NPASS Compound

Structure

NPC102619 OpenBabel07101718322D 49 54 0 0 1 0 0 0 0 0999 V2000 -0.2874 3.4495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5511 4.5874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4302 -2.2456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3640 -1.9422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8503 -1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8503 -0.4909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3012 0.8969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1618 2.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8503 -1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7006 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5508 0.4909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8811 3.0266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9377 1.2372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0841 -3.6010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2477 3.6536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9047 2.9240 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8503 1.4727 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8503 1.4727 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4835 -2.7041 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7006 -0.9818 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2805 2.1297 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6343 0.3034 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8981 1.4413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7006 1.9636 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4599 -2.6014 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8592 -1.7045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2821 -0.9102 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8503 0.4909 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3057 -1.0128 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1279 0.6784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6343 -1.2852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8503 0.4909 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7006 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5508 1.4727 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6612 -4.3953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7006 1.9636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2408 1.9256 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5550 0.7117 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0370 -3.3957 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8357 -1.6019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6815 -0.0133 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1044 0.7810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2015 2.3751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9064 -1.9098 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7286 -0.2185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2114 -0.4909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 17 1 0 0 0 0 3 33 1 0 0 0 0 4 33 1 0 0 0 0 5 34 1 0 0 0 0 8 46 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 35 1 0 0 0 0 11 12 1 0 0 0 0 11 34 1 0 0 0 0 12 37 1 0 0 0 0 13 18 1 0 0 0 0 13 23 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 24 1 0 0 0 0 15 25 1 0 0 0 0 16 38 1 0 0 0 0 18 17 1 1 0 0 0 18 26 1 0 0 0 0 19 26 1 0 0 0 0 19 34 1 1 0 0 0 20 30 1 0 0 0 0 20 39 1 1 0 0 0 21 16 1 6 0 0 0 21 27 1 0 0 0 0 21 47 1 0 0 0 0 22 33 1 0 0 0 0 22 36 1 6 0 0 0 23 37 1 1 0 0 0 23 40 1 0 0 0 0 24 36 1 1 0 0 0 24 49 1 0 0 0 0 25 41 2 0 0 0 0 25 46 1 0 0 0 0 26 37 1 6 0 0 0 27 28 1 0 0 0 0 27 42 1 1 0 0 0 28 29 1 0 0 0 0 28 43 1 6 0 0 0 29 31 1 0 0 0 0 29 44 1 1 0 0 0 30 35 1 6 0 0 0 30 36 1 0 0 0 0 31 47 1 0 0 0 0 31 48 1 6 0 0 0 32 45 2 0 0 0 0 32 48 1 0 0 0 0 33 49 1 0 0 0 0 34 35 1 6 0 0 0 35 6 1 6 0 0 0 36 7 1 6 0 0 0 37 32 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	694.39
Volume:	694.743
LogP:	2.397
LogD:	2.68
LogS:	-3.436
# Rotatable Bonds:	8
TPSA:	192.44
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.175
Synthetic Accessibility Score:	5.953
Fsp3:	0.892
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:	-5.417
MDCK Permeability:	6.55120747978799e-05
Pgp-inhibitor:	0.949
Pgp-substrate:	0.684
Human Intestinal Absorption (HIA):	0.214
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.854

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	66.03225708007812%
Volume Distribution (VD):	0.603
Pgp-substrate:	16.228702545166016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.319
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.73
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.232
CYP3A4-substrate:	0.147

ADMET: Excretion

Clearance (CL):	1.818
Half-life (T1/2):	0.56

ADMET: Toxicity

hERG Blockers:	0.361
Human Hepatotoxicