NPASS Compound

Structure

NPC307642 OpenBabel07101719512D 74 81 0 0 1 0 0 0 0 0999 V2000 12.3989 -1.6922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7590 -3.3864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4426 -2.1080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3820 -3.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8027 -3.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8245 -4.0102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1306 -6.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1847 -5.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0899 -2.6433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1117 -2.8512 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.5155 -4.9612 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5374 -5.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1361 -5.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -6.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 -5.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -6.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.8756 -6.6554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4670 -6.7213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 6 7 2 0 0 0 0 6 21 1 0 0 0 0 8 9 1 0 0 0 0 9 25 2 0 0 0 0 10 12 1 0 0 0 0 10 24 1 0 0 0 0 11 13 1 0 0 0 0 11 29 1 0 0 0 0 12 51 1 0 0 0 0 13 50 1 0 0 0 0 14 26 1 0 0 0 0 14 27 1 0 0 0 0 15 22 1 0 0 0 0 15 52 1 0 0 0 0 16 53 1 0 0 0 0 17 54 1 0 0 0 0 18 55 1 0 0 0 0 19 28 1 0 0 0 0 19 67 1 0 0 0 0 20 21 1 0 0 0 0 21 3 1 1 0 0 0 22 7 1 1 0 0 0 22 26 1 0 0 0 0 23 8 1 6 0 0 0 23 24 1 0 0 0 0 23 33 1 0 0 0 0 24 50 1 1 0 0 0 25 34 1 0 0 0 0 25 50 1 0 0 0 0 26 51 1 1 0 0 0 27 33 1 0 0 0 0 27 56 1 6 0 0 0 28 35 1 0 0 0 0 28 57 1 6 0 0 0 29 34 1 0 0 0 0 29 68 1 1 0 0 0 30 16 1 6 0 0 0 30 36 1 0 0 0 0 30 69 1 0 0 0 0 31 17 1 1 0 0 0 31 37 1 0 0 0 0 31 70 1 0 0 0 0 32 18 1 6 0 0 0 32 43 1 0 0 0 0 32 71 1 0 0 0 0 33 51 1 1 0 0 0 34 58 1 1 0 0 0 35 45 1 0 0 0 0 35 59 1 6 0 0 0 36 38 1 0 0 0 0 36 60 1 6 0 0 0 37 39 1 0 0 0 0 37 61 1 1 0 0 0 38 40 1 0 0 0 0 38 62 1 6 0 0 0 39 41 1 0 0 0 0 39 63 1 1 0 0 0 40 46 1 0 0 0 0 40 64 1 1 0 0 0 41 47 1 0 0 0 0 41 65 1 6 0 0 0 42 44 1 0 0 0 0 42 48 1 0 0 0 0 42 66 1 1 0 0 0 43 44 1 0 0 0 0 43 72 1 1 0 0 0 44 73 1 6 0 0 0 45 49 1 0 0 0 0 45 74 1 1 0 0 0 46 69 1 0 0 0 0 46 72 1 6 0 0 0 47 70 1 0 0 0 0 47 74 1 6 0 0 0 48 68 1 6 0 0 0 48 71 1 0 0 0 0 49 67 1 0 0 0 0 49 73 1 1 0 0 0 50 4 1 1 0 0 0 51 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1064.54
Volume:	1019.102
LogP:	0.243
LogD:	0.77
LogS:	-2.387
# Rotatable Bonds:	16
TPSA:	377.29
# H-Bond Aceptor:	23
# H-Bond Donor:	15
# Rings:	8
# Heavy Atoms:	23

MedChem Properties

QED Drug-Likeness Score:	0.066
Synthetic Accessibility Score:	6.949
Fsp3:	0.922
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.368
MDCK Permeability:	0.000433189095929265
Pgp-inhibitor:	0.011
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	76.68671417236328%
Volume Distribution (VD):	-0.171
Pgp-substrate:	17.37151527404785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.009
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.005

ADMET: Excretion

Clearance (CL):	0.097
Half-life (T1/2):	0.642

ADMET: Toxicity

hERG Blockers:	0.23
Human Hepatotoxicity (H-HT):	0.314
Drug-inuced Liver Injury (DILI):	0.527
AMES Toxicity:	0.077
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.12
Carcinogencity:	0.013
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.091

