NPASS Compound

Structure

NPC475460 OpenBabel07101718292D 63 66 0 0 1 0 0 0 0 0999 V2000 4.1923 -8.4586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7844 -3.4465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3455 -2.3051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3159 -8.9665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3707 0.3949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0130 -7.7421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4826 -5.2282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7734 2.1035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1804 -3.5761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4536 -9.6087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9086 0.8514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4312 -7.0523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8339 -4.5101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0276 -1.7592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9325 -8.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6096 -1.0114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6834 -0.4150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5664 -7.0947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5749 -5.3712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4722 0.7012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9353 -6.1615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6987 -7.0233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2577 1.8281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6834 -7.6487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8339 -3.5536 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4426 -2.6210 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -8.0637 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8618 -0.4150 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0276 -6.3044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6210 -5.4426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8216 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4312 -1.0114 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5203 -7.0233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1137 -6.1615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1903 1.6152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3965 -5.3712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7448 -7.0947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6071 1.1269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8891 -8.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2060 -1.7592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4426 -5.4426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2060 -6.3044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8891 0.2128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6555 -4.5101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6096 -7.0523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9325 0.2128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1076 -0.3350 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9962 -9.2270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0159 -1.2503 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6060 -4.6172 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2860 -7.7286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8254 1.1634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0591 -7.8136 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0676 -6.0900 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8409 2.3164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2265 -3.6476 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9148 -8.8183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2580 1.5526 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8216 -8.0637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6210 -2.6210 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6555 -3.5536 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8618 -7.6487 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 6 53 1 0 0 0 0 7 54 1 0 0 0 0 8 55 1 0 0 0 0 9 56 1 0 0 0 0 10 57 1 0 0 0 0 11 58 1 0 0 0 0 12 24 1 0 0 0 0 12 29 1 0 0 0 0 13 25 1 0 0 0 0 13 30 1 0 0 0 0 14 26 1 0 0 0 0 14 32 1 0 0 0 0 15 27 1 0 0 0 0 15 39 1 0 0 0 0 16 28 1 0 0 0 0 16 40 1 0 0 0 0 17 31 1 0 0 0 0 17 32 1 0 0 0 0 18 29 2 0 0 0 0 18 33 1 0 0 0 0 19 30 2 0 0 0 0 19 34 1 0 0 0 0 20 31 2 0 0 0 0 20 35 1 0 0 0 0 21 33 2 0 0 0 0 21 36 1 0 0 0 0 22 34 2 0 0 0 0 22 37 1 0 0 0 0 23 35 2 0 0 0 0 23 38 1 0 0 0 0 24 1 1 1 0 0 0 24 59 1 0 0 0 0 25 2 1 1 0 0 0 25 60 1 0 0 0 0 26 3 1 1 0 0 0 26 61 1 0 0 0 0 27 4 1 1 0 0 0 27 62 1 0 0 0 0 28 5 1 1 0 0 0 28 63 1 0 0 0 0 29 41 1 0 0 0 0 30 42 1 0 0 0 0 31 43 1 0 0 0 0 32 47 1 6 0 0 0 33 53 1 0 0 0 0 34 54 1 0 0 0 0 35 55 1 0 0 0 0 36 41 2 0 0 0 0 36 56 1 0 0 0 0 37 42 2 0 0 0 0 37 57 1 0 0 0 0 38 43 2 0 0 0 0 38 58 1 0 0 0 0 39 48 2 0 0 0 0 39 59 1 0 0 0 0 40 49 2 0 0 0 0 40 60 1 0 0 0 0 41 44 1 0 0 0 0 42 45 1 0 0 0 0 43 46 1 0 0 0 0 44 50 2 0 0 0 0 44 61 1 0 0 0 0 45 51 2 0 0 0 0 45 62 1 0 0 0 0 46 52 2 0 0 0 0 46 63 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	882.37
Volume:	882.469
LogP:	5.714
LogD:	3.452
LogS:	-7.244
# Rotatable Bonds:	6
TPSA:	207.11
# H-Bond Aceptor:	17
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.229
Synthetic Accessibility Score:	5.284
Fsp3:	0.5
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:	-4.827
MDCK Permeability:	8.064325811574236e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.127

