NPASS Compound

Structure

CID160413 OpenBabel06191715532D 44 50 0 0 1 0 0 0 0 0999 V2000 -1.9406 -2.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7400 -0.9834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1269 -1.6931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5297 -0.7367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2037 0.5676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6938 1.4165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5508 3.8672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0410 4.7161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2290 1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1668 1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2290 3.8672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8646 2.8869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0157 -0.5440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8646 -0.0539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6822 2.3968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3800 4.3573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7136 2.3968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2290 2.8869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0157 2.3968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6822 1.4165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2290 0.9264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6869 -1.2372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5522 -0.8099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1668 -0.0539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8646 0.9264 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5311 2.8869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3800 1.4165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2290 -0.0539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1668 0.9264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6822 -0.5440 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6822 1.4165 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5311 -0.0539 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.8725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7136 1.4165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5311 3.8672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3800 2.3968 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0157 1.4165 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5311 0.9264 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3800 -0.5440 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 -4.0779 -0.5440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7664 1.7232 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2857 -0.9191 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9775 0.0733 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 34 1 0 0 0 0 6 34 1 0 0 0 0 7 35 1 0 0 0 0 8 35 1 0 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 12 17 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 20 1 0 0 0 0 15 26 1 0 0 0 0 16 35 1 0 0 0 0 17 34 1 0 0 0 0 18 36 1 0 0 0 0 19 37 1 0 0 0 0 21 27 2 0 0 0 0 21 28 1 0 0 0 0 22 39 1 0 0 0 0 23 40 1 0 0 0 0 24 29 2 0 0 0 0 24 30 1 0 0 0 0 25 34 1 0 0 0 0 25 37 1 6 0 0 0 26 35 1 0 0 0 0 26 36 1 6 0 0 0 27 36 1 0 0 0 0 27 38 1 0 0 0 0 28 39 1 0 0 0 0 28 41 2 0 0 0 0 29 31 1 0 0 0 0 29 37 1 0 0 0 0 30 32 1 0 0 0 0 30 40 1 6 0 0 0 31 33 1 0 0 0 0 31 38 1 1 0 0 0 32 38 1 1 0 0 0 32 39 1 0 0 0 0 33 40 1 0 0 0 0 33 42 2 0 0 0 0 36 9 1 6 0 0 0 37 10 1 6 0 0 0 38 20 1 6 0 0 0 39 43 1 1 0 0 0 40 44 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	604.45
Volume:	665.116
LogP:	8.077
LogD:	5.618
LogS:	-6.331
# Rotatable Bonds:	2
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.333
Synthetic Accessibility Score:	6.821
Fsp3:	0.85
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-5.095
MDCK Permeability:	1.2864365089626517e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.804
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.654
Plasma Protein Binding (PPB):	94.62371826171875%
Volume Distribution (VD):	1.514
Pgp-substrate:	3.091535806655884%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.176
CYP2C19-substrate:	0.935
CYP2C9-inhibitor:	0.199
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.024
CYP3A4-inhibitor:	0.847
CYP3A4-substrate:	0.923

ADMET: Excretion

Clearance (CL):	5.662
Half-life (T1/2):	0.002

ADMET: Toxicity

hERG Blockers:	0.97
Human Hepatotoxicity (H-HT):	0.421
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.491
Maximum Recommended Daily Dose:	0.743
Skin Sensitization:	0.118
Carcinogencity:	0.458
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC160413

Natural Product ID:	NPC160413
*Common Name:**	Maytenone
IUPAC Name:	n.a.
Synonyms:	Maytenone
Standard InCHIKey:	XIBQGXZPEAWMMS-JKOYJTFMSA-N
Standard InCHI:	InChI=1S/C40H60O4/c1-22(2)39(43)28(41)21-27-36(9)18-11-16-35(7,8)26(36)15-20-38(27)31-29-24(30(32(38)39)40(44,23(3)4)33(31)42)13-14-25-34(5,6)17-12-19-37(25,29)10/h21-23,25-26,30-32,43-44H,11-20H2,1-10H3/t25-,26-,30-,31-,32+,36-,37-,38-,39-,40+/m0/s1
SMILES:	CC(C)[C@@]1(C(=O)C=C2[C@@]3(C)CCCC(C)(C)[C@@H]3CC[C@]32[C@H]2C4=C(CC[C@H]5C(C)(C)CCC[C@]45C)[C@@H]([C@@H]13)[C@](C(C)C)(C2=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503196
PubChem CID:	44558957
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO27625	Buddleja globosa	Species	Scrophulariaceae	Eukaryota	Roots	London	n.a.	PMID[10514305]
NPO27625	Buddleja globosa	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000021]
NPO5565	Harpagophytum procumbens	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27625	Buddleja globosa	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5565	Harpagophytum procumbens	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27625	Buddleja globosa	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5565	Harpagophytum procumbens	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
MIC	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT328	Organism	Epidermophyton floccosum	Epidermophyton floccosum	MIC	=	625000.0	nM	PMID[480191]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	625000.0	nM	PMID[480191]
NPT4353	Organism	Trichophyton interdigitale	Trichophyton interdigitale	MIC	=	625000.0	nM	PMID[480191]

☑ 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 NPC160413 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	252
0.1-0.2	1833
0.2-0.3	6629
0.3-0.4	14649
0.4-0.5	9132
0.5-0.6	5681
0.6-0.7	3696
0.7-0.8	766
0.8-0.85	55
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC65615
0.8889	High Similarity	NPC68148
0.8617	High Similarity	NPC147232
0.8571	High Similarity	NPC230387
0.8511	High Similarity	NPC23170
0.8511	High Similarity	NPC474328
0.8444	Intermediate Similarity	NPC469993
0.8427	Intermediate Similarity	NPC53733
0.8421	Intermediate Similarity	NPC139570
0.8404	Intermediate Similarity	NPC211230
0.8333	Intermediate Similarity	NPC157113
0.8333	Intermediate Similarity	NPC62516
0.8295	Intermediate Similarity	NPC18955
0.828	Intermediate Similarity	NPC112454
0.8202	Intermediate Similarity	NPC473217
0.82	Intermediate Similarity	NPC179208
0.8132	Intermediate Similarity	NPC96095
0.8132	Intermediate Similarity	NPC251170
0.8125	Intermediate Similarity	NPC74751
0.8119	Intermediate Similarity	NPC213366
0.8119	Intermediate Similarity	NPC284865
0.8105	Intermediate Similarity	NPC474525
0.8105	Intermediate Similarity	NPC145067
0.8105	Intermediate Similarity	NPC470036
0.8105	Intermediate Similarity	NPC233455
0.8105	Intermediate Similarity	NPC174167
0.8105	Intermediate Similarity	NPC99380
0.8105	Intermediate Similarity	NPC65120
0.8105	Intermediate Similarity	NPC158030
0.8105	Intermediate Similarity	NPC4036
0.8085	Intermediate Similarity	NPC69627
0.8068	Intermediate Similarity	NPC476808
0.8065	Intermediate Similarity	NPC73064
0.8061	Intermediate Similarity	NPC473456
0.8043	Intermediate Similarity	NPC133954
0.8041	Intermediate Similarity	NPC473240
0.8021	Intermediate Similarity	NPC214756
0.8021	Intermediate Similarity	NPC158059
0.8021	Intermediate Similarity	NPC295643
0.8021	Intermediate Similarity	NPC202728
0.8021	Intermediate Similarity	NPC118519
0.8021	Intermediate Similarity	NPC272075
0.8021	Intermediate Similarity	NPC263780
0.8	Intermediate Similarity	NPC118964
0.8	Intermediate Similarity	NPC475863
0.8	Intermediate Similarity	NPC55869
0.8	Intermediate Similarity	NPC46441
0.8	Intermediate Similarity	NPC470034
0.798	Intermediate Similarity	NPC260149
0.798	Intermediate Similarity	NPC58942
0.7959	Intermediate Similarity	NPC327179
0.7959	Intermediate Similarity	NPC476318
0.7959	Intermediate Similarity	NPC476327
0.7959	Intermediate Similarity	NPC473158
0.7957	Intermediate Similarity	NPC213412
0.7957	Intermediate Similarity	NPC74363
0.7957	Intermediate Similarity	NPC475862
0.7938	Intermediate Similarity	NPC114159
0.7938	Intermediate Similarity	NPC191412
0.7938	Intermediate Similarity	NPC474529
0.7938	Intermediate Similarity	NPC212812
0.7938	Intermediate Similarity	NPC6818
0.7938	Intermediate Similarity	NPC293086
0.7938	Intermediate Similarity	NPC474882
0.7938	Intermediate Similarity	NPC148964
0.7935	Intermediate Similarity	NPC180834
0.7917	Intermediate Similarity	NPC168027
0.7917	Intermediate Similarity	NPC38754
0.7917	Intermediate Similarity	NPC185936
0.7917	Intermediate Similarity	NPC187722
0.7917	Intermediate Similarity	NPC470590
0.7917	Intermediate Similarity	NPC60755
0.7917	Intermediate Similarity	NPC77099
0.7917	Intermediate Similarity	NPC285184
0.7917	Intermediate Similarity	NPC105189
0.7917	Intermediate Similarity	NPC235704
0.7917	Intermediate Similarity	NPC248913
0.7912	Intermediate Similarity	NPC69101
0.7912	Intermediate Similarity	NPC251779
0.7912	Intermediate Similarity	NPC310989
0.79	Intermediate Similarity	NPC15390
0.7895	Intermediate Similarity	NPC30522
0.7895	Intermediate Similarity	NPC64872
0.7895	Intermediate Similarity	NPC274330
0.7895	Intermediate Similarity	NPC198664
0.7895	Intermediate Similarity	NPC25906
0.7895	Intermediate Similarity	NPC290972
0.7895	Intermediate Similarity	NPC143232
0.7889	Intermediate Similarity	NPC287063
0.7889	Intermediate Similarity	NPC476809
0.7889	Intermediate Similarity	NPC108955
0.7889	Intermediate Similarity	NPC469637
0.7879	Intermediate Similarity	NPC26413
0.7879	Intermediate Similarity	NPC189880
0.7879	Intermediate Similarity	NPC18509
0.7872	Intermediate Similarity	NPC471792
0.7865	Intermediate Similarity	NPC30321
0.7857	Intermediate Similarity	NPC148523
0.7857	Intermediate Similarity	NPC474602
0.7857	Intermediate Similarity	NPC473170
0.7857	Intermediate Similarity	NPC777
0.7849	Intermediate Similarity	NPC474537
0.7841	Intermediate Similarity	NPC92080
0.7835	Intermediate Similarity	NPC477436
0.7835	Intermediate Similarity	NPC118490
0.7835	Intermediate Similarity	NPC477435
0.7835	Intermediate Similarity	NPC229281
0.7826	Intermediate Similarity	NPC105803
0.7812	Intermediate Similarity	NPC120968
0.7812	Intermediate Similarity	NPC18872
0.7812	Intermediate Similarity	NPC7260
0.7812	Intermediate Similarity	NPC273621
0.7812	Intermediate Similarity	NPC111110
0.7812	Intermediate Similarity	NPC126369
0.7812	Intermediate Similarity	NPC227467
0.7812	Intermediate Similarity	NPC210037
0.7812	Intermediate Similarity	NPC475823
0.7812	Intermediate Similarity	NPC470589
0.7812	Intermediate Similarity	NPC223093
0.7812	Intermediate Similarity	NPC477872
0.7812	Intermediate Similarity	NPC474728
0.7812	Intermediate Similarity	NPC193750
0.7812	Intermediate Similarity	NPC120840
0.7812	Intermediate Similarity	NPC474209
0.7812	Intermediate Similarity	NPC290614
0.7812	Intermediate Similarity	NPC291028
0.7812	Intermediate Similarity	NPC130278
0.7812	Intermediate Similarity	NPC113989
0.7802	Intermediate Similarity	NPC162632
0.7802	Intermediate Similarity	NPC274050
0.7802	Intermediate Similarity	NPC471898
0.7802	Intermediate Similarity	NPC267691
0.7802	Intermediate Similarity	NPC3915
0.7802	Intermediate Similarity	NPC263272
0.78	Intermediate Similarity	NPC471966
0.7789	Intermediate Similarity	NPC472802
0.7789	Intermediate Similarity	NPC52169
0.7789	Intermediate Similarity	NPC470629
0.7789	Intermediate Similarity	NPC290690
0.7789	Intermediate Similarity	NPC206060
0.7789	Intermediate Similarity	NPC182797
0.7789	Intermediate Similarity	NPC473242
0.7789	Intermediate Similarity	NPC17733
0.7789	Intermediate Similarity	NPC474512
0.7789	Intermediate Similarity	NPC474925
0.7789	Intermediate Similarity	NPC470524
0.7789	Intermediate Similarity	NPC181225
0.7778	Intermediate Similarity	NPC207922
0.7778	Intermediate Similarity	NPC259733
0.7778	Intermediate Similarity	NPC469545
0.7778	Intermediate Similarity	NPC96859
0.7778	Intermediate Similarity	NPC116457
0.7778	Intermediate Similarity	NPC98874
0.7778	Intermediate Similarity	NPC132824
0.7778	Intermediate Similarity	NPC61369
0.7778	Intermediate Similarity	NPC5532
0.7778	Intermediate Similarity	NPC328162
0.7778	Intermediate Similarity	NPC158371
0.7778	Intermediate Similarity	NPC305483
0.7766	Intermediate Similarity	NPC95594
0.7766	Intermediate Similarity	NPC56588
0.7766	Intermediate Similarity	NPC477579
0.7766	Intermediate Similarity	NPC158393
0.7766	Intermediate Similarity	NPC72638
0.7766	Intermediate Similarity	NPC235341
0.7755	Intermediate Similarity	NPC472976
0.7755	Intermediate Similarity	NPC245972
0.7755	Intermediate Similarity	NPC196485
0.7755	Intermediate Similarity	NPC477439
0.7755	Intermediate Similarity	NPC472977
0.7755	Intermediate Similarity	NPC471207
0.7732	Intermediate Similarity	NPC472978
0.7723	Intermediate Similarity	NPC144956
0.7717	Intermediate Similarity	NPC163236
0.7717	Intermediate Similarity	NPC48362
0.7708	Intermediate Similarity	NPC61543
0.7708	Intermediate Similarity	NPC130520
0.7708	Intermediate Similarity	NPC263393
0.7708	Intermediate Similarity	NPC474245
0.7708	Intermediate Similarity	NPC275740
0.7708	Intermediate Similarity	NPC234346
0.7708	Intermediate Similarity	NPC121798
0.7708	Intermediate Similarity	NPC127689
0.7708	Intermediate Similarity	NPC225585
0.7708	Intermediate Similarity	NPC59263
0.7708	Intermediate Similarity	NPC293048
0.7708	Intermediate Similarity	NPC470588
0.7708	Intermediate Similarity	NPC86319
0.7708	Intermediate Similarity	NPC472973
0.7708	Intermediate Similarity	NPC270768
0.77	Intermediate Similarity	NPC9613
0.77	Intermediate Similarity	NPC190554
0.77	Intermediate Similarity	NPC259788
0.77	Intermediate Similarity	NPC247139
0.77	Intermediate Similarity	NPC255589
0.77	Intermediate Similarity	NPC187933
0.7692	Intermediate Similarity	NPC2482
0.7692	Intermediate Similarity	NPC37038
0.7684	Intermediate Similarity	NPC242468
0.7684	Intermediate Similarity	NPC68160

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 NPC160413 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	2132
0.2-0.3	4148
0.3-0.4	1829
0.4-0.5	451
0.5-0.6	147
0.6-0.7	152
0.7-0.8	37
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.828	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7748	Approved
0.8105	Intermediate Similarity	NPD7515	Phase 2
0.8061	Intermediate Similarity	NPD7902	Approved
0.7889	Intermediate Similarity	NPD4695	Discontinued
0.7879	Intermediate Similarity	NPD4755	Approved
0.7755	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7900	Approved
0.7723	Intermediate Similarity	NPD5286	Approved
0.7723	Intermediate Similarity	NPD4696	Approved
0.7723	Intermediate Similarity	NPD5285	Approved
0.7723	Intermediate Similarity	NPD4700	Approved
0.7708	Intermediate Similarity	NPD5328	Approved
0.766	Intermediate Similarity	NPD5329	Approved
0.7647	Intermediate Similarity	NPD5223	Approved
0.76	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5222	Approved
0.76	Intermediate Similarity	NPD5221	Approved
0.76	Intermediate Similarity	NPD4697	Phase 3
0.7579	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD5211	Phase 2
0.7573	Intermediate Similarity	NPD5225	Approved
0.7573	Intermediate Similarity	NPD5224	Approved
0.7573	Intermediate Similarity	NPD5226	Approved
0.7573	Intermediate Similarity	NPD4633	Approved
0.7553	Intermediate Similarity	NPD4197	Approved
0.7551	Intermediate Similarity	NPD6079	Approved
0.7525	Intermediate Similarity	NPD5173	Approved
0.7524	Intermediate Similarity	NPD6402	Approved
0.7524	Intermediate Similarity	NPD5739	Approved
0.7524	Intermediate Similarity	NPD6675	Approved
0.7524	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD5175	Approved
0.75	Intermediate Similarity	NPD3573	Approved
0.75	Intermediate Similarity	NPD4754	Approved
0.75	Intermediate Similarity	NPD5174	Approved
0.7473	Intermediate Similarity	NPD3617	Approved
0.7429	Intermediate Similarity	NPD5141	Approved
0.7426	Intermediate Similarity	NPD7614	Phase 1
0.7396	Intermediate Similarity	NPD4694	Approved
0.7396	Intermediate Similarity	NPD3618	Phase 1
0.7396	Intermediate Similarity	NPD5690	Phase 2
0.7396	Intermediate Similarity	NPD5280	Approved
0.7383	Intermediate Similarity	NPD6881	Approved
0.7383	Intermediate Similarity	NPD7320	Approved
0.7383	Intermediate Similarity	NPD6899	Approved
0.7358	Intermediate Similarity	NPD4768	Approved
0.7358	Intermediate Similarity	NPD4767	Approved
0.7347	Intermediate Similarity	NPD4753	Phase 2
0.734	Intermediate Similarity	NPD4223	Phase 3
0.734	Intermediate Similarity	NPD4221	Approved
0.7339	Intermediate Similarity	NPD8130	Phase 1
0.7315	Intermediate Similarity	NPD6373	Approved
0.7315	Intermediate Similarity	NPD6372	Approved
0.73	Intermediate Similarity	NPD4202	Approved
0.729	Intermediate Similarity	NPD5697	Approved
0.729	Intermediate Similarity	NPD5701	Approved
0.7273	Intermediate Similarity	NPD8297	Approved
0.7248	Intermediate Similarity	NPD6883	Approved
0.7248	Intermediate Similarity	NPD7290	Approved
0.7248	Intermediate Similarity	NPD7102	Approved
0.7222	Intermediate Similarity	NPD5128	Approved
0.7222	Intermediate Similarity	NPD6011	Approved
0.7222	Intermediate Similarity	NPD4730	Approved
0.7222	Intermediate Similarity	NPD4729	Approved
0.7188	Intermediate Similarity	NPD4786	Approved
0.7182	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6649	Approved
0.7182	Intermediate Similarity	NPD6847	Approved
0.7182	Intermediate Similarity	NPD6869	Approved
0.7182	Intermediate Similarity	NPD6617	Approved
0.7182	Intermediate Similarity	NPD6650	Approved
0.7158	Intermediate Similarity	NPD3667	Approved
0.7156	Intermediate Similarity	NPD6012	Approved
0.7156	Intermediate Similarity	NPD6013	Approved
0.7156	Intermediate Similarity	NPD6014	Approved
0.7117	Intermediate Similarity	NPD6882	Approved
0.7094	Intermediate Similarity	NPD8328	Phase 3
0.7091	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4634	Approved
0.7091	Intermediate Similarity	NPD5249	Phase 3
0.7091	Intermediate Similarity	NPD5135	Approved
0.7091	Intermediate Similarity	NPD5169	Approved
0.7091	Intermediate Similarity	NPD5247	Approved
0.7091	Intermediate Similarity	NPD5248	Approved
0.7091	Intermediate Similarity	NPD5251	Approved
0.7091	Intermediate Similarity	NPD5250	Approved
0.7087	Intermediate Similarity	NPD7732	Phase 3
0.7041	Intermediate Similarity	NPD5205	Approved
0.7041	Intermediate Similarity	NPD4690	Approved
0.7041	Intermediate Similarity	NPD4689	Approved
0.7041	Intermediate Similarity	NPD4623	Approved
0.7041	Intermediate Similarity	NPD4688	Approved
0.7041	Intermediate Similarity	NPD4138	Approved
0.7041	Intermediate Similarity	NPD4519	Discontinued
0.7041	Intermediate Similarity	NPD4693	Phase 3
0.7041	Intermediate Similarity	NPD5279	Phase 3
0.703	Intermediate Similarity	NPD5284	Approved
0.703	Intermediate Similarity	NPD5281	Approved
0.7027	Intermediate Similarity	NPD5217	Approved
0.7027	Intermediate Similarity	NPD5216	Approved
0.7027	Intermediate Similarity	NPD5127	Approved
0.7027	Intermediate Similarity	NPD5215	Approved
0.7021	Intermediate Similarity	NPD7645	Phase 2
0.7019	Intermediate Similarity	NPD6083	Phase 2
0.7019	Intermediate Similarity	NPD6084	Phase 2
0.701	Intermediate Similarity	NPD3666	Approved
0.701	Intermediate Similarity	NPD3665	Phase 1
0.701	Intermediate Similarity	NPD3133	Approved
0.7	Intermediate Similarity	NPD6080	Approved
0.7	Intermediate Similarity	NPD6673	Approved
0.7	Intermediate Similarity	NPD6904	Approved
0.699	Remote Similarity	NPD4629	Approved
0.699	Remote Similarity	NPD5210	Approved
0.699	Remote Similarity	NPD5695	Phase 3
0.6961	Remote Similarity	NPD5133	Approved
0.6961	Remote Similarity	NPD6399	Phase 3
0.6947	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5168	Approved
0.6903	Remote Similarity	NPD4632	Approved
0.69	Remote Similarity	NPD5737	Approved
0.69	Remote Similarity	NPD6672	Approved
0.6897	Remote Similarity	NPD7341	Phase 2
0.6875	Remote Similarity	NPD8028	Phase 2
0.687	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD8035	Phase 2
0.6863	Remote Similarity	NPD8034	Phase 2
0.6863	Remote Similarity	NPD6050	Approved
0.6842	Remote Similarity	NPD5167	Approved
0.6837	Remote Similarity	NPD3668	Phase 3
0.6818	Remote Similarity	NPD7331	Phase 2
0.681	Remote Similarity	NPD6335	Approved
0.6792	Remote Similarity	NPD5696	Approved
0.6783	Remote Similarity	NPD6274	Approved
0.6771	Remote Similarity	NPD7525	Registered
0.6768	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5692	Phase 3
0.6752	Remote Similarity	NPD7100	Approved
0.6752	Remote Similarity	NPD7101	Approved
0.6733	Remote Similarity	NPD4518	Approved
0.6733	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6008	Approved
0.6724	Remote Similarity	NPD6317	Approved
0.6724	Remote Similarity	NPD6009	Approved
0.6721	Remote Similarity	NPD7736	Approved
0.6701	Remote Similarity	NPD4139	Approved
0.6701	Remote Similarity	NPD4692	Approved
0.67	Remote Similarity	NPD6098	Approved
0.6699	Remote Similarity	NPD5694	Approved
0.6699	Remote Similarity	NPD5693	Phase 1
0.6695	Remote Similarity	NPD6059	Approved
0.6695	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD4195	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6313	Approved
0.6639	Remote Similarity	NPD6909	Approved
0.6639	Remote Similarity	NPD6908	Approved
0.6638	Remote Similarity	NPD6868	Approved
0.6606	Remote Similarity	NPD5091	Approved
0.6602	Remote Similarity	NPD4096	Approved
0.66	Remote Similarity	NPD1696	Phase 3
0.6593	Remote Similarity	NPD4137	Phase 3
0.6583	Remote Similarity	NPD6370	Approved
0.6566	Remote Similarity	NPD4788	Approved
0.6555	Remote Similarity	NPD6319	Approved
0.6549	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6411	Approved
0.6535	Remote Similarity	NPD7521	Approved
0.6535	Remote Similarity	NPD5330	Approved
0.6535	Remote Similarity	NPD7334	Approved
0.6535	Remote Similarity	NPD6409	Approved
0.6535	Remote Similarity	NPD6684	Approved
0.6535	Remote Similarity	NPD7146	Approved
0.6529	Remote Similarity	NPD7604	Phase 2
0.6522	Remote Similarity	NPD4747	Approved
0.6522	Remote Similarity	NPD4691	Approved
0.6509	Remote Similarity	NPD5654	Approved
0.6504	Remote Similarity	NPD8293	Discontinued
0.65	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5983	Phase 2
0.65	Remote Similarity	NPD6016	Approved
0.65	Remote Similarity	NPD6015	Approved
0.6489	Remote Similarity	NPD5733	Approved
0.6484	Remote Similarity	NPD5360	Phase 3
0.6484	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7638	Approved
0.6475	Remote Similarity	NPD7492	Approved
0.6446	Remote Similarity	NPD5988	Approved
0.6441	Remote Similarity	NPD7115	Discovery
0.6423	Remote Similarity	NPD6616	Approved
0.6423	Remote Similarity	NPD6336	Discontinued
0.6422	Remote Similarity	NPD7640	Approved
0.6422	Remote Similarity	NPD7639	Approved
0.6415	Remote Similarity	NPD6001	Approved
0.6408	Remote Similarity	NPD5208	Approved
0.6408	Remote Similarity	NPD6903	Approved
0.6389	Remote Similarity	NPD5959	Approved
0.6372	Remote Similarity	NPD6412	Phase 2
0.6371	Remote Similarity	NPD7078	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