Download Data

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

Natural Product: NPC307642

Natural Product ID:	NPC307642
*Common Name:**	Mycaloside A
IUPAC Name:	(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-6-[[(3S,4R,8R,9S,10R,13R,14S,15S,17R)-4,15-dihydroxy-17-[(E,2R,5S)-1-hydroxy-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4-[(2S,3S,4R,5R)-4,5-dihydroxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	PLPPDJYJWQKNNL-AUVXDXBKSA-N
Standard InCHI:	InChI=1S/C51H84O23/c1-20(2)21(3)6-7-22(15-52)26-14-27(56)33-23-8-9-25-34(58)29(11-13-50(25,4)24(23)10-12-51(26,33)5)68-48-42(66)44(43(32(18-55)71-48)72-46-40(64)38(62)36(60)30(16-53)69-46)73-49-45(35(59)28(57)19-67-49)74-47-41(65)39(63)37(61)31(17-54)70-47/h6-7,9,20-24,26-49,52-66H,8,10-19H2,1-5H3/b7-6+/t21-,22+,23-,24+,26-,27+,28-,29+,30-,31-,32-,33-,34-,35-,36+,37+,38+,39+,40-,41-,42-,43-,44-,45+,46+,47-,48-,49+,50-,51-/m1/s1
SMILES:	CC(C)[C@H](C)/C=C/[C@@H](CO)[C@H]1C[C@@H]([C@H]2[C@@H]3CC=C4[C@H]([C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O)O[C@H]1[C@H]([C@@H]([C@@H](CO1)O)O)O[C@@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503906
PubChem CID:	21637455
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal 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
NPO15579	Mycale laxissima	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932129]
NPO15579	Mycale laxissima	Species	Mycalidae	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
EC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		EC50	=	3.2	ug.mL-1	PMID[458646]