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	52.96318435668945%
Volume Distribution (VD):	0.522
Pgp-substrate:	69.51509094238281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.226
CYP1A2-substrate:	0.36
CYP2C19-inhibitor:	0.806
CYP2C19-substrate:	0.176
CYP2C9-inhibitor:	0.971
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	0.889
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	9.469
Half-life (T1/2):	0.075

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.752
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.931
Carcinogencity:	0.467
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.016

Download Data

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

Natural Product: NPC475460

Natural Product ID:	NPC475460
*Common Name:**	KMRNOVUURVKRST-YETHLXGISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KMRNOVUURVKRST-YETHLXGISA-N
Standard InCHI:	InChI=1S/C46H58O17/c1-24-12-29-18-33(53-6)21-36(56-9)41(29)44(50)61-26(3)14-32(47)17-31-20-35(55-8)23-38(58-11)43(31)46(52)63-28(5)16-40(49)60-25(2)13-30-19-34(54-7)22-37(57-10)42(30)45(51)62-27(4)15-39(48)59-24/h18-28,32,47H,12-17H2,1-11H3/t24-,25-,26-,27-,28-,32-/m1/s1
SMILES:	CC1CC(CC2=C(C(=CC(=C2)OC)OC)C(=O)OC(CC(=O)OC(CC3=C(C(=CC(=C3)OC)OC)C(=O)OC(CC(=O)OC(CC4=C(C(=CC(=C4)OC)OC)C(=O)O1)C)C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506050
PubChem CID:	11251524
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

*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
NPO3171	Menisporopsis theobromae	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[15104506]
NPO3171	Menisporopsis theobromae	Species	n.a.	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
MIC	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	MIC	=	200.0	ug.mL-1	PMID[490233]

