NPASS Compound

Structure

CID121453 OpenBabel06191715472D 55 62 0 0 1 0 0 0 0 0999 V2000 10.9752 0.1660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7547 -0.1072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2041 1.3640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7630 -0.7138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0269 0.8578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8773 0.3675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7458 -0.7138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3285 -1.1061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8790 -2.5760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6274 0.8557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3270 1.8382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.2889 -1.5947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4720 0.8490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4235 -1.0532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7630 -2.4756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6608 -0.8014 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 13.2717 -1.5947 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1783 -0.6148 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1777 0.3668 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0286 -1.1051 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4775 0.3659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4781 -0.6157 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4769 2.3280 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6271 1.8367 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.7283 -2.0850 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9811 -0.0004 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0241 -0.1571 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.7283 -1.1044 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4713 -0.8503 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9803 -1.6997 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6489 0.8411 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0008 -1.6993 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2252 1.6350 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0483 -0.0550 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2010 1.5329 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4909 -0.8494 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8779 -0.6141 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3273 0.8571 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.2372 -1.5947 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 14.7975 -0.7138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4531 0.8486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8472 -1.8472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6013 -1.1227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4762 3.3408 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4523 -0.8507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4705 -2.5496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6731 0.9432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4917 -2.5487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8258 2.5311 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7458 -2.4756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7773 2.3269 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 3.6004 0.6368 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4720 -0.8490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6608 -2.3880 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 4 7 1 0 0 0 0 4 17 1 0 0 0 0 5 6 1 0 0 0 0 5 19 1 0 0 0 0 6 37 1 0 0 0 0 8 22 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 10 24 1 0 0 0 0 11 23 1 0 0 0 0 11 38 1 0 0 0 0 12 40 1 0 0 0 0 13 41 1 0 0 0 0 14 42 1 0 0 0 0 15 17 1 0 0 0 0 15 50 1 0 0 0 0 16 28 1 0 0 0 0 16 39 1 6 0 0 0 17 12 1 1 0 0 0 18 8 1 6 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 38 1 1 0 0 0 20 37 1 1 0 0 0 21 22 1 0 0 0 0 21 38 1 1 0 0 0 22 43 1 1 0 0 0 23 24 1 0 0 0 0 23 44 1 6 0 0 0 24 51 1 1 0 0 0 25 9 1 1 0 0 0 25 28 1 0 0 0 0 25 55 1 0 0 0 0 26 13 1 1 0 0 0 26 29 1 0 0 0 0 26 52 1 0 0 0 0 27 14 1 6 0 0 0 27 34 1 0 0 0 0 27 53 1 0 0 0 0 28 37 1 1 0 0 0 29 30 1 0 0 0 0 29 45 1 6 0 0 0 30 32 1 0 0 0 0 30 46 1 1 0 0 0 31 33 1 0 0 0 0 31 34 1 0 0 0 0 31 47 1 6 0 0 0 32 36 1 0 0 0 0 32 48 1 6 0 0 0 33 35 1 0 0 0 0 33 49 1 1 0 0 0 34 54 1 6 0 0 0 35 51 1 6 0 0 0 35 53 1 0 0 0 0 36 52 1 0 0 0 0 36 54 1 1 0 0 0 37 2 1 1 0 0 0 38 3 1 1 0 0 0 39 7 1 1 0 0 0 39 50 1 0 0 0 0 39 55 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	788.42
Volume:	755.292
LogP:	-0.234
LogD:	0.747
LogS:	-2.72
# Rotatable Bonds:	7
TPSA:	257.68
# H-Bond Aceptor:	16
# H-Bond Donor:	10
# Rings:	8
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.13
Synthetic Accessibility Score:	6.523
Fsp3:	1.0
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:	-6.487
MDCK Permeability:	0.00025136140175163746
Pgp-inhibitor:	0.009
Pgp-substrate:	0.938
Human Intestinal Absorption (HIA):	0.985
20% Bioavailability (F20%):	0.955
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	32.62085723876953%
Volume Distribution (VD):	0.135
Pgp-substrate:	25.52357292175293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.013

