NPASS Compound

Structure

CID198714 OpenBabel06191715582D 48 53 0 0 1 0 0 0 0 0999 V2000 3.2666 -3.7999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1074 -3.3147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6641 1.0314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8996 0.4225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4745 -0.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2291 0.9694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6336 -2.8289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8168 -2.3573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2667 -0.9426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2577 2.0227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6325 -0.9425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8168 0.4716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6000 1.5064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4504 -2.3573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4504 -1.4142 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0829 -1.4142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6325 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5427 1.5063 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8168 -1.4142 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3182 2.0936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6336 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7880 1.2439 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0141 2.3227 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9568 2.3227 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4281 1.5063 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8168 0.4716 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0829 -2.3574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9567 0.6899 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2666 -2.8289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7545 1.3890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9426 0.0000 C 0 0 2 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 1.6336 -0.9426 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6769 1.4033 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1287 2.3227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9616 3.0037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4683 0.4818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5428 3.1391 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4281 3.1390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3707 1.5062 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9176 -2.8391 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1121 2.2987 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0125 2.1202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5097 0.3437 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8993 -0.9429 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0140 0.6899 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 31 1 0 0 0 0 2 31 1 0 0 0 0 3 32 1 0 0 0 0 4 32 1 0 0 0 0 5 33 1 0 0 0 0 9 10 1 0 0 0 0 9 16 2 0 0 0 0 10 21 1 0 0 0 0 11 17 1 0 0 0 0 11 18 2 0 0 0 0 12 22 1 0 0 0 0 12 24 1 0 0 0 0 13 33 1 0 0 0 0 14 23 1 0 0 0 0 14 34 1 0 0 0 0 15 37 1 0 0 0 0 16 17 1 0 0 0 0 16 31 1 0 0 0 0 17 35 1 6 0 0 0 18 29 1 0 0 0 0 18 47 1 0 0 0 0 19 13 1 1 0 0 0 19 28 1 0 0 0 0 19 46 1 0 0 0 0 20 15 1 6 0 0 0 20 25 1 0 0 0 0 20 48 1 0 0 0 0 21 33 1 1 0 0 0 21 35 1 0 0 0 0 22 36 1 0 0 0 0 22 38 2 0 0 0 0 23 35 1 0 0 0 0 23 39 2 0 0 0 0 24 32 1 6 0 0 0 24 46 1 0 0 0 0 25 26 1 0 0 0 0 25 40 1 1 0 0 0 26 27 1 0 0 0 0 26 41 1 6 0 0 0 27 30 1 0 0 0 0 27 42 1 1 0 0 0 28 34 1 6 0 0 0 28 36 1 0 0 0 0 29 31 1 0 0 0 0 29 43 2 0 0 0 0 30 47 1 6 0 0 0 30 48 1 0 0 0 0 32 44 1 0 0 0 0 33 34 1 1 0 0 0 34 6 1 6 0 0 0 35 7 1 6 0 0 0 36 8 1 1 0 0 0 36 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	676.35
Volume:	672.174
LogP:	1.773
LogD:	1.709
LogS:	-4.205
# Rotatable Bonds:	4
TPSA:	200.28
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.25
Synthetic Accessibility Score:	6.01
Fsp3:	0.806
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:	-5.323
MDCK Permeability:	1.7577784092281945e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.956
Human Intestinal Absorption (HIA):	0.742
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.933

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.239
Plasma Protein Binding (PPB):	76.80194854736328%
Volume Distribution (VD):	0.986
Pgp-substrate:	15.418630599975586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.165
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.737
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.058
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.531
CYP3A4-substrate:	0.591

ADMET: Excretion

Clearance (CL):	1.395
Half-life (T1/2):	0.667

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.168
AMES Toxicity:	0.232
Rat Oral Acute Toxicity:	0.268
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.324
Carcinogencity:	0.629
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.867

