NPASS Compound

Structure

CID60849 OpenBabel06191715392D 77 82 0 0 1 0 0 0 0 0999 V2000 -0.2041 -4.9868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6348 6.1945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8187 8.1860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3966 7.0193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4043 -3.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3166 3.9977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1854 6.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9147 1.4977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6790 -4.1068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8381 -2.6838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0087 -3.2423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5098 -1.9429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0696 -3.5862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9847 -1.0629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0756 -3.6953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2352 -0.0948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6786 -4.0780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0844 -3.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2467 0.9052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4086 3.5889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8184 6.7720 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.9104 7.7677 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9881 6.2130 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8602 -2.6516 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3166 2.9977 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0935 5.5172 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9147 2.4977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1535 -3.1980 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7369 2.8481 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0186 1.8788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9821 6.3221 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3147 -1.7609 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1369 2.9798 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5736 5.5158 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7705 -0.9219 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7846 2.3788 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1827 1.4977 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3166 0.9977 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.8179 3.9439 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1827 2.4977 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9099 4.9397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1711 4.6004 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2281 -0.9736 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7186 1.4977 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9096 3.5256 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9101 6.3537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4506 1.4977 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1771 4.4913 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6826 -1.8644 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0932 4.1031 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0115 0.9999 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.0940 8.3452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7807 2.9977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9576 2.2226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3846 7.2375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3133 -1.7091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4316 3.9354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5676 5.6249 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2250 -0.0311 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7155 2.7441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0487 0.9977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3166 -0.0023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6343 3.3664 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0937 6.9312 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2380 4.1475 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5856 5.2976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1385 -2.7034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4506 2.4977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1851 5.0989 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0487 2.9977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3371 -2.6205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2620 1.9681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5641 2.7695 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8182 5.3579 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5846 0.9977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1623 4.4685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 8 27 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 18 28 1 0 0 0 0 19 30 1 0 0 0 0 20 65 1 0 0 0 0 21 2 1 6 0 0 0 21 22 1 0 0 0 0 21 46 1 0 0 0 0 22 3 1 1 0 0 0 22 52 1 0 0 0 0 23 4 1 1 0 0 0 23 31 1 0 0 0 0 23 66 1 0 0 0 0 24 5 1 1 0 0 0 24 32 1 0 0 0 0 24 67 1 0 0 0 0 25 6 1 1 0 0 0 25 40 1 0 0 0 0 25 68 1 0 0 0 0 26 7 1 6 0 0 0 26 41 1 0 0 0 0 26 69 1 0 0 0 0 27 53 2 0 0 0 0 27 70 1 0 0 0 0 28 17 1 1 0 0 0 28 71 1 0 0 0 0 29 20 1 6 0 0 0 29 33 1 0 0 0 0 29 72 1 0 0 0 0 30 54 2 0 0 0 0 30 73 1 0 0 0 0 31 34 1 0 0 0 0 31 55 1 6 0 0 0 32 35 1 0 0 0 0 32 56 1 6 0 0 0 33 36 1 0 0 0 0 33 57 1 1 0 0 0 34 42 1 0 0 0 0 34 58 1 1 0 0 0 35 43 1 0 0 0 0 35 59 1 1 0 0 0 36 44 1 0 0 0 0 36 60 1 6 0 0 0 37 38 1 0 0 0 0 37 40 1 0 0 0 0 37 61 1 1 0 0 0 38 47 1 0 0 0 0 38 62 1 1 0 0 0 39 41 1 0 0 0 0 39 45 1 0 0 0 0 39 63 1 6 0 0 0 40 70 1 6 0 0 0 41 74 1 1 0 0 0 42 48 1 0 0 0 0 42 76 1 6 0 0 0 43 49 1 0 0 0 0 43 77 1 6 0 0 0 44 51 1 0 0 0 0 44 75 1 1 0 0 0 45 50 1 0 0 0 0 45 73 1 6 0 0 0 46 64 2 0 0 0 0 46 74 1 0 0 0 0 47 68 1 0 0 0 0 47 75 1 6 0 0 0 48 65 1 1 0 0 0 48 66 1 0 0 0 0 49 67 1 1 0 0 0 49 71 1 0 0 0 0 50 69 1 1 0 0 0 50 76 1 0 0 0 0 51 72 1 6 0 0 0 51 77 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1114.54
Volume:	1059.949
LogP:	3.06
LogD:	2.071
LogS:	-3.398
# Rotatable Bonds:	10
TPSA:	373.5
# H-Bond Aceptor:	26
# H-Bond Donor:	10
# Rings:	6
# Heavy Atoms:	26

MedChem Properties

QED Drug-Likeness Score:	0.099
Synthetic Accessibility Score:	7.982
Fsp3:	0.941
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:	-6.106
MDCK Permeability:	0.0006641680956818163
Pgp-inhibitor:	0.073
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.993
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	62.728885650634766%
Volume Distribution (VD):	0.296
Pgp-substrate:	10.996176719665527%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.055
CYP2D6-substrate:	0.018
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.009

ADMET: Excretion

Clearance (CL):	0.645
Half-life (T1/2):	0.807

ADMET: Toxicity

hERG Blockers:	0.885
Human Hepatotoxicity (H-HT):	0.586
Drug-inuced Liver Injury (DILI):	0.879
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.068
Maximum Recommended Daily Dose:	0.0
Skin Sensitization:	0.184
Carcinogencity:	0.081
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.118

Download Data

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

Natural Product: NPC60849

Natural Product ID:	NPC60849
*Common Name:**	Albinoside I
IUPAC Name:	n.a.
Synonyms:	Albinoside I
Standard InCHIKey:	IZXAJJIHCIQBDV-QZAYOBNPSA-N
Standard InCHI:	InChI=1S/C51H86O26/c1-9-17-28-18-15-13-11-10-12-14-16-19-30(54)73-45-39(63)41(74-46(64)21(2)22(3)52)26(7)69-50(45)76-42-34(58)31(55)23(4)66-48(42)65-20-29-33(57)36(60)44(75-47-38(62)37(61)40(25(6)68-47)70-27(8)53)51(72-29)77-43-35(59)32(56)24(5)67-49(43)71-28/h21-26,28-29,31-45,47-52,55-63H,9-20H2,1-8H3/t21-,22-,23-,24-,25+,26+,28+,29-,31-,32-,33-,34+,35+,36+,37+,38-,39-,40+,41+,42-,43-,44-,45-,47+,48-,49+,50+,51+/m1/s1
SMILES:	CCC[C@H]1CCCCCCCCCC(=O)O[C@H]2[C@H](O[C@H]3[C@H](OC[C@H]4O[C@@H](O[C@H]5[C@H](O1)O[C@H](C)[C@H]([C@@H]5O)O)[C@H](O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)OC(=O)C)[C@H]([C@@H]4O)O)O[C@H](C)[C@H]([C@@H]3O)O)O[C@H]([C@@H]([C@H]2O)OC(=O)[C@@H]([C@H](O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2146618
PubChem CID:	71452845
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

*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
NPO13214	Ipomoea alba	Species	Convolvulaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22924480]
NPO13214	Ipomoea alba	Species	Convolvulaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28006904]
NPO13214	Ipomoea alba	Species	Convolvulaceae	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
IC50	3
Others	3

Activity Type	# Activity
Cell Line	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[493236]
NPT2	Others	Unspecified		FC	=	4.2	n.a.	PMID[493236]
NPT2	Others	Unspecified		FC	=	3.1	n.a.	PMID[493236]
NPT2	Others	Unspecified		FC	=	2.1	n.a.	PMID[493236]

☑ 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 NPC60849 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	673
0.1-0.2	4468
0.2-0.3	12759
0.3-0.4	12290
0.4-0.5	7419
0.5-0.6	3022
0.6-0.7	1393
0.7-0.8	569
0.8-0.85	24
0.85-0.9	8
0.9-0.95	22
0.95-1	50

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472352
1.0	High Similarity	NPC477332
0.974	High Similarity	NPC477317
0.974	High Similarity	NPC44782
0.974	High Similarity	NPC119583
0.974	High Similarity	NPC472205
0.974	High Similarity	NPC224953
0.974	High Similarity	NPC477347
0.974	High Similarity	NPC475270
0.974	High Similarity	NPC472203
0.974	High Similarity	NPC477319
0.974	High Similarity	NPC143421
0.974	High Similarity	NPC238056
0.974	High Similarity	NPC475327
0.974	High Similarity	NPC173328
0.974	High Similarity	NPC472202
0.974	High Similarity	NPC475667
0.974	High Similarity	NPC27289
0.974	High Similarity	NPC297768
0.974	High Similarity	NPC307400
0.974	High Similarity	NPC169345
0.974	High Similarity	NPC115013
0.974	High Similarity	NPC184915
0.974	High Similarity	NPC259294
0.974	High Similarity	NPC472200
0.974	High Similarity	NPC477331
0.974	High Similarity	NPC472204
0.974	High Similarity	NPC290012
0.974	High Similarity	NPC476087
0.974	High Similarity	NPC123204
0.974	High Similarity	NPC477318
0.974	High Similarity	NPC186992
0.974	High Similarity	NPC89843
0.974	High Similarity	NPC472201
0.974	High Similarity	NPC183888
0.974	High Similarity	NPC126685
0.974	High Similarity	NPC269318
0.961	High Similarity	NPC267592
0.9481	High Similarity	NPC85759
0.9481	High Similarity	NPC477346
0.9481	High Similarity	NPC294748
0.9481	High Similarity	NPC146992
0.9481	High Similarity	NPC158302
0.9481	High Similarity	NPC22742
0.9481	High Similarity	NPC477344
0.9351	High Similarity	NPC477329
0.9351	High Similarity	NPC113745
0.9351	High Similarity	NPC281563
0.9351	High Similarity	NPC477325
0.9351	High Similarity	NPC477326
0.9351	High Similarity	NPC109887
0.9351	High Similarity	NPC477328
0.9351	High Similarity	NPC475425
0.9351	High Similarity	NPC477323
0.9351	High Similarity	NPC477320
0.9351	High Similarity	NPC477330
0.9351	High Similarity	NPC146380
0.9091	High Similarity	NPC477350
0.8974	High Similarity	NPC216883
0.8974	High Similarity	NPC476783
0.8974	High Similarity	NPC476781
0.8974	High Similarity	NPC476782
0.8701	High Similarity	NPC225748
0.8701	High Similarity	NPC163812
0.8701	High Similarity	NPC9763
0.8701	High Similarity	NPC39266
0.8701	High Similarity	NPC169085
0.8701	High Similarity	NPC206823
0.8442	Intermediate Similarity	NPC52268
0.8442	Intermediate Similarity	NPC53760
0.8312	Intermediate Similarity	NPC211428
0.8312	Intermediate Similarity	NPC285003
0.8312	Intermediate Similarity	NPC241265
0.8242	Intermediate Similarity	NPC475525
0.8242	Intermediate Similarity	NPC475241
0.8242	Intermediate Similarity	NPC476066
0.8242	Intermediate Similarity	NPC473605
0.8242	Intermediate Similarity	NPC475164
0.8242	Intermediate Similarity	NPC473765
0.8242	Intermediate Similarity	NPC475540
0.8242	Intermediate Similarity	NPC475593
0.8242	Intermediate Similarity	NPC475375
0.8228	Intermediate Similarity	NPC291228
0.8228	Intermediate Similarity	NPC308096
0.8214	Intermediate Similarity	NPC248415
0.8182	Intermediate Similarity	NPC250619
0.8182	Intermediate Similarity	NPC67099
0.8182	Intermediate Similarity	NPC97736
0.8182	Intermediate Similarity	NPC50228
0.8101	Intermediate Similarity	NPC185419
0.8101	Intermediate Similarity	NPC184550
0.8052	Intermediate Similarity	NPC206601
0.8022	Intermediate Similarity	NPC44682
0.8022	Intermediate Similarity	NPC477348
0.8022	Intermediate Similarity	NPC163409
0.8022	Intermediate Similarity	NPC238264
0.8022	Intermediate Similarity	NPC477345
0.7955	Intermediate Similarity	NPC51662
0.7802	Intermediate Similarity	NPC477349
0.7792	Intermediate Similarity	NPC471760
0.7792	Intermediate Similarity	NPC76881
0.7792	Intermediate Similarity	NPC190418
0.7792	Intermediate Similarity	NPC12040
0.7792	Intermediate Similarity	NPC471761
0.77	Intermediate Similarity	NPC22709
0.7662	Intermediate Similarity	NPC6848
0.7653	Intermediate Similarity	NPC469827
0.7653	Intermediate Similarity	NPC470519
0.7653	Intermediate Similarity	NPC231271
0.76	Intermediate Similarity	NPC207693
0.7556	Intermediate Similarity	NPC314364
0.7532	Intermediate Similarity	NPC325773
0.75	Intermediate Similarity	NPC471430
0.7468	Intermediate Similarity	NPC477752
0.7468	Intermediate Similarity	NPC477756
0.7468	Intermediate Similarity	NPC477751
0.7468	Intermediate Similarity	NPC477764
0.7451	Intermediate Similarity	NPC470622
0.7426	Intermediate Similarity	NPC469826
0.7412	Intermediate Similarity	NPC474003
0.74	Intermediate Similarity	NPC273189
0.74	Intermediate Similarity	NPC184805
0.7375	Intermediate Similarity	NPC477754
0.7375	Intermediate Similarity	NPC477761
0.7375	Intermediate Similarity	NPC477759
0.7375	Intermediate Similarity	NPC477758
0.7375	Intermediate Similarity	NPC477760
0.7353	Intermediate Similarity	NPC469825
0.7327	Intermediate Similarity	NPC126753
0.7308	Intermediate Similarity	NPC157571
0.7303	Intermediate Similarity	NPC470313
0.7303	Intermediate Similarity	NPC473500
0.7303	Intermediate Similarity	NPC38295
0.7303	Intermediate Similarity	NPC156089
0.73	Intermediate Similarity	NPC267637
0.7282	Intermediate Similarity	NPC471431
0.7273	Intermediate Similarity	NPC477757
0.7273	Intermediate Similarity	NPC477763
0.7273	Intermediate Similarity	NPC477755
0.7273	Intermediate Similarity	NPC477762
0.7273	Intermediate Similarity	NPC477753
0.7273	Intermediate Similarity	NPC477750
0.7253	Intermediate Similarity	NPC470657
0.7212	Intermediate Similarity	NPC469824
0.7196	Intermediate Similarity	NPC33012
0.7196	Intermediate Similarity	NPC473452
0.7196	Intermediate Similarity	NPC123522
0.7196	Intermediate Similarity	NPC8524
0.7196	Intermediate Similarity	NPC475514
0.7196	Intermediate Similarity	NPC475209
0.7196	Intermediate Similarity	NPC471580
0.7196	Intermediate Similarity	NPC85154
0.7196	Intermediate Similarity	NPC104137
0.7196	Intermediate Similarity	NPC286457
0.7196	Intermediate Similarity	NPC220160
0.7196	Intermediate Similarity	NPC102505
0.7196	Intermediate Similarity	NPC69811
0.7196	Intermediate Similarity	NPC309223
0.7196	Intermediate Similarity	NPC191827
0.7196	Intermediate Similarity	NPC470876
0.7174	Intermediate Similarity	NPC31349
0.717	Intermediate Similarity	NPC477465
0.7157	Intermediate Similarity	NPC287269
0.7143	Intermediate Similarity	NPC312498
0.7143	Intermediate Similarity	NPC473849
0.713	Intermediate Similarity	NPC237191
0.7115	Intermediate Similarity	NPC66513
0.7103	Intermediate Similarity	NPC51465
0.7103	Intermediate Similarity	NPC305267
0.7103	Intermediate Similarity	NPC288205
0.7103	Intermediate Similarity	NPC75287
0.7103	Intermediate Similarity	NPC476992
0.7103	Intermediate Similarity	NPC26626
0.71	Intermediate Similarity	NPC80640
0.71	Intermediate Similarity	NPC80191
0.71	Intermediate Similarity	NPC310031
0.7087	Intermediate Similarity	NPC473688
0.7087	Intermediate Similarity	NPC231566
0.7087	Intermediate Similarity	NPC262567
0.7087	Intermediate Similarity	NPC471626
0.7079	Intermediate Similarity	NPC236649
0.7079	Intermediate Similarity	NPC21693
0.7075	Intermediate Similarity	NPC146563
0.7071	Intermediate Similarity	NPC471428
0.7071	Intermediate Similarity	NPC471427
0.7071	Intermediate Similarity	NPC471426
0.7064	Intermediate Similarity	NPC471577
0.7064	Intermediate Similarity	NPC473386
0.7037	Intermediate Similarity	NPC473824
0.7037	Intermediate Similarity	NPC475119
0.7019	Intermediate Similarity	NPC228190
0.7019	Intermediate Similarity	NPC92297
0.7019	Intermediate Similarity	NPC94086
0.7019	Intermediate Similarity	NPC273002
0.7019	Intermediate Similarity	NPC87393
0.7019	Intermediate Similarity	NPC473817
0.7019	Intermediate Similarity	NPC233433
0.7019	Intermediate Similarity	NPC236753
0.7019	Intermediate Similarity	NPC220836
0.7013	Intermediate Similarity	NPC317023

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 NPC60849 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	730
0.1-0.2	4222
0.2-0.3	2871
0.3-0.4	838
0.4-0.5	317
0.5-0.6	121
0.6-0.7	45
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8072	Intermediate Similarity	NPD7329	Approved
0.7273	Intermediate Similarity	NPD6123	Approved
0.7143	Intermediate Similarity	NPD3181	Approved
0.6951	Remote Similarity	NPD897	Approved
0.6951	Remote Similarity	NPD898	Approved
0.6951	Remote Similarity	NPD896	Approved
0.6931	Remote Similarity	NPD8138	Approved
0.6931	Remote Similarity	NPD8084	Approved
0.6931	Remote Similarity	NPD8083	Approved
0.6931	Remote Similarity	NPD8139	Approved
0.6931	Remote Similarity	NPD8085	Approved
0.6931	Remote Similarity	NPD8082	Approved
0.6931	Remote Similarity	NPD8086	Approved
0.6893	Remote Similarity	NPD8393	Approved
0.6863	Remote Similarity	NPD8275	Approved
0.6863	Remote Similarity	NPD8276	Approved
0.6796	Remote Similarity	NPD8081	Approved
0.6796	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD8133	Approved
0.6729	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8307	Discontinued
0.6667	Remote Similarity	NPD8140	Approved
0.6637	Remote Similarity	NPD8516	Approved
0.6637	Remote Similarity	NPD8517	Approved
0.6637	Remote Similarity	NPD8515	Approved
0.6577	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD8305	Approved
0.6542	Remote Similarity	NPD8306	Approved
0.6542	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3728	Approved
0.6494	Remote Similarity	NPD3730	Approved
0.6494	Remote Similarity	NPD7346	Approved
0.6491	Remote Similarity	NPD8513	Phase 3
0.6481	Remote Similarity	NPD8087	Discontinued
0.6442	Remote Similarity	NPD7140	Approved
0.6442	Remote Similarity	NPD7139	Approved
0.6442	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD7909	Approved
0.6383	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD3669	Approved
0.6379	Remote Similarity	NPD8328	Phase 3
0.6364	Remote Similarity	NPD891	Phase 3
0.6364	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD893	Approved
0.6364	Remote Similarity	NPD888	Phase 3
0.6364	Remote Similarity	NPD892	Phase 3
0.6322	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.63	Remote Similarity	NPD8171	Discontinued
0.6265	Remote Similarity	NPD8961	Approved
0.6261	Remote Similarity	NPD8346	Approved
0.6261	Remote Similarity	NPD8347	Approved
0.6261	Remote Similarity	NPD8345	Approved
0.6234	Remote Similarity	NPD2269	Approved
0.617	Remote Similarity	NPD1780	Approved
0.617	Remote Similarity	NPD1779	Approved
0.6147	Remote Similarity	NPD6686	Approved
0.614	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD8300	Approved
0.6132	Remote Similarity	NPD8301	Approved
0.6104	Remote Similarity	NPD904	Phase 3
0.6104	Remote Similarity	NPD905	Approved
0.6091	Remote Similarity	NPD6941	Approved
0.604	Remote Similarity	NPD7983	Approved
0.6022	Remote Similarity	NPD4238	Approved
0.6022	Remote Similarity	NPD4802	Phase 2
0.5949	Remote Similarity	NPD889	Approved
0.5949	Remote Similarity	NPD895	Approved
0.5949	Remote Similarity	NPD894	Approved
0.5949	Remote Similarity	NPD887	Approved
0.5941	Remote Similarity	NPD6698	Approved
0.5941	Remote Similarity	NPD46	Approved
0.5932	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD2267	Suspended
0.5909	Remote Similarity	NPD6412	Phase 2
0.5882	Remote Similarity	NPD8080	Discontinued
0.5872	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD8959	Approved
0.5833	Remote Similarity	NPD7829	Approved
0.5833	Remote Similarity	NPD7830	Approved
0.5825	Remote Similarity	NPD1446	Phase 3
0.5825	Remote Similarity	NPD1447	Phase 3
0.582	Remote Similarity	NPD8448	Approved
0.5806	Remote Similarity	NPD8390	Approved
0.5806	Remote Similarity	NPD8392	Approved
0.5806	Remote Similarity	NPD8391	Approved
0.5798	Remote Similarity	NPD8444	Approved
0.5785	Remote Similarity	NPD8341	Approved
0.5785	Remote Similarity	NPD8340	Approved
0.5785	Remote Similarity	NPD8299	Approved
0.5785	Remote Similarity	NPD8342	Approved
0.5776	Remote Similarity	NPD6940	Discontinued
0.5761	Remote Similarity	NPD1810	Approved
0.5761	Remote Similarity	NPD1811	Approved
0.5738	Remote Similarity	NPD8451	Approved
0.5732	Remote Similarity	NPD73	Approved
0.5714	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD2255	Approved
0.5679	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD369	Approved
0.566	Remote Similarity	NPD7839	Suspended
0.5607	Remote Similarity	NPD881	Approved
0.56	Remote Similarity	NPD7319	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