☑ 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 NPC307642 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	293
0.1-0.2	1923
0.2-0.3	5650
0.3-0.4	13152
0.4-0.5	9921
0.5-0.6	6051
0.6-0.7	3226
0.7-0.8	1589
0.8-0.85	504
0.85-0.9	279
0.9-0.95	108
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9434	High Similarity	NPC476547
0.9423	High Similarity	NPC94272
0.9346	High Similarity	NPC32361
0.9346	High Similarity	NPC210569
0.9346	High Similarity	NPC244431
0.9346	High Similarity	NPC31896
0.9346	High Similarity	NPC263359
0.934	High Similarity	NPC141433
0.9259	High Similarity	NPC79900
0.9259	High Similarity	NPC476546
0.9245	High Similarity	NPC218571
0.9245	High Similarity	NPC171073
0.9245	High Similarity	NPC475333
0.9245	High Similarity	NPC150372
0.9245	High Similarity	NPC208383
0.9245	High Similarity	NPC248746
0.9245	High Similarity	NPC73243
0.9245	High Similarity	NPC84956
0.9245	High Similarity	NPC22779
0.9245	High Similarity	NPC244086
0.9245	High Similarity	NPC300557
0.9245	High Similarity	NPC470433
0.9245	High Similarity	NPC475550
0.9245	High Similarity	NPC224098
0.9245	High Similarity	NPC102016
0.9245	High Similarity	NPC249265
0.9245	High Similarity	NPC194207
0.9245	High Similarity	NPC477809
0.9245	High Similarity	NPC309278
0.9245	High Similarity	NPC95051
0.9245	High Similarity	NPC46190
0.9245	High Similarity	NPC232054
0.9245	High Similarity	NPC6806
0.9174	High Similarity	NPC32707
0.9174	High Similarity	NPC208832
0.9174	High Similarity	NPC167183
0.9167	High Similarity	NPC472716
0.9167	High Similarity	NPC42171
0.9159	High Similarity	NPC477811
0.9159	High Similarity	NPC269297
0.9159	High Similarity	NPC222202
0.9159	High Similarity	NPC224314
0.9159	High Similarity	NPC23808
0.9159	High Similarity	NPC87998
0.9151	High Similarity	NPC98696
0.9143	High Similarity	NPC242748
0.9091	High Similarity	NPC146652
0.9074	High Similarity	NPC13193
0.9074	High Similarity	NPC475247
0.9074	High Similarity	NPC294129
0.9074	High Similarity	NPC477032
0.9074	High Similarity	NPC472715
0.9074	High Similarity	NPC477028
0.9074	High Similarity	NPC124677
0.9065	High Similarity	NPC302057
0.9057	High Similarity	NPC14704
0.9057	High Similarity	NPC230507
0.9057	High Similarity	NPC190395
0.9057	High Similarity	NPC113044
0.9057	High Similarity	NPC161676
0.9057	High Similarity	NPC283829
0.9057	High Similarity	NPC470432
0.9057	High Similarity	NPC305423
0.9048	High Similarity	NPC75608
0.9038	High Similarity	NPC272015
0.9	High Similarity	NPC477810
0.9	High Similarity	NPC11548
0.8991	High Similarity	NPC308140
0.8981	High Similarity	NPC247037
0.8981	High Similarity	NPC472717
0.8972	High Similarity	NPC472897
0.8972	High Similarity	NPC472896
0.8972	High Similarity	NPC180183
0.8972	High Similarity	NPC246124
0.8962	High Similarity	NPC309448
0.8962	High Similarity	NPC181845
0.8962	High Similarity	NPC473923
0.8962	High Similarity	NPC473476
0.8962	High Similarity	NPC474569
0.8942	High Similarity	NPC470434
0.8938	High Similarity	NPC129393
0.8919	High Similarity	NPC477030
0.8919	High Similarity	NPC477029
0.8909	High Similarity	NPC469347
0.8909	High Similarity	NPC51154
0.8909	High Similarity	NPC469348
0.8899	High Similarity	NPC470748
0.8899	High Similarity	NPC197231
0.8889	High Similarity	NPC477027
0.8889	High Similarity	NPC70204
0.8889	High Similarity	NPC477026
0.8889	High Similarity	NPC475670
0.8889	High Similarity	NPC40440
0.8889	High Similarity	NPC42482
0.8889	High Similarity	NPC306131
0.8879	High Similarity	NPC63368
0.8879	High Similarity	NPC473469
0.8879	High Similarity	NPC208650
0.8879	High Similarity	NPC231340
0.8879	High Similarity	NPC14946
0.8879	High Similarity	NPC181467
0.8868	High Similarity	NPC470885
0.8868	High Similarity	NPC187400
0.8868	High Similarity	NPC221562
0.8846	High Similarity	NPC469942
0.8839	High Similarity	NPC20979
0.8829	High Similarity	NPC477808
0.8818	High Similarity	NPC473567
0.8818	High Similarity	NPC254255
0.8818	High Similarity	NPC216595
0.8818	High Similarity	NPC112274
0.8818	High Similarity	NPC19888
0.8796	High Similarity	NPC6931
0.8796	High Similarity	NPC159005
0.8796	High Similarity	NPC476538
0.8796	High Similarity	NPC476539
0.8796	High Similarity	NPC476540
0.8796	High Similarity	NPC476541
0.8796	High Similarity	NPC7213
0.8796	High Similarity	NPC295980
0.8785	High Similarity	NPC160816
0.8785	High Similarity	NPC194842
0.8785	High Similarity	NPC208477
0.8785	High Similarity	NPC472899
0.8785	High Similarity	NPC472900
0.8785	High Similarity	NPC69737
0.8785	High Similarity	NPC127801
0.8785	High Similarity	NPC472898
0.8785	High Similarity	NPC152584
0.8785	High Similarity	NPC208594
0.8785	High Similarity	NPC269627
0.8774	High Similarity	NPC16573
0.8774	High Similarity	NPC473198
0.8772	High Similarity	NPC50689
0.8772	High Similarity	NPC473566
0.8772	High Similarity	NPC475358
0.8761	High Similarity	NPC10366
0.875	High Similarity	NPC63609
0.875	High Similarity	NPC158088
0.875	High Similarity	NPC477031
0.875	High Similarity	NPC148965
0.8739	High Similarity	NPC476693
0.8727	High Similarity	NPC114188
0.8727	High Similarity	NPC92710
0.8727	High Similarity	NPC13190
0.8716	High Similarity	NPC157530
0.8716	High Similarity	NPC250089
0.8716	High Similarity	NPC14630
0.8716	High Similarity	NPC151134
0.8704	High Similarity	NPC33053
0.8692	High Similarity	NPC165033
0.8692	High Similarity	NPC148603
0.8692	High Similarity	NPC312774
0.8692	High Similarity	NPC93352
0.8692	High Similarity	NPC273879
0.8684	High Similarity	NPC229962
0.8684	High Similarity	NPC473633
0.8684	High Similarity	NPC476085
0.8684	High Similarity	NPC195560
0.8679	High Similarity	NPC288694
0.8679	High Similarity	NPC312553
0.8679	High Similarity	NPC159036
0.8673	High Similarity	NPC477807
0.8673	High Similarity	NPC476690
0.8673	High Similarity	NPC100048
0.8667	High Similarity	NPC91497
0.8667	High Similarity	NPC282669
0.8667	High Similarity	NPC64348
0.8654	High Similarity	NPC243728
0.8654	High Similarity	NPC473890
0.8649	High Similarity	NPC477050
0.8649	High Similarity	NPC475312
0.8636	High Similarity	NPC470867
0.8624	High Similarity	NPC128123
0.8624	High Similarity	NPC51172
0.8624	High Similarity	NPC220427
0.8624	High Similarity	NPC125324
0.8624	High Similarity	NPC49032
0.8624	High Similarity	NPC235824
0.8624	High Similarity	NPC126147
0.8611	High Similarity	NPC173859
0.8611	High Similarity	NPC26798
0.8611	High Similarity	NPC470512
0.8609	High Similarity	NPC198325
0.8609	High Similarity	NPC233391
0.8609	High Similarity	NPC207243
0.8598	High Similarity	NPC16520
0.8598	High Similarity	NPC473020
0.8598	High Similarity	NPC8039
0.8598	High Similarity	NPC123796
0.8598	High Similarity	NPC31907
0.8598	High Similarity	NPC472252
0.8598	High Similarity	NPC245280
0.8598	High Similarity	NPC120123
0.8598	High Similarity	NPC286969
0.8598	High Similarity	NPC157659
0.8598	High Similarity	NPC162354
0.8598	High Similarity	NPC155010
0.8598	High Similarity	NPC189852
0.8598	High Similarity	NPC131479

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 NPC307642 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	1994
0.2-0.3	4197
0.3-0.4	1835
0.4-0.5	490
0.5-0.6	266
0.6-0.7	101
0.7-0.8	15
0.8-0.85	9
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8291	Intermediate Similarity	NPD8377	Approved
0.8291	Intermediate Similarity	NPD8294	Approved
0.822	Intermediate Similarity	NPD8378	Approved
0.822	Intermediate Similarity	NPD8296	Approved
0.822	Intermediate Similarity	NPD8335	Approved
0.822	Intermediate Similarity	NPD8033	Approved
0.822	Intermediate Similarity	NPD8380	Approved
0.822	Intermediate Similarity	NPD8379	Approved
0.7917	Intermediate Similarity	NPD7503	Approved
0.7899	Intermediate Similarity	NPD7516	Approved
0.7815	Intermediate Similarity	NPD7327	Approved
0.7815	Intermediate Similarity	NPD7328	Approved
0.7778	Intermediate Similarity	NPD8133	Approved
0.7757	Intermediate Similarity	NPD8171	Discontinued
0.7719	Intermediate Similarity	NPD6412	Phase 2
0.7656	Intermediate Similarity	NPD8450	Suspended
0.7578	Intermediate Similarity	NPD8449	Approved
0.7381	Intermediate Similarity	NPD7507	Approved
0.7288	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7319	Approved
0.72	Intermediate Similarity	NPD8515	Approved
0.72	Intermediate Similarity	NPD8517	Approved
0.72	Intermediate Similarity	NPD8516	Approved
0.713	Intermediate Similarity	NPD7524	Approved
0.7094	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD8328	Phase 3
0.7063	Intermediate Similarity	NPD8513	Phase 3
0.7059	Intermediate Similarity	NPD6686	Approved
0.7016	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6370	Approved
0.7	Intermediate Similarity	NPD7736	Approved
0.6972	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6054	Approved
0.6794	Remote Similarity	NPD8293	Discontinued
0.6759	Remote Similarity	NPD6695	Phase 3
0.6752	Remote Similarity	NPD7639	Approved
0.6752	Remote Similarity	NPD7640	Approved
0.6731	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6059	Approved
0.6694	Remote Similarity	NPD8297	Approved
0.6694	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD7750	Discontinued
0.6643	Remote Similarity	NPD7625	Phase 1
0.6641	Remote Similarity	NPD7492	Approved
0.6636	Remote Similarity	NPD6928	Phase 2
0.6636	Remote Similarity	NPD7525	Registered
0.6635	Remote Similarity	NPD7339	Approved
0.6635	Remote Similarity	NPD6942	Approved
0.6615	Remote Similarity	NPD5988	Approved
0.6614	Remote Similarity	NPD7115	Discovery
0.6614	Remote Similarity	NPD6009	Approved
0.6591	Remote Similarity	NPD6616	Approved
0.6589	Remote Similarity	NPD6319	Approved
0.6565	Remote Similarity	NPD6067	Discontinued
0.6542	Remote Similarity	NPD7645	Phase 2
0.6542	Remote Similarity	NPD6929	Approved
0.6541	Remote Similarity	NPD7078	Approved
0.6508	Remote Similarity	NPD4632	Approved
0.6481	Remote Similarity	NPD7514	Phase 3
0.6481	Remote Similarity	NPD6931	Approved
0.6481	Remote Similarity	NPD6930	Phase 2
0.6449	Remote Similarity	NPD7145	Approved
0.6435	Remote Similarity	NPD7637	Suspended
0.6422	Remote Similarity	NPD6902	Approved
0.6417	Remote Similarity	NPD4159	Approved
0.6381	Remote Similarity	NPD4784	Approved
0.6381	Remote Similarity	NPD4785	Approved
0.6379	Remote Similarity	NPD6399	Phase 3
0.6371	Remote Similarity	NPD6899	Approved
0.6371	Remote Similarity	NPD6881	Approved
0.6364	Remote Similarity	NPD5211	Phase 2
0.6355	Remote Similarity	NPD6925	Approved
0.6355	Remote Similarity	NPD5776	Phase 2
0.6349	Remote Similarity	NPD6649	Approved
0.6349	Remote Similarity	NPD8130	Phase 1
0.6349	Remote Similarity	NPD6650	Approved
0.6341	Remote Similarity	NPD7128	Approved
0.6341	Remote Similarity	NPD6675	Approved
0.6341	Remote Similarity	NPD5739	Approved
0.6341	Remote Similarity	NPD6402	Approved
0.633	Remote Similarity	NPD7332	Phase 2
0.632	Remote Similarity	NPD6373	Approved
0.632	Remote Similarity	NPD6372	Approved
0.6293	Remote Similarity	NPD7087	Discontinued
0.629	Remote Similarity	NPD5697	Approved
0.6281	Remote Similarity	NPD5344	Discontinued
0.627	Remote Similarity	NPD7102	Approved
0.627	Remote Similarity	NPD7290	Approved
0.627	Remote Similarity	NPD4634	Approved
0.627	Remote Similarity	NPD6883	Approved
0.6262	Remote Similarity	NPD6933	Approved
0.6261	Remote Similarity	NPD6051	Approved
0.626	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD6033	Approved
0.625	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD4786	Approved
0.624	Remote Similarity	NPD7320	Approved
0.623	Remote Similarity	NPD7632	Discontinued
0.622	Remote Similarity	NPD6847	Approved
0.622	Remote Similarity	NPD6617	Approved
0.622	Remote Similarity	NPD6869	Approved
0.6204	Remote Similarity	NPD6932	Approved
0.6198	Remote Similarity	NPD5286	Approved
0.6198	Remote Similarity	NPD5285	Approved
0.6198	Remote Similarity	NPD4696	Approved
0.6195	Remote Similarity	NPD6893	Approved
0.6194	Remote Similarity	NPD7604	Phase 2
0.619	Remote Similarity	NPD6014	Approved
0.619	Remote Similarity	NPD6012	Approved
0.619	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6013	Approved
0.619	Remote Similarity	NPD4243	Approved
0.6182	Remote Similarity	NPD4748	Discontinued
0.6176	Remote Similarity	NPD8074	Phase 3
0.6168	Remote Similarity	NPD8264	Approved
0.6167	Remote Similarity	NPD6084	Phase 2
0.6167	Remote Similarity	NPD4755	Approved
0.6167	Remote Similarity	NPD6083	Phase 2
0.6165	Remote Similarity	NPD5983	Phase 2
0.616	Remote Similarity	NPD5701	Approved
0.6111	Remote Similarity	NPD6011	Approved
0.6103	Remote Similarity	NPD6336	Discontinued
0.6102	Remote Similarity	NPD4202	Approved
0.6098	Remote Similarity	NPD5226	Approved
0.6098	Remote Similarity	NPD4633	Approved
0.6098	Remote Similarity	NPD5225	Approved
0.6098	Remote Similarity	NPD5224	Approved
0.608	Remote Similarity	NPD6008	Approved
0.6075	Remote Similarity	NPD6926	Approved
0.6075	Remote Similarity	NPD6924	Approved
0.6071	Remote Similarity	NPD3667	Approved
0.6066	Remote Similarity	NPD4700	Approved
0.605	Remote Similarity	NPD7748	Approved
0.6048	Remote Similarity	NPD5174	Approved
0.6048	Remote Similarity	NPD5175	Approved
0.6047	Remote Similarity	NPD6053	Discontinued
0.6047	Remote Similarity	NPD6430	Approved
0.6047	Remote Similarity	NPD6429	Approved
0.6043	Remote Similarity	NPD5956	Approved
0.6038	Remote Similarity	NPD7152	Approved
0.6038	Remote Similarity	NPD7150	Approved
0.6038	Remote Similarity	NPD7151	Approved
0.6033	Remote Similarity	NPD7902	Approved
0.6017	Remote Similarity	NPD6079	Approved
0.6017	Remote Similarity	NPD8034	Phase 2
0.6017	Remote Similarity	NPD8035	Phase 2
0.6016	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD7991	Discontinued
0.6	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD4729	Approved
0.5984	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD4730	Approved
0.5983	Remote Similarity	NPD5328	Approved
0.5983	Remote Similarity	NPD4753	Phase 2
0.5982	Remote Similarity	NPD6898	Phase 1
0.5969	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD3666	Approved
0.5965	Remote Similarity	NPD3133	Approved
0.5965	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD3665	Phase 1
0.5952	Remote Similarity	NPD4767	Approved
0.5952	Remote Similarity	NPD4768	Approved
0.5952	Remote Similarity	NPD6640	Phase 3
0.5948	Remote Similarity	NPD4250	Approved
0.5948	Remote Similarity	NPD4251	Approved
0.5946	Remote Similarity	NPD4195	Approved
0.5946	Remote Similarity	NPD6683	Phase 2
0.5943	Remote Similarity	NPD7143	Approved
0.5943	Remote Similarity	NPD7144	Approved
0.5935	Remote Similarity	NPD6648	Approved
0.5932	Remote Similarity	NPD3168	Discontinued
0.5932	Remote Similarity	NPD7838	Discovery
0.5897	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD7101	Approved
0.5896	Remote Similarity	NPD7100	Approved
0.5893	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD7509	Discontinued
0.5891	Remote Similarity	NPD5250	Approved
0.5891	Remote Similarity	NPD5248	Approved
0.5891	Remote Similarity	NPD5249	Phase 3
0.5891	Remote Similarity	NPD5251	Approved
0.5891	Remote Similarity	NPD5247	Approved
0.5882	Remote Similarity	NPD5126	Approved
0.5882	Remote Similarity	NPD5125	Phase 3
0.5882	Remote Similarity	NPD7515	Phase 2
0.5882	Remote Similarity	NPD7983	Approved
0.5872	Remote Similarity	NPD5275	Approved
0.5872	Remote Similarity	NPD4190	Phase 3
0.5868	Remote Similarity	NPD5210	Approved
0.5868	Remote Similarity	NPD4629	Approved
0.5868	Remote Similarity	NPD5695	Phase 3
0.5862	Remote Similarity	NPD5330	Approved
0.5862	Remote Similarity	NPD3618	Phase 1

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