Download Data

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

Natural Product: NPC198714

Natural Product ID:	NPC198714
*Common Name:**	IWNXFVRPEIWIJJ-VPLPWDSJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IWNXFVRPEIWIJJ-VPLPWDSJSA-N
Standard InCHI:	InChI=1S/C36H52O12/c1-31(2)16-9-10-21-33(5)13-19-28(36(8,45)22(38)12-24(46-19)32(3,4)44)34(33,6)14-23(39)35(21,7)17(16)11-18(29(31)43)47-30-27(42)26(41)25(40)20(15-37)48-30/h9,11,17,19-21,24-28,30,37,40-42,44-45H,10,12-15H2,1-8H3/t17-,19-,20-,21+,24+,25-,26+,27-,28+,30-,33+,34-,35+,36+/m1/s1
SMILES:	CC1(C)C2=CC[C@H]3[C@]4(C)C[C@@H]5[C@@H]([C@@]4(C)CC(=O)[C@@]3(C)[C@@H]2C=C(C1=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)[C@](C)(C(=O)C[C@@H](C(C)(C)O)O5)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1923782
PubChem CID:	56655721
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
NPO30742	Machilus yaoshansis	Species	Lauraceae	Eukaryota	root	Dayao Mountain, Guangxi, China	2007-DEC	PMID[22044245]
NPO30742	Machilus yaoshansis	Species	Lauraceae	Eukaryota	n.a.	root	n.a.	PMID[22044245]
NPO30742	Machilus yaoshansis	Species	Lauraceae	Eukaryota	Roots	n.a.	n.a.	PMID[22779787]

☑ 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	6

Activity Type	# Activity
Cell Line	4
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	2810.0	nM	PMID[504067]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[504067]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[504067]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[504067]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[504067]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[504067]

☑ 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 NPC198714 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	275
0.1-0.2	1726
0.2-0.3	5639
0.3-0.4	9299
0.4-0.5	11409
0.5-0.6	7663
0.6-0.7	5048
0.7-0.8	1575
0.8-0.85	50
0.85-0.9	5
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9826	High Similarity	NPC1980
0.9826	High Similarity	NPC238005
0.9826	High Similarity	NPC141196
0.9652	High Similarity	NPC42675
0.9402	High Similarity	NPC216866
0.9328	High Similarity	NPC93368
0.925	High Similarity	NPC152091
0.9244	High Similarity	NPC277191
0.9244	High Similarity	NPC190846
0.9024	High Similarity	NPC213634
0.8983	High Similarity	NPC319570
0.8926	High Similarity	NPC475194
0.8862	High Similarity	NPC69273
0.8862	High Similarity	NPC168899
0.8862	High Similarity	NPC293623
0.877	High Similarity	NPC6615
0.877	High Similarity	NPC7850
0.8729	High Similarity	NPC31797
0.872	High Similarity	NPC241008
0.8696	High Similarity	NPC470257
0.8618	High Similarity	NPC30188
0.8618	High Similarity	NPC177820
0.8559	High Similarity	NPC477944
0.8525	High Similarity	NPC187950
0.8525	High Similarity	NPC278163
0.8522	High Similarity	NPC43285
0.8522	High Similarity	NPC58370
0.8468	Intermediate Similarity	NPC469841
0.8468	Intermediate Similarity	NPC469842
0.8462	Intermediate Similarity	NPC114961
0.8462	Intermediate Similarity	NPC27551
0.8455	Intermediate Similarity	NPC28532
0.843	Intermediate Similarity	NPC86020
0.843	Intermediate Similarity	NPC176005
0.843	Intermediate Similarity	NPC475632
0.8403	Intermediate Similarity	NPC260665
0.8403	Intermediate Similarity	NPC200944
0.8403	Intermediate Similarity	NPC73455
0.84	Intermediate Similarity	NPC104427
0.84	Intermediate Similarity	NPC47113
0.84	Intermediate Similarity	NPC174367
0.8376	Intermediate Similarity	NPC246205
0.8376	Intermediate Similarity	NPC304495
0.8361	Intermediate Similarity	NPC178548
0.8361	Intermediate Similarity	NPC258592
0.8359	Intermediate Similarity	NPC471855
0.8333	Intermediate Similarity	NPC292290
0.8333	Intermediate Similarity	NPC2757
0.832	Intermediate Similarity	NPC130229
0.8319	Intermediate Similarity	NPC130427
0.8306	Intermediate Similarity	NPC475431
0.8293	Intermediate Similarity	NPC475187
0.8293	Intermediate Similarity	NPC471406
0.8284	Intermediate Similarity	NPC803
0.824	Intermediate Similarity	NPC476542
0.8226	Intermediate Similarity	NPC412
0.8226	Intermediate Similarity	NPC202051
0.8226	Intermediate Similarity	NPC131841
0.8226	Intermediate Similarity	NPC169727
0.8226	Intermediate Similarity	NPC47567
0.8226	Intermediate Similarity	NPC258789
0.8226	Intermediate Similarity	NPC258815
0.8226	Intermediate Similarity	NPC241310
0.8226	Intermediate Similarity	NPC194310
0.8211	Intermediate Similarity	NPC473920
0.8211	Intermediate Similarity	NPC279143
0.8211	Intermediate Similarity	NPC161738
0.8203	Intermediate Similarity	NPC309096
0.8203	Intermediate Similarity	NPC471407
0.8203	Intermediate Similarity	NPC54614
0.8189	Intermediate Similarity	NPC305496
0.8182	Intermediate Similarity	NPC474557
0.8182	Intermediate Similarity	NPC471398
0.8182	Intermediate Similarity	NPC74727
0.8182	Intermediate Similarity	NPC116024
0.8175	Intermediate Similarity	NPC473505
0.816	Intermediate Similarity	NPC471965
0.816	Intermediate Similarity	NPC156789
0.816	Intermediate Similarity	NPC131824
0.8154	Intermediate Similarity	NPC475487
0.8151	Intermediate Similarity	NPC475317
0.8151	Intermediate Similarity	NPC154856
0.8151	Intermediate Similarity	NPC52241
0.8145	Intermediate Similarity	NPC476849
0.814	Intermediate Similarity	NPC173347
0.8136	Intermediate Similarity	NPC473288
0.8125	Intermediate Similarity	NPC245094
0.8125	Intermediate Similarity	NPC311534
0.8125	Intermediate Similarity	NPC475636
0.8125	Intermediate Similarity	NPC295220
0.812	Intermediate Similarity	NPC162033
0.812	Intermediate Similarity	NPC210178
0.811	Intermediate Similarity	NPC285091
0.8106	Intermediate Similarity	NPC141215
0.8106	Intermediate Similarity	NPC190065
0.8106	Intermediate Similarity	NPC471089
0.8095	Intermediate Similarity	NPC262199
0.8095	Intermediate Similarity	NPC471961
0.8095	Intermediate Similarity	NPC160084
0.8095	Intermediate Similarity	NPC471964
0.8095	Intermediate Similarity	NPC202666
0.8095	Intermediate Similarity	NPC228701
0.8095	Intermediate Similarity	NPC14617
0.8095	Intermediate Similarity	NPC227397
0.808	Intermediate Similarity	NPC249553
0.808	Intermediate Similarity	NPC275675
0.808	Intermediate Similarity	NPC133506
0.808	Intermediate Similarity	NPC475182
0.808	Intermediate Similarity	NPC476544
0.808	Intermediate Similarity	NPC182900
0.808	Intermediate Similarity	NPC476543
0.808	Intermediate Similarity	NPC476545
0.8067	Intermediate Similarity	NPC118225
0.8065	Intermediate Similarity	NPC127530
0.8049	Intermediate Similarity	NPC218970
0.8045	Intermediate Similarity	NPC140045
0.8045	Intermediate Similarity	NPC596
0.8045	Intermediate Similarity	NPC295885
0.8034	Intermediate Similarity	NPC223741
0.8033	Intermediate Similarity	NPC473898
0.8033	Intermediate Similarity	NPC477580
0.8033	Intermediate Similarity	NPC165439
0.8031	Intermediate Similarity	NPC471962
0.8031	Intermediate Similarity	NPC318135
0.8031	Intermediate Similarity	NPC473474
0.8031	Intermediate Similarity	NPC247315
0.8031	Intermediate Similarity	NPC473255
0.8031	Intermediate Similarity	NPC471963
0.803	Intermediate Similarity	NPC262813
0.8017	Intermediate Similarity	NPC210420
0.8017	Intermediate Similarity	NPC474265
0.8016	Intermediate Similarity	NPC313528
0.8016	Intermediate Similarity	NPC169816
0.8016	Intermediate Similarity	NPC15918
0.8016	Intermediate Similarity	NPC94072
0.8016	Intermediate Similarity	NPC305771
0.8	Intermediate Similarity	NPC129340
0.8	Intermediate Similarity	NPC472075
0.8	Intermediate Similarity	NPC472076
0.8	Intermediate Similarity	NPC474720
0.7984	Intermediate Similarity	NPC297179
0.7984	Intermediate Similarity	NPC239293
0.7984	Intermediate Similarity	NPC286347
0.7983	Intermediate Similarity	NPC272576
0.797	Intermediate Similarity	NPC251998
0.7969	Intermediate Similarity	NPC87662
0.7966	Intermediate Similarity	NPC95243
0.7966	Intermediate Similarity	NPC63023
0.7955	Intermediate Similarity	NPC478069
0.7953	Intermediate Similarity	NPC472078
0.7953	Intermediate Similarity	NPC472077
0.7951	Intermediate Similarity	NPC194100
0.7951	Intermediate Similarity	NPC178981
0.7949	Intermediate Similarity	NPC117185
0.7939	Intermediate Similarity	NPC155529
0.7939	Intermediate Similarity	NPC473805
0.7939	Intermediate Similarity	NPC473519
0.7937	Intermediate Similarity	NPC75417
0.7934	Intermediate Similarity	NPC471243
0.7923	Intermediate Similarity	NPC264192
0.7923	Intermediate Similarity	NPC476966
0.792	Intermediate Similarity	NPC214484
0.792	Intermediate Similarity	NPC469945
0.792	Intermediate Similarity	NPC473884
0.792	Intermediate Similarity	NPC39211
0.792	Intermediate Similarity	NPC35405
0.792	Intermediate Similarity	NPC157868
0.792	Intermediate Similarity	NPC475171
0.792	Intermediate Similarity	NPC309780
0.792	Intermediate Similarity	NPC11551
0.792	Intermediate Similarity	NPC180550
0.792	Intermediate Similarity	NPC114441
0.792	Intermediate Similarity	NPC208381
0.792	Intermediate Similarity	NPC472949
0.792	Intermediate Similarity	NPC6377
0.7917	Intermediate Similarity	NPC8431
0.7917	Intermediate Similarity	NPC265655
0.7907	Intermediate Similarity	NPC146456
0.7907	Intermediate Similarity	NPC469757
0.7907	Intermediate Similarity	NPC473265
0.7907	Intermediate Similarity	NPC470882
0.7907	Intermediate Similarity	NPC117702
0.7907	Intermediate Similarity	NPC471357
0.7903	Intermediate Similarity	NPC224121
0.7895	Intermediate Similarity	NPC158350
0.7895	Intermediate Similarity	NPC171619
0.7891	Intermediate Similarity	NPC248202
0.7886	Intermediate Similarity	NPC473882
0.7886	Intermediate Similarity	NPC243354
0.7886	Intermediate Similarity	NPC247069
0.7881	Intermediate Similarity	NPC121566
0.7881	Intermediate Similarity	NPC100955
0.7879	Intermediate Similarity	NPC102015
0.7874	Intermediate Similarity	NPC40775
0.7874	Intermediate Similarity	NPC249848
0.7874	Intermediate Similarity	NPC107966
0.7874	Intermediate Similarity	NPC235438
0.7874	Intermediate Similarity	NPC162574
0.7874	Intermediate Similarity	NPC275343
0.7869	Intermediate Similarity	NPC170487

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 NPC198714 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	1981
0.2-0.3	4167
0.3-0.4	1770
0.4-0.5	512
0.5-0.6	248
0.6-0.7	137
0.7-0.8	76
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8455	Intermediate Similarity	NPD6370	Approved
0.8413	Intermediate Similarity	NPD7736	Approved
0.8362	Intermediate Similarity	NPD6412	Phase 2
0.8293	Intermediate Similarity	NPD6054	Approved
0.8189	Intermediate Similarity	NPD8293	Discontinued
0.8145	Intermediate Similarity	NPD6059	Approved
0.8095	Intermediate Similarity	NPD8328	Phase 3
0.808	Intermediate Similarity	NPD6016	Approved
0.808	Intermediate Similarity	NPD6015	Approved
0.8031	Intermediate Similarity	NPD7492	Approved
0.8016	Intermediate Similarity	NPD5988	Approved
0.8	Intermediate Similarity	NPD6319	Approved
0.7969	Intermediate Similarity	NPD6616	Approved
0.7907	Intermediate Similarity	NPD7078	Approved
0.7869	Intermediate Similarity	NPD6882	Approved
0.7869	Intermediate Similarity	NPD8297	Approved
0.7786	Intermediate Similarity	NPD7319	Approved
0.776	Intermediate Similarity	NPD6009	Approved
0.7692	Intermediate Similarity	NPD7507	Approved
0.7642	Intermediate Similarity	NPD6650	Approved
0.7642	Intermediate Similarity	NPD6649	Approved
0.7623	Intermediate Similarity	NPD6372	Approved
0.7623	Intermediate Similarity	NPD6373	Approved
0.7619	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6033	Approved
0.7561	Intermediate Similarity	NPD4634	Approved
0.7541	Intermediate Similarity	NPD6881	Approved
0.7541	Intermediate Similarity	NPD6899	Approved
0.7521	Intermediate Similarity	NPD6402	Approved
0.7521	Intermediate Similarity	NPD5739	Approved
0.7521	Intermediate Similarity	NPD7128	Approved
0.7521	Intermediate Similarity	NPD6675	Approved
0.752	Intermediate Similarity	NPD4632	Approved
0.7519	Intermediate Similarity	NPD7503	Approved
0.75	Intermediate Similarity	NPD8130	Phase 1
0.7459	Intermediate Similarity	NPD5697	Approved
0.7419	Intermediate Similarity	NPD7102	Approved
0.7419	Intermediate Similarity	NPD7290	Approved
0.7419	Intermediate Similarity	NPD6883	Approved
0.7398	Intermediate Similarity	NPD6686	Approved
0.7398	Intermediate Similarity	NPD7320	Approved
0.7373	Intermediate Similarity	NPD6084	Phase 2
0.7373	Intermediate Similarity	NPD6083	Phase 2
0.736	Intermediate Similarity	NPD6869	Approved
0.736	Intermediate Similarity	NPD6617	Approved
0.736	Intermediate Similarity	NPD6847	Approved
0.735	Intermediate Similarity	NPD5695	Phase 3
0.7339	Intermediate Similarity	NPD6014	Approved
0.7339	Intermediate Similarity	NPD6013	Approved
0.7339	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6012	Approved
0.7333	Intermediate Similarity	NPD5956	Approved
0.7317	Intermediate Similarity	NPD5701	Approved
0.7273	Intermediate Similarity	NPD7604	Phase 2
0.7258	Intermediate Similarity	NPD6011	Approved
0.7252	Intermediate Similarity	NPD5983	Phase 2
0.725	Intermediate Similarity	NPD5285	Approved
0.725	Intermediate Similarity	NPD5286	Approved
0.725	Intermediate Similarity	NPD4696	Approved
0.7227	Intermediate Similarity	NPD4755	Approved
0.7176	Intermediate Similarity	NPD8377	Approved
0.7176	Intermediate Similarity	NPD8294	Approved
0.7167	Intermediate Similarity	NPD5696	Approved
0.7165	Intermediate Similarity	NPD6053	Discontinued
0.7164	Intermediate Similarity	NPD6336	Discontinued
0.7154	Intermediate Similarity	NPD7328	Approved
0.7154	Intermediate Similarity	NPD7327	Approved
0.7131	Intermediate Similarity	NPD5211	Phase 2
0.7131	Intermediate Similarity	NPD5224	Approved
0.7131	Intermediate Similarity	NPD5226	Approved
0.7131	Intermediate Similarity	NPD4633	Approved
0.7131	Intermediate Similarity	NPD5225	Approved
0.7121	Intermediate Similarity	NPD8379	Approved
0.7121	Intermediate Similarity	NPD8033	Approved
0.7121	Intermediate Similarity	NPD8296	Approved
0.7121	Intermediate Similarity	NPD8378	Approved
0.7121	Intermediate Similarity	NPD8380	Approved
0.7121	Intermediate Similarity	NPD8335	Approved
0.7109	Intermediate Similarity	NPD8133	Approved
0.7107	Intermediate Similarity	NPD4700	Approved
0.7099	Intermediate Similarity	NPD7516	Approved
0.7087	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5174	Approved
0.7073	Intermediate Similarity	NPD5175	Approved
0.7069	Intermediate Similarity	NPD4753	Phase 2
0.7059	Intermediate Similarity	NPD4629	Approved
0.7059	Intermediate Similarity	NPD5210	Approved
0.7049	Intermediate Similarity	NPD5223	Approved
0.7016	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5141	Approved
0.7	Intermediate Similarity	NPD6274	Approved
0.6984	Remote Similarity	NPD4730	Approved
0.6984	Remote Similarity	NPD4729	Approved
0.697	Remote Similarity	NPD7100	Approved
0.697	Remote Similarity	NPD7101	Approved
0.696	Remote Similarity	NPD4768	Approved
0.696	Remote Similarity	NPD4767	Approved
0.6947	Remote Similarity	NPD7115	Discovery
0.6905	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6335	Approved
0.6889	Remote Similarity	NPD6067	Discontinued
0.6875	Remote Similarity	NPD5247	Approved
0.6875	Remote Similarity	NPD5250	Approved
0.6875	Remote Similarity	NPD5249	Phase 3
0.6875	Remote Similarity	NPD5251	Approved
0.6875	Remote Similarity	NPD5248	Approved
0.6866	Remote Similarity	NPD8513	Phase 3
0.6866	Remote Similarity	NPD8517	Approved
0.6866	Remote Similarity	NPD8516	Approved
0.6866	Remote Similarity	NPD8515	Approved
0.685	Remote Similarity	NPD5128	Approved
0.6842	Remote Similarity	NPD4522	Approved
0.6833	Remote Similarity	NPD5282	Discontinued
0.6825	Remote Similarity	NPD6008	Approved
0.6818	Remote Similarity	NPD6317	Approved
0.6815	Remote Similarity	NPD8080	Discontinued
0.6812	Remote Similarity	NPD8337	Approved
0.6812	Remote Similarity	NPD8336	Approved
0.681	Remote Similarity	NPD5690	Phase 2
0.6807	Remote Similarity	NPD6050	Approved
0.68	Remote Similarity	NPD4754	Approved
0.678	Remote Similarity	NPD6673	Approved
0.678	Remote Similarity	NPD6080	Approved
0.678	Remote Similarity	NPD6904	Approved
0.6767	Remote Similarity	NPD6313	Approved
0.6767	Remote Similarity	NPD6314	Approved
0.6744	Remote Similarity	NPD6371	Approved
0.6741	Remote Similarity	NPD6908	Approved
0.6741	Remote Similarity	NPD6909	Approved
0.6724	Remote Similarity	NPD5329	Approved
0.6723	Remote Similarity	NPD5692	Phase 3
0.6721	Remote Similarity	NPD5221	Approved
0.6721	Remote Similarity	NPD5222	Approved
0.6721	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD4697	Phase 3
0.6719	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5737	Approved
0.6695	Remote Similarity	NPD6672	Approved
0.6692	Remote Similarity	NPD5216	Approved
0.6692	Remote Similarity	NPD5217	Approved
0.6692	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD6079	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6639	Remote Similarity	NPD5328	Approved
0.6638	Remote Similarity	NPD4197	Approved
0.6638	Remote Similarity	NPD3666	Approved
0.6638	Remote Similarity	NPD3133	Approved
0.6638	Remote Similarity	NPD3665	Phase 1
0.6618	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5135	Approved
0.6615	Remote Similarity	NPD5169	Approved
0.6612	Remote Similarity	NPD4202	Approved
0.6612	Remote Similarity	NPD6399	Phase 3
0.6565	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD5127	Approved
0.6555	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5693	Phase 1
0.6525	Remote Similarity	NPD6684	Approved
0.6525	Remote Similarity	NPD5330	Approved
0.6525	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6098	Approved
0.6525	Remote Similarity	NPD7334	Approved
0.6525	Remote Similarity	NPD7146	Approved
0.6525	Remote Similarity	NPD6409	Approved
0.6525	Remote Similarity	NPD7521	Approved
0.6493	Remote Similarity	NPD6868	Approved
0.6485	Remote Similarity	NPD7799	Discontinued
0.6466	Remote Similarity	NPD4223	Phase 3
0.6466	Remote Similarity	NPD4221	Approved
0.6438	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD5167	Approved
0.6417	Remote Similarity	NPD6903	Approved
0.641	Remote Similarity	NPD4788	Approved
0.64	Remote Similarity	NPD7902	Approved
0.6395	Remote Similarity	NPD6333	Approved
0.6395	Remote Similarity	NPD6334	Approved
0.6393	Remote Similarity	NPD6411	Approved
0.6389	Remote Similarity	NPD8338	Approved
0.6389	Remote Similarity	NPD6845	Suspended
0.6387	Remote Similarity	NPD3618	Phase 1
0.6371	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD5654	Approved
0.6364	Remote Similarity	NPD6914	Discontinued
0.6357	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD4786	Approved
0.6349	Remote Similarity	NPD7638	Approved
0.6324	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5207	Approved
0.6299	Remote Similarity	NPD7639	Approved
0.6299	Remote Similarity	NPD7640	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