ADMET: Excretion

Clearance (CL):	0.773
Half-life (T1/2):	0.74

ADMET: Toxicity

hERG Blockers:	0.826
Human Hepatotoxicity (H-HT):	0.207
Drug-inuced Liver Injury (DILI):	0.151
AMES Toxicity:	0.101
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.947
Carcinogencity:	0.189
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC121453

Natural Product ID:	NPC121453
*Common Name:**	Atroviolaceoside
IUPAC Name:	n.a.
Synonyms:	Atroviolaceoside
Standard InCHIKey:	UPXMNFSCVVTVFO-IZISHBDUSA-N
Standard InCHI:	InChI=1S/C39H64O16/c1-16-28-25(55-39(16)7-4-17(12-40)15-50-39)9-20-18-8-22(43)21-10-24(23(44)11-38(21,3)19(18)5-6-37(20,28)2)51-35-33(49)31(47)34(27(14-42)53-35)54-36-32(48)30(46)29(45)26(13-41)52-36/h16-36,40-49H,4-15H2,1-3H3/t16-,17-,18+,19-,20-,21+,22+,23+,24+,25-,26+,27+,28-,29+,30-,31+,32+,33+,34-,35+,36-,37-,38+,39+/m0/s1
SMILES:	C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4C[C@H]([C@H]5C[C@H]([C@@H](C[C@]5(C)[C@H]4CC[C@]23C)O)O[C@H]2[C@@H]([C@H]([C@H]([C@@H](CO)O2)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O)O)O)O[C@@]21CC[C@@H](CO)CO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449185
PubChem CID:	11614761
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

*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
NPO4610	Allium atroviolaceum	Species	Amaryllidaceae	Eukaryota	bulbs and flowers	Semirum (2300 m), Isfhan Provinces, Iran	2002-JUN, 2003	PMID[16499315]
NPO6165	Prunus salicina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28202328]
NPO6165	Prunus salicina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6165	Prunus salicina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6165	Prunus salicina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6165	Prunus salicina	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8088	Tanacetum densum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8221	Cladonia crispata	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4610	Allium atroviolaceum	Species	Amaryllidaceae	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
Others	1

Activity Type	# Activity
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT548	Tissue	Ileum	Cavia porcellus	Inhibition	=	0.0	%	PMID[510353]

☑ 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 NPC121453 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	600
0.1-0.2	5233
0.2-0.3	14084
0.3-0.4	10419
0.4-0.5	5525
0.5-0.6	3481
0.6-0.7	1863
0.7-0.8	983
0.8-0.85	245
0.85-0.9	115
0.9-0.95	49
0.95-1	100

Similarity Score	Similarity Level	Natural Product ID
0.978	High Similarity	NPC473518
0.9778	High Similarity	NPC195297
0.9778	High Similarity	NPC139271
0.9778	High Similarity	NPC304011
0.9778	High Similarity	NPC473601
0.9775	High Similarity	NPC291547
0.9775	High Similarity	NPC174024
0.9775	High Similarity	NPC217205
0.9775	High Similarity	NPC179859
0.9775	High Similarity	NPC291203
0.9775	High Similarity	NPC253268
0.9775	High Similarity	NPC475436
0.9775	High Similarity	NPC131693
0.9775	High Similarity	NPC222731
0.9775	High Similarity	NPC312678
0.9775	High Similarity	NPC294686
0.9775	High Similarity	NPC473851
0.967	High Similarity	NPC303069
0.967	High Similarity	NPC83137
0.967	High Similarity	NPC232611
0.967	High Similarity	NPC51520
0.967	High Similarity	NPC477223
0.967	High Similarity	NPC115165
0.967	High Similarity	NPC307534
0.967	High Similarity	NPC470861
0.967	High Similarity	NPC477222
0.967	High Similarity	NPC470862
0.967	High Similarity	NPC476112
0.9667	High Similarity	NPC19400
0.9667	High Similarity	NPC475351
0.9667	High Similarity	NPC107188
0.9667	High Similarity	NPC6295
0.9667	High Similarity	NPC473727
0.9667	High Similarity	NPC211354
0.9667	High Similarity	NPC206003
0.9667	High Similarity	NPC473610
0.9667	High Similarity	NPC107962
0.9663	High Similarity	NPC297348
0.9663	High Similarity	NPC149400
0.9663	High Similarity	NPC249204
0.9663	High Similarity	NPC88962
0.9663	High Similarity	NPC172838
0.9663	High Similarity	NPC477451
0.9663	High Similarity	NPC234352
0.9663	High Similarity	NPC177834
0.9663	High Similarity	NPC477547
0.9663	High Similarity	NPC141769
0.9663	High Similarity	NPC137004
0.9663	High Similarity	NPC325828
0.9663	High Similarity	NPC144790
0.9663	High Similarity	NPC250393
0.9663	High Similarity	NPC48339
0.9565	High Similarity	NPC291548
0.956	High Similarity	NPC128572
0.956	High Similarity	NPC98018
0.956	High Similarity	NPC470864
0.956	High Similarity	NPC30856
0.956	High Similarity	NPC116756
0.956	High Similarity	NPC184617
0.956	High Similarity	NPC132080
0.956	High Similarity	NPC103616
0.956	High Similarity	NPC287483
0.956	High Similarity	NPC470863
0.956	High Similarity	NPC475643
0.956	High Similarity	NPC232037
0.956	High Similarity	NPC84111
0.956	High Similarity	NPC97700
0.956	High Similarity	NPC475625
0.956	High Similarity	NPC284104
0.956	High Similarity	NPC470865
0.956	High Similarity	NPC470866
0.956	High Similarity	NPC160426
0.9556	High Similarity	NPC45959
0.9556	High Similarity	NPC252253
0.9556	High Similarity	NPC471464
0.9556	High Similarity	NPC264101
0.9556	High Similarity	NPC473774
0.9556	High Similarity	NPC305418
0.9556	High Similarity	NPC24960
0.9551	High Similarity	NPC5632
0.9551	High Similarity	NPC149966
0.9457	High Similarity	NPC274200
0.9451	High Similarity	NPC474399
0.9438	High Similarity	NPC473542
0.9438	High Similarity	NPC65550
0.9348	High Similarity	NPC142264
0.9348	High Similarity	NPC476510
0.9341	High Similarity	NPC477224
0.9341	High Similarity	NPC3538
0.9341	High Similarity	NPC113500
0.9333	High Similarity	NPC307167
0.9333	High Similarity	NPC229801
0.9333	High Similarity	NPC204881
0.9333	High Similarity	NPC210759
0.9333	High Similarity	NPC473830
0.9326	High Similarity	NPC20822
0.9326	High Similarity	NPC473472
0.9247	High Similarity	NPC475207
0.9247	High Similarity	NPC470028
0.9247	High Similarity	NPC470591
0.9247	High Similarity	NPC233649
0.9239	High Similarity	NPC92196
0.9231	High Similarity	NPC473726
0.9231	High Similarity	NPC167644
0.9231	High Similarity	NPC311246
0.9222	High Similarity	NPC223143
0.9213	High Similarity	NPC281004
0.9158	High Similarity	NPC475574
0.9149	High Similarity	NPC473616
0.9149	High Similarity	NPC473638
0.913	High Similarity	NPC309866
0.913	High Similarity	NPC175
0.9121	High Similarity	NPC293609
0.9111	High Similarity	NPC82955
0.9111	High Similarity	NPC102725
0.9111	High Similarity	NPC131466
0.9043	High Similarity	NPC210157
0.9032	High Similarity	NPC473067
0.9032	High Similarity	NPC477494
0.9032	High Similarity	NPC473064
0.9032	High Similarity	NPC473065
0.9022	High Similarity	NPC476669
0.9022	High Similarity	NPC277774
0.9011	High Similarity	NPC279329
0.8958	High Similarity	NPC476512
0.8958	High Similarity	NPC472081
0.8958	High Similarity	NPC108227
0.8958	High Similarity	NPC477225
0.8936	High Similarity	NPC237071
0.8936	High Similarity	NPC203434
0.8936	High Similarity	NPC238796
0.8936	High Similarity	NPC296936
0.8925	High Similarity	NPC475325
0.8913	High Similarity	NPC36372
0.8913	High Similarity	NPC473637
0.8913	High Similarity	NPC476668
0.8889	High Similarity	NPC140446
0.8889	High Similarity	NPC43912
0.8876	High Similarity	NPC273290
0.8876	High Similarity	NPC232044
0.8866	High Similarity	NPC134967
0.8866	High Similarity	NPC310138
0.8866	High Similarity	NPC114700
0.8866	High Similarity	NPC470029
0.883	High Similarity	NPC94582
0.883	High Similarity	NPC57964
0.8817	High Similarity	NPC18724
0.8817	High Similarity	NPC470623
0.8817	High Similarity	NPC323231
0.8817	High Similarity	NPC171741
0.8817	High Similarity	NPC224003
0.8776	High Similarity	NPC97260
0.8776	High Similarity	NPC139181
0.8776	High Similarity	NPC476837
0.8764	High Similarity	NPC227260
0.8763	High Similarity	NPC476839
0.8763	High Similarity	NPC476838
0.8737	High Similarity	NPC473287
0.8723	High Similarity	NPC473503
0.8723	High Similarity	NPC30687
0.8723	High Similarity	NPC267238
0.8723	High Similarity	NPC77717
0.8723	High Similarity	NPC471373
0.8723	High Similarity	NPC253611
0.8723	High Similarity	NPC148593
0.8713	High Similarity	NPC151134
0.871	High Similarity	NPC59006
0.87	High Similarity	NPC54619
0.8673	High Similarity	NPC310031
0.8673	High Similarity	NPC80191
0.8667	High Similarity	NPC290612
0.8632	High Similarity	NPC471429
0.8632	High Similarity	NPC471424
0.8632	High Similarity	NPC205129
0.8632	High Similarity	NPC106701
0.8632	High Similarity	NPC189575
0.8632	High Similarity	NPC469710
0.8632	High Similarity	NPC471425
0.8627	High Similarity	NPC470867
0.8614	High Similarity	NPC49032
0.8614	High Similarity	NPC202898
0.8614	High Similarity	NPC51172
0.8614	High Similarity	NPC125324
0.8614	High Similarity	NPC92890
0.8614	High Similarity	NPC475319
0.86	High Similarity	NPC215408
0.8587	High Similarity	NPC128475
0.8571	High Similarity	NPC471240
0.8539	High Similarity	NPC296734
0.8539	High Similarity	NPC470611
0.8529	High Similarity	NPC233433
0.8529	High Similarity	NPC92297
0.8529	High Similarity	NPC220836
0.8529	High Similarity	NPC473817
0.8529	High Similarity	NPC94086
0.8529	High Similarity	NPC273002
0.85	High Similarity	NPC475521
0.8495	Intermediate Similarity	NPC228059
0.8478	Intermediate Similarity	NPC210658
0.8478	Intermediate Similarity	NPC161928

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 NPC121453 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	572
0.1-0.2	4700
0.2-0.3	2750
0.3-0.4	598
0.4-0.5	321
0.5-0.6	161
0.6-0.7	30
0.7-0.8	15
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9663	High Similarity	NPD8171	Discontinued
0.8687	High Similarity	NPD8170	Clinical (unspecified phase)
0.8315	Intermediate Similarity	NPD6928	Phase 2
0.7611	Intermediate Similarity	NPD8377	Approved
0.7611	Intermediate Similarity	NPD8294	Approved
0.7545	Intermediate Similarity	NPD8133	Approved
0.7544	Intermediate Similarity	NPD8296	Approved
0.7544	Intermediate Similarity	NPD8380	Approved
0.7544	Intermediate Similarity	NPD8335	Approved
0.7544	Intermediate Similarity	NPD8379	Approved
0.7544	Intermediate Similarity	NPD8378	Approved
0.7391	Intermediate Similarity	NPD8033	Approved
0.7353	Intermediate Similarity	NPD7991	Discontinued
0.7217	Intermediate Similarity	NPD7516	Approved
0.713	Intermediate Similarity	NPD7328	Approved
0.713	Intermediate Similarity	NPD7327	Approved
0.7	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD1810	Approved
0.6882	Remote Similarity	NPD1811	Approved
0.6875	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD8450	Suspended
0.6721	Remote Similarity	NPD7507	Approved
0.6696	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD8449	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.661	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7319	Approved
0.6559	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD2686	Approved
0.6559	Remote Similarity	NPD2687	Approved
0.6559	Remote Similarity	NPD2254	Approved
0.6525	Remote Similarity	NPD6940	Discontinued
0.6491	Remote Similarity	NPD8174	Phase 2
0.648	Remote Similarity	NPD7736	Approved
0.6436	Remote Similarity	NPD3669	Approved
0.6436	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6115	Approved
0.6429	Remote Similarity	NPD6697	Approved
0.6429	Remote Similarity	NPD6114	Approved
0.6429	Remote Similarity	NPD6118	Approved
0.6423	Remote Similarity	NPD8328	Phase 3
0.6383	Remote Similarity	NPD4787	Phase 1
0.6341	Remote Similarity	NPD6370	Approved
0.6327	Remote Similarity	NPD6116	Phase 1
0.627	Remote Similarity	NPD8293	Discontinued
0.6264	Remote Similarity	NPD371	Approved
0.6224	Remote Similarity	NPD6117	Approved
0.6179	Remote Similarity	NPD6059	Approved
0.6179	Remote Similarity	NPD6054	Approved
0.6111	Remote Similarity	NPD6123	Approved
0.6043	Remote Similarity	NPD7625	Phase 1
0.6032	Remote Similarity	NPD6067	Discontinued
0.602	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD6016	Approved
0.5984	Remote Similarity	NPD7492	Approved
0.598	Remote Similarity	NPD7525	Registered
0.5979	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD1700	Approved
0.5963	Remote Similarity	NPD8034	Phase 2
0.5963	Remote Similarity	NPD8035	Phase 2
0.596	Remote Similarity	NPD3703	Phase 2
0.5952	Remote Similarity	NPD5988	Approved
0.5938	Remote Similarity	NPD6616	Approved
0.5932	Remote Similarity	NPD6686	Approved
0.5891	Remote Similarity	NPD7078	Approved
0.5876	Remote Similarity	NPD4245	Approved
0.5876	Remote Similarity	NPD4244	Approved
0.5812	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.58	Remote Similarity	NPD3702	Approved
0.5789	Remote Similarity	NPD7638	Approved
0.5773	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD3698	Phase 2
0.5773	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD1779	Approved
0.5769	Remote Similarity	NPD1780	Approved
0.5748	Remote Similarity	NPD8513	Phase 3
0.5748	Remote Similarity	NPD8515	Approved
0.5748	Remote Similarity	NPD8516	Approved
0.5748	Remote Similarity	NPD8517	Approved
0.5741	Remote Similarity	NPD7524	Approved
0.5739	Remote Similarity	NPD7639	Approved
0.5739	Remote Similarity	NPD7640	Approved
0.5738	Remote Similarity	NPD6882	Approved
0.5738	Remote Similarity	NPD8297	Approved
0.5728	Remote Similarity	NPD7645	Phase 2
0.5725	Remote Similarity	NPD6033	Approved
0.5701	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.568	Remote Similarity	NPD6009	Approved
0.5669	Remote Similarity	NPD6319	Approved
0.5667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD2267	Suspended
0.5657	Remote Similarity	NPD5777	Approved
0.5648	Remote Similarity	NPD8308	Discontinued
0.5641	Remote Similarity	NPD7632	Discontinued
0.5618	Remote Similarity	NPD7346	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