☑ 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 NPC475460 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	344
0.1-0.2	1393
0.2-0.3	2998
0.3-0.4	7465
0.4-0.5	11308
0.5-0.6	3895
0.6-0.7	5812
0.7-0.8	7102
0.8-0.85	2094
0.85-0.9	264
0.9-0.95	20
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9586	High Similarity	NPC221352
0.9521	High Similarity	NPC476684
0.9324	High Similarity	NPC309979
0.9324	High Similarity	NPC307780
0.9306	High Similarity	NPC469579
0.9122	High Similarity	NPC12305
0.911	High Similarity	NPC51106
0.911	High Similarity	NPC469542
0.9103	High Similarity	NPC67650
0.9103	High Similarity	NPC1704
0.9054	High Similarity	NPC237208
0.9041	High Similarity	NPC250755
0.9041	High Similarity	NPC474385
0.8986	High Similarity	NPC134621
0.8986	High Similarity	NPC29577
0.898	High Similarity	NPC472006
0.894	High Similarity	NPC60413
0.8919	High Similarity	NPC210425
0.8919	High Similarity	NPC277426
0.8919	High Similarity	NPC86373
0.8919	High Similarity	NPC95123
0.8919	High Similarity	NPC280404
0.8919	High Similarity	NPC66404
0.8919	High Similarity	NPC470932
0.8897	High Similarity	NPC212693
0.8897	High Similarity	NPC94248
0.8896	High Similarity	NPC146211
0.8882	High Similarity	NPC70016
0.8882	High Similarity	NPC215921
0.8874	High Similarity	NPC270160
0.8874	High Similarity	NPC237440
0.8874	High Similarity	NPC6923
0.8867	High Similarity	NPC125801
0.8861	High Similarity	NPC7752
0.8846	High Similarity	NPC472055
0.8844	High Similarity	NPC158634
0.8844	High Similarity	NPC53649
0.8844	High Similarity	NPC475730
0.8836	High Similarity	NPC32360
0.8828	High Similarity	NPC135837
0.8828	High Similarity	NPC70380
0.8824	High Similarity	NPC167903
0.8824	High Similarity	NPC273483
0.8816	High Similarity	NPC469619
0.8816	High Similarity	NPC469670
0.8808	High Similarity	NPC471642
0.8808	High Similarity	NPC35150
0.8808	High Similarity	NPC106328
0.8808	High Similarity	NPC240253
0.8808	High Similarity	NPC471641
0.8808	High Similarity	NPC240622
0.88	High Similarity	NPC267509
0.88	High Similarity	NPC163846
0.88	High Similarity	NPC107625
0.88	High Similarity	NPC225173
0.8784	High Similarity	NPC105648
0.8782	High Similarity	NPC470339
0.8776	High Similarity	NPC155205
0.8767	High Similarity	NPC472602
0.8767	High Similarity	NPC191835
0.8758	High Similarity	NPC133856
0.8758	High Similarity	NPC470569
0.8758	High Similarity	NPC478148
0.8758	High Similarity	NPC240768
0.8758	High Similarity	NPC200773
0.875	High Similarity	NPC77325
0.875	High Similarity	NPC291049
0.875	High Similarity	NPC4423
0.875	High Similarity	NPC233267
0.875	High Similarity	NPC249977
0.8742	High Similarity	NPC472036
0.8742	High Similarity	NPC210320
0.8733	High Similarity	NPC472034
0.8733	High Similarity	NPC32470
0.8725	High Similarity	NPC310340
0.8725	High Similarity	NPC471639
0.8725	High Similarity	NPC471643
0.8716	High Similarity	NPC220106
0.8716	High Similarity	NPC472604
0.8716	High Similarity	NPC472605
0.871	High Similarity	NPC149618
0.871	High Similarity	NPC89625
0.8707	High Similarity	NPC105456
0.8707	High Similarity	NPC268052
0.8707	High Similarity	NPC139634
0.8701	High Similarity	NPC474843
0.8701	High Similarity	NPC43345
0.8699	High Similarity	NPC71256
0.8693	High Similarity	NPC470568
0.869	High Similarity	NPC180905
0.869	High Similarity	NPC182496
0.8688	High Similarity	NPC477835
0.8684	High Similarity	NPC73411
0.8684	High Similarity	NPC105415
0.8684	High Similarity	NPC215711
0.8684	High Similarity	NPC2569
0.8684	High Similarity	NPC172329
0.8675	High Similarity	NPC472033
0.8675	High Similarity	NPC473023
0.8675	High Similarity	NPC25844
0.8658	High Similarity	NPC471640
0.8658	High Similarity	NPC471644
0.8658	High Similarity	NPC49108
0.8654	High Similarity	NPC227062
0.8654	High Similarity	NPC471787
0.8649	High Similarity	NPC158472
0.8649	High Similarity	NPC472600
0.8649	High Similarity	NPC472601
0.8645	High Similarity	NPC472799
0.8639	High Similarity	NPC33144
0.8639	High Similarity	NPC478200
0.8636	High Similarity	NPC227166
0.8636	High Similarity	NPC476551
0.8636	High Similarity	NPC178484
0.8636	High Similarity	NPC72958
0.8636	High Similarity	NPC204561
0.8636	High Similarity	NPC317715
0.8636	High Similarity	NPC148945
0.8636	High Similarity	NPC78835
0.8636	High Similarity	NPC309512
0.8636	High Similarity	NPC476552
0.8636	High Similarity	NPC476553
0.8636	High Similarity	NPC149526
0.8636	High Similarity	NPC232645
0.8636	High Similarity	NPC316960
0.8636	High Similarity	NPC474417
0.8634	High Similarity	NPC76647
0.863	High Similarity	NPC235115
0.8625	High Similarity	NPC469664
0.8618	High Similarity	NPC34802
0.8609	High Similarity	NPC312789
0.86	High Similarity	NPC159721
0.86	High Similarity	NPC471731
0.86	High Similarity	NPC478202
0.86	High Similarity	NPC73028
0.8599	High Similarity	NPC318527
0.8599	High Similarity	NPC324358
0.8599	High Similarity	NPC322459
0.8599	High Similarity	NPC263483
0.8599	High Similarity	NPC208258
0.8599	High Similarity	NPC323627
0.8599	High Similarity	NPC257309
0.8599	High Similarity	NPC257166
0.8591	High Similarity	NPC275734
0.8591	High Similarity	NPC472603
0.8591	High Similarity	NPC478217
0.8591	High Similarity	NPC313123
0.8591	High Similarity	NPC90411
0.859	High Similarity	NPC68727
0.859	High Similarity	NPC99381
0.859	High Similarity	NPC16082
0.859	High Similarity	NPC79375
0.859	High Similarity	NPC82592
0.859	High Similarity	NPC37253
0.8589	High Similarity	NPC477836
0.8581	High Similarity	NPC40356
0.8581	High Similarity	NPC217447
0.8581	High Similarity	NPC113608
0.8581	High Similarity	NPC268992
0.8581	High Similarity	NPC154683
0.8581	High Similarity	NPC175978
0.8581	High Similarity	NPC51824
0.8581	High Similarity	NPC87708
0.8581	High Similarity	NPC470337
0.8581	High Similarity	NPC470338
0.8571	High Similarity	NPC261292
0.8571	High Similarity	NPC147735
0.8571	High Similarity	NPC255641
0.8571	High Similarity	NPC474660
0.8571	High Similarity	NPC119929
0.8571	High Similarity	NPC301915
0.8571	High Similarity	NPC473466
0.8571	High Similarity	NPC295036
0.8571	High Similarity	NPC290954
0.8571	High Similarity	NPC194379
0.8571	High Similarity	NPC470107
0.8571	High Similarity	NPC194579
0.8562	High Similarity	NPC153417
0.8553	High Similarity	NPC187282
0.8553	High Similarity	NPC24136
0.8553	High Similarity	NPC470357
0.8553	High Similarity	NPC473927
0.8553	High Similarity	NPC138978
0.8553	High Similarity	NPC474239
0.8553	High Similarity	NPC290133
0.8552	High Similarity	NPC153783
0.8544	High Similarity	NPC15815
0.8544	High Similarity	NPC474373
0.8544	High Similarity	NPC324736
0.8544	High Similarity	NPC18699
0.8544	High Similarity	NPC51247
0.8544	High Similarity	NPC55443
0.8543	High Similarity	NPC19896
0.8543	High Similarity	NPC151607
0.8543	High Similarity	NPC42540
0.8543	High Similarity	NPC184702
0.8537	High Similarity	NPC477881
0.8535	High Similarity	NPC472050
0.8533	High Similarity	NPC476508
0.8533	High Similarity	NPC471733

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 NPC475460 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	925
0.2-0.3	1565
0.3-0.4	2525
0.4-0.5	1995
0.5-0.6	1178
0.6-0.7	446
0.7-0.8	178
0.8-0.85	35
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9139	High Similarity	NPD7819	Suspended
0.8707	High Similarity	NPD970	Clinical (unspecified phase)
0.859	High Similarity	NPD8443	Clinical (unspecified phase)
0.8516	High Similarity	NPD7411	Suspended
0.85	High Similarity	NPD6232	Discontinued
0.8457	Intermediate Similarity	NPD7473	Discontinued
0.8438	Intermediate Similarity	NPD6959	Discontinued
0.8418	Intermediate Similarity	NPD7768	Phase 2
0.8408	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD2533	Approved
0.8366	Intermediate Similarity	NPD2532	Approved
0.8366	Intermediate Similarity	NPD2534	Approved
0.8365	Intermediate Similarity	NPD7075	Discontinued
0.8322	Intermediate Similarity	NPD2796	Approved
0.8302	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD1510	Phase 2
0.8242	Intermediate Similarity	NPD5844	Phase 1
0.8239	Intermediate Similarity	NPD3817	Phase 2
0.8228	Intermediate Similarity	NPD6801	Discontinued
0.8219	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD4380	Phase 2
0.8212	Intermediate Similarity	NPD1549	Phase 2
0.8182	Intermediate Similarity	NPD6799	Approved
0.8176	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6166	Phase 2
0.8137	Intermediate Similarity	NPD3749	Approved
0.8129	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD1934	Approved
0.8108	Intermediate Similarity	NPD1240	Approved
0.8105	Intermediate Similarity	NPD3750	Approved
0.8101	Intermediate Similarity	NPD6599	Discontinued
0.8039	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD3748	Approved
0.8	Intermediate Similarity	NPD1607	Approved
0.7988	Intermediate Similarity	NPD7199	Phase 2
0.7976	Intermediate Similarity	NPD7472	Approved
0.7976	Intermediate Similarity	NPD7074	Phase 3
0.7961	Intermediate Similarity	NPD2935	Discontinued
0.7941	Intermediate Similarity	NPD7808	Phase 3
0.7925	Intermediate Similarity	NPD3226	Approved
0.7917	Intermediate Similarity	NPD7054	Approved
0.7917	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD5403	Approved
0.7901	Intermediate Similarity	NPD5402	Approved
0.7898	Intermediate Similarity	NPD5401	Approved
0.7898	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD37	Approved
0.7886	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7251	Discontinued
0.7871	Intermediate Similarity	NPD4628	Phase 3
0.7857	Intermediate Similarity	NPD3818	Discontinued
0.7853	Intermediate Similarity	NPD4967	Phase 2
0.7853	Intermediate Similarity	NPD4966	Approved
0.7853	Intermediate Similarity	NPD4965	Approved
0.7843	Intermediate Similarity	NPD1551	Phase 2
0.784	Intermediate Similarity	NPD2801	Approved
0.7838	Intermediate Similarity	NPD6832	Phase 2
0.7834	Intermediate Similarity	NPD7390	Discontinued
0.7834	Intermediate Similarity	NPD1511	Approved
0.7831	Intermediate Similarity	NPD7229	Phase 3
0.7824	Intermediate Similarity	NPD6797	Phase 2
0.7812	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD8312	Approved
0.7791	Intermediate Similarity	NPD8313	Approved
0.7784	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6559	Discontinued
0.7778	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD3882	Suspended
0.7736	Intermediate Similarity	NPD1512	Approved
0.7733	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD8151	Discontinued
0.773	Intermediate Similarity	NPD1465	Phase 2
0.7725	Intermediate Similarity	NPD5710	Approved
0.7725	Intermediate Similarity	NPD5711	Approved
0.7711	Intermediate Similarity	NPD5494	Approved
0.7692	Intermediate Similarity	NPD1243	Approved
0.7677	Intermediate Similarity	NPD2346	Discontinued
0.767	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2799	Discontinued
0.7662	Intermediate Similarity	NPD7033	Discontinued
0.7651	Intermediate Similarity	NPD6234	Discontinued
0.7647	Intermediate Similarity	NPD6651	Approved
0.7643	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6273	Approved
0.7622	Intermediate Similarity	NPD8455	Phase 2
0.7616	Intermediate Similarity	NPD3764	Approved
0.7613	Intermediate Similarity	NPD6100	Approved
0.7613	Intermediate Similarity	NPD5406	Approved
0.7613	Intermediate Similarity	NPD5404	Approved
0.7613	Intermediate Similarity	NPD6099	Approved
0.7613	Intermediate Similarity	NPD5408	Approved
0.7613	Intermediate Similarity	NPD5405	Approved
0.761	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD920	Approved
0.7551	Intermediate Similarity	NPD1608	Approved
0.7547	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7228	Approved
0.7532	Intermediate Similarity	NPD7003	Approved
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.7514	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6798	Discontinued
0.7483	Intermediate Similarity	NPD4908	Phase 1
0.7471	Intermediate Similarity	NPD7240	Approved
0.7471	Intermediate Similarity	NPD3926	Phase 2
0.7468	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2800	Approved
0.7468	Intermediate Similarity	NPD230	Phase 1
0.7467	Intermediate Similarity	NPD2798	Approved
0.7458	Intermediate Similarity	NPD8434	Phase 2
0.7458	Intermediate Similarity	NPD8150	Discontinued
0.7453	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD919	Approved
0.7412	Intermediate Similarity	NPD3787	Discontinued
0.74	Intermediate Similarity	NPD1203	Approved
0.74	Intermediate Similarity	NPD2797	Approved
0.7399	Intermediate Similarity	NPD7286	Phase 2
0.7386	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3268	Approved
0.7386	Intermediate Similarity	NPD2313	Discontinued
0.7378	Intermediate Similarity	NPD7458	Discontinued
0.7368	Intermediate Similarity	NPD7783	Phase 2
0.7368	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7435	Discontinued
0.7365	Intermediate Similarity	NPD4288	Approved
0.7355	Intermediate Similarity	NPD6355	Discontinued
0.7347	Intermediate Similarity	NPD17	Approved
0.7342	Intermediate Similarity	NPD2344	Approved
0.7341	Intermediate Similarity	NPD7177	Discontinued
0.7341	Intermediate Similarity	NPD3751	Discontinued
0.7333	Intermediate Similarity	NPD1283	Approved
0.733	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7870	Phase 2
0.7326	Intermediate Similarity	NPD7871	Phase 2
0.7315	Intermediate Similarity	NPD9717	Approved
0.7303	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD943	Approved
0.7289	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2438	Suspended
0.7278	Intermediate Similarity	NPD6971	Discontinued
0.7273	Intermediate Similarity	NPD7697	Approved
0.7273	Intermediate Similarity	NPD7696	Phase 3
0.7273	Intermediate Similarity	NPD7698	Approved
0.7267	Intermediate Similarity	NPD6190	Approved
0.7251	Intermediate Similarity	NPD8127	Discontinued
0.725	Intermediate Similarity	NPD2654	Approved
0.7248	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1201	Approved
0.7244	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5124	Phase 1
0.7241	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6233	Phase 2
0.7225	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7874	Approved
0.7215	Intermediate Similarity	NPD4308	Phase 3
0.7211	Intermediate Similarity	NPD9545	Approved
0.7204	Intermediate Similarity	NPD6776	Approved
0.7204	Intermediate Similarity	NPD6781	Approved
0.7204	Intermediate Similarity	NPD6777	Approved
0.7204	Intermediate Similarity	NPD6782	Approved
0.7204	Intermediate Similarity	NPD6778	Approved
0.7204	Intermediate Similarity	NPD6780	Approved
0.7204	Intermediate Similarity	NPD6779	Approved
0.7193	Intermediate Similarity	NPD6746	Phase 2
0.7182	Intermediate Similarity	NPD4287	Approved
0.7179	Intermediate Similarity	NPD2979	Phase 3
0.7175	Intermediate Similarity	NPD7685	Pre-registration
0.7171	Intermediate Similarity	NPD3266	Approved
0.7171	Intermediate Similarity	NPD1470	Approved
0.7171	Intermediate Similarity	NPD3267	Approved
0.717	Intermediate Similarity	NPD4476	Approved
0.717	Intermediate Similarity	NPD4477	Approved
0.7168	Intermediate Similarity	NPD5242	Approved
0.7162	Intermediate Similarity	NPD5691	Approved
0.7161	Intermediate Similarity	NPD411	Approved
0.7161	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2309	Approved
0.716	Intermediate Similarity	NPD5353	Approved
0.7134	Intermediate Similarity	NPD447	Suspended
0.7134	Intermediate Similarity	NPD1933	Approved
0.7134	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1610	Phase 2
0.7133	Intermediate Similarity	NPD422	Phase 1
0.7133	Intermediate Similarity	NPD1281	Approved
0.7124	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7701	Phase 2
0.7115	Intermediate Similarity	NPD8032	Phase 2
0.7114	Intermediate Similarity	NPD4626	Approved
0.7112	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3225	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