
0.8257	Intermediate Similarity	NPC91583
0.8252	Intermediate Similarity	NPC156377
0.8235	Intermediate Similarity	NPC252253
0.8235	Intermediate Similarity	NPC174024
0.8235	Intermediate Similarity	NPC291547
0.8235	Intermediate Similarity	NPC24960
0.8235	Intermediate Similarity	NPC45959
0.8235	Intermediate Similarity	NPC179859
0.8235	Intermediate Similarity	NPC475436
0.8235	Intermediate Similarity	NPC473774
0.8235	Intermediate Similarity	NPC312678
0.8235	Intermediate Similarity	NPC175
0.8235	Intermediate Similarity	NPC253268
0.8235	Intermediate Similarity	NPC131693
0.8235	Intermediate Similarity	NPC309866
0.8235	Intermediate Similarity	NPC473851
0.823	Intermediate Similarity	NPC156651
0.8214	Intermediate Similarity	NPC79193
0.8208	Intermediate Similarity	NPC80640
0.82	Intermediate Similarity	NPC102725
0.82	Intermediate Similarity	NPC131466
0.82	Intermediate Similarity	NPC473472
0.8198	Intermediate Similarity	NPC470543
0.8198	Intermediate Similarity	NPC243572
0.8174	Intermediate Similarity	NPC170814
0.8173	Intermediate Similarity	NPC471241
0.8155	Intermediate Similarity	NPC473067
0.8155	Intermediate Similarity	NPC305808
0.8155	Intermediate Similarity	NPC92196
0.8155	Intermediate Similarity	NPC473064
0.8155	Intermediate Similarity	NPC473065
0.8137	Intermediate Similarity	NPC297348
0.8137	Intermediate Similarity	NPC249204
0.8137	Intermediate Similarity	NPC177834
0.8137	Intermediate Similarity	NPC477547
0.8137	Intermediate Similarity	NPC141769
0.8137	Intermediate Similarity	NPC234352
0.8137	Intermediate Similarity	NPC250393
0.8137	Intermediate Similarity	NPC48339
0.8137	Intermediate Similarity	NPC477451
0.8137	Intermediate Similarity	NPC325828
0.8136	Intermediate Similarity	NPC273962
0.8131	Intermediate Similarity	NPC471253
0.8125	Intermediate Similarity	NPC102619
0.8125	Intermediate Similarity	NPC146563
0.8119	Intermediate Similarity	NPC473542
0.8119	Intermediate Similarity	NPC279329
0.8119	Intermediate Similarity	NPC77756
0.8119	Intermediate Similarity	NPC223143
0.8108	Intermediate Similarity	NPC274833
0.8103	Intermediate Similarity	NPC470478
0.8077	Intermediate Similarity	NPC121453
0.8077	Intermediate Similarity	NPC304011
0.8077	Intermediate Similarity	NPC139271
0.8077	Intermediate Similarity	NPC476728
0.8073	Intermediate Similarity	NPC287269
0.8073	Intermediate Similarity	NPC126753
0.8058	Intermediate Similarity	NPC264101
0.8058	Intermediate Similarity	NPC222731
0.8058	Intermediate Similarity	NPC471464
0.8058	Intermediate Similarity	NPC291203
0.8058	Intermediate Similarity	NPC294686
0.8058	Intermediate Similarity	NPC217205
0.8056	Intermediate Similarity	NPC267637
0.8053	Intermediate Similarity	NPC54395
0.8053	Intermediate Similarity	NPC469821
0.8039	Intermediate Similarity	NPC210759
0.8039	Intermediate Similarity	NPC36372
0.8039	Intermediate Similarity	NPC293609
0.8039	Intermediate Similarity	NPC307167
0.8039	Intermediate Similarity	NPC476668
0.8039	Intermediate Similarity	NPC229801
0.8039	Intermediate Similarity	NPC473637
0.8039	Intermediate Similarity	NPC149966
0.8039	Intermediate Similarity	NPC5632
0.8037	Intermediate Similarity	NPC94919
0.8036	Intermediate Similarity	NPC472719
0.8036	Intermediate Similarity	NPC477253
0.8036	Intermediate Similarity	NPC207845
0.8019	Intermediate Similarity	NPC80417
0.8018	Intermediate Similarity	NPC470622
0.8017	Intermediate Similarity	NPC471406
0.8	Intermediate Similarity	NPC307534
0.8	Intermediate Similarity	NPC43912
0.8	Intermediate Similarity	NPC477223
0.8	Intermediate Similarity	NPC239293
0.8	Intermediate Similarity	NPC477222
0.8	Intermediate Similarity	NPC207693
0.8	Intermediate Similarity	NPC476112
0.8	Intermediate Similarity	NPC140446
0.7982	Intermediate Similarity	NPC469820
0.7982	Intermediate Similarity	NPC469823
0.7982	Intermediate Similarity	NPC475490
0.7982	Intermediate Similarity	NPC137414
0.7982	Intermediate Similarity	NPC273189
0.7982	Intermediate Similarity	NPC184805
0.7981	Intermediate Similarity	NPC107188
0.7981	Intermediate Similarity	NPC211354
0.7981	Intermediate Similarity	NPC19400
0.7981	Intermediate Similarity	NPC474399
0.7981	Intermediate Similarity	NPC473610
0.7981	Intermediate Similarity	NPC6295
0.7981	Intermediate Similarity	NPC107962
0.7981	Intermediate Similarity	NPC206003
0.7981	Intermediate Similarity	NPC473727
0.7981	Intermediate Similarity	NPC470031
0.7981	Intermediate Similarity	NPC475351
0.7961	Intermediate Similarity	NPC311246
0.7961	Intermediate Similarity	NPC277774
0.7961	Intermediate Similarity	NPC476669
0.7961	Intermediate Similarity	NPC167644
0.7949	Intermediate Similarity	NPC47567
0.7949	Intermediate Similarity	NPC412

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 NPC472079 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	605
0.1-0.2	3949
0.2-0.3	3128
0.3-0.4	810
0.4-0.5	337
0.5-0.6	203
0.6-0.7	99
0.7-0.8	16
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD8170	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD8171	Discontinued
0.7965	Intermediate Similarity	NPD8133	Approved
0.7759	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD8328	Phase 3
0.7419	Intermediate Similarity	NPD7736	Approved
0.7281	Intermediate Similarity	NPD6412	Phase 2
0.7273	Intermediate Similarity	NPD6118	Approved
0.7273	Intermediate Similarity	NPD8294	Approved
0.7273	Intermediate Similarity	NPD6114	Approved
0.7273	Intermediate Similarity	NPD6697	Approved
0.7273	Intermediate Similarity	NPD6115	Approved
0.7273	Intermediate Similarity	NPD8377	Approved
0.7258	Intermediate Similarity	NPD7507	Approved
0.7227	Intermediate Similarity	NPD6940	Discontinued
0.7213	Intermediate Similarity	NPD8378	Approved
0.7213	Intermediate Similarity	NPD8033	Approved
0.7213	Intermediate Similarity	NPD8380	Approved
0.7213	Intermediate Similarity	NPD8379	Approved
0.7213	Intermediate Similarity	NPD8296	Approved
0.7213	Intermediate Similarity	NPD8335	Approved
0.72	Intermediate Similarity	NPD8293	Discontinued
0.7172	Intermediate Similarity	NPD6116	Phase 1
0.7129	Intermediate Similarity	NPD6928	Phase 2
0.7087	Intermediate Similarity	NPD7319	Approved
0.7071	Intermediate Similarity	NPD6117	Approved
0.7016	Intermediate Similarity	NPD6370	Approved
0.6975	Remote Similarity	NPD6882	Approved
0.6975	Remote Similarity	NPD8297	Approved
0.6967	Remote Similarity	NPD7328	Approved
0.6967	Remote Similarity	NPD7327	Approved
0.6911	Remote Similarity	NPD7516	Approved
0.6905	Remote Similarity	NPD7492	Approved
0.6885	Remote Similarity	NPD6009	Approved
0.6869	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6319	Approved
0.6855	Remote Similarity	NPD6054	Approved
0.6855	Remote Similarity	NPD6059	Approved
0.685	Remote Similarity	NPD6616	Approved
0.6842	Remote Similarity	NPD1700	Approved
0.6797	Remote Similarity	NPD7078	Approved
0.6762	Remote Similarity	NPD3669	Approved
0.6762	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6675	Approved
0.6752	Remote Similarity	NPD7128	Approved
0.6752	Remote Similarity	NPD6402	Approved
0.6752	Remote Similarity	NPD5739	Approved
0.6727	Remote Similarity	NPD8034	Phase 2
0.6727	Remote Similarity	NPD8035	Phase 2
0.6723	Remote Similarity	NPD6373	Approved
0.6723	Remote Similarity	NPD6372	Approved
0.6693	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5777	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4632	Approved
0.6639	Remote Similarity	NPD6686	Approved
0.6639	Remote Similarity	NPD6881	Approved
0.6639	Remote Similarity	NPD7320	Approved
0.6639	Remote Similarity	NPD6899	Approved
0.6634	Remote Similarity	NPD3703	Phase 2
0.6634	Remote Similarity	NPD3702	Approved
0.6614	Remote Similarity	NPD5988	Approved
0.6612	Remote Similarity	NPD6649	Approved
0.6612	Remote Similarity	NPD8130	Phase 1
0.6612	Remote Similarity	NPD6650	Approved
0.6571	Remote Similarity	NPD1779	Approved
0.6571	Remote Similarity	NPD1780	Approved
0.6566	Remote Similarity	NPD4244	Approved
0.6566	Remote Similarity	NPD4245	Approved
0.6566	Remote Similarity	NPD4789	Approved
0.6555	Remote Similarity	NPD5697	Approved
0.6555	Remote Similarity	NPD5701	Approved
0.6529	Remote Similarity	NPD7290	Approved
0.6529	Remote Similarity	NPD6883	Approved
0.6529	Remote Similarity	NPD7102	Approved
0.6481	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6847	Approved
0.6475	Remote Similarity	NPD6869	Approved
0.6475	Remote Similarity	NPD6617	Approved
0.6465	Remote Similarity	NPD3698	Phase 2
0.6465	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6014	Approved
0.6446	Remote Similarity	NPD6013	Approved
0.6446	Remote Similarity	NPD6012	Approved
0.6435	Remote Similarity	NPD6084	Phase 2
0.6435	Remote Similarity	NPD6083	Phase 2
0.6406	Remote Similarity	NPD5983	Phase 2
0.6404	Remote Similarity	NPD7991	Discontinued
0.6364	Remote Similarity	NPD6011	Approved
0.6364	Remote Similarity	NPD6033	Approved
0.6341	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6081	Approved
0.6336	Remote Similarity	NPD6336	Discontinued
0.6308	Remote Similarity	NPD6067	Discontinued
0.63	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7638	Approved
0.6214	Remote Similarity	NPD1810	Approved
0.6214	Remote Similarity	NPD1811	Approved
0.62	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5360	Phase 3
0.6186	Remote Similarity	NPD7639	Approved
0.6186	Remote Similarity	NPD8418	Phase 2
0.6186	Remote Similarity	NPD7640	Approved
0.6179	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD7748	Approved
0.6162	Remote Similarity	NPD4224	Phase 2
0.6154	Remote Similarity	NPD8517	Approved
0.6154	Remote Similarity	NPD6921	Approved
0.6154	Remote Similarity	NPD8516	Approved
0.6154	Remote Similarity	NPD7902	Approved
0.6154	Remote Similarity	NPD4755	Approved
0.6154	Remote Similarity	NPD8515	Approved
0.6154	Remote Similarity	NPD8513	Phase 3
0.6142	Remote Similarity	NPD6274	Approved
0.6132	Remote Similarity	NPD4238	Approved
0.6132	Remote Similarity	NPD4802	Phase 2
0.6129	Remote Similarity	NPD4634	Approved
0.6124	Remote Similarity	NPD7100	Approved
0.6124	Remote Similarity	NPD7101	Approved
0.6121	Remote Similarity	NPD5695	Phase 3
0.6102	Remote Similarity	NPD5696	Approved
0.6094	Remote Similarity	NPD7115	Discovery
0.6087	Remote Similarity	NPD6399	Phase 3
0.6083	Remote Similarity	NPD8086	Approved
0.6083	Remote Similarity	NPD8083	Approved
0.6083	Remote Similarity	NPD8082	Approved
0.6083	Remote Similarity	NPD8138	Approved
0.6083	Remote Similarity	NPD8085	Approved
0.6083	Remote Similarity	NPD8139	Approved
0.6083	Remote Similarity	NPD8084	Approved
0.6083	Remote Similarity	NPD7632	Discontinued
0.608	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7329	Approved
0.6066	Remote Similarity	NPD6008	Approved
0.6061	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.605	Remote Similarity	NPD4700	Approved
0.605	Remote Similarity	NPD5286	Approved
0.605	Remote Similarity	NPD5285	Approved
0.605	Remote Similarity	NPD4696	Approved
0.6047	Remote Similarity	NPD6335	Approved
0.6033	Remote Similarity	NPD8276	Approved
0.6033	Remote Similarity	NPD8275	Approved
0.6031	Remote Similarity	NPD6909	Approved
0.6031	Remote Similarity	NPD6908	Approved
0.6	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7515	Phase 2
0.5984	Remote Similarity	NPD8081	Approved
0.5981	Remote Similarity	NPD3671	Phase 1
0.5969	Remote Similarity	NPD6317	Approved
0.5968	Remote Similarity	NPD8174	Phase 2
0.595	Remote Similarity	NPD5211	Phase 2
0.595	Remote Similarity	NPD8301	Approved
0.595	Remote Similarity	NPD8300	Approved
0.595	Remote Similarity	NPD5225	Approved
0.595	Remote Similarity	NPD5226	Approved
0.595	Remote Similarity	NPD4633	Approved
0.595	Remote Similarity	NPD5224	Approved
0.5935	Remote Similarity	NPD4767	Approved
0.5935	Remote Similarity	NPD4768	Approved
0.5935	Remote Similarity	NPD8393	Approved
0.5923	Remote Similarity	NPD6313	Approved
0.5923	Remote Similarity	NPD6314	Approved
0.5922	Remote Similarity	NPD2687	Approved
0.5922	Remote Similarity	NPD2686	Approved
0.5922	Remote Similarity	NPD2254	Approved
0.5912	Remote Similarity	NPD5956	Approved
0.5902	Remote Similarity	NPD5174	Approved
0.5902	Remote Similarity	NPD5175	Approved
0.5897	Remote Similarity	NPD7900	Approved
0.5897	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD5737	Approved
0.5877	Remote Similarity	NPD6672	Approved
0.5868	Remote Similarity	NPD5223	Approved
0.5865	Remote Similarity	NPD4758	Discontinued
0.5856	Remote Similarity	NPD4788	Approved
0.5854	Remote Similarity	NPD5141	Approved
0.585	Remote Similarity	NPD7625	Phase 1
0.5847	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6098	Approved
0.584	Remote Similarity	NPD4730	Approved
0.584	Remote Similarity	NPD4729	Approved
0.5833	Remote Similarity	NPD5364	Discontinued
0.5827	Remote Similarity	NPD8449	Approved
0.5826	Remote Similarity	NPD6080	Approved
0.5826	Remote Similarity	NPD6673	Approved
0.5826	Remote Similarity	NPD4753	Phase 2
0.5826	Remote Similarity	NPD6904	Approved
0.5812	Remote Similarity	NPD4202	Approved
0.5789	Remote Similarity	NPD8274	Clinical (unspecified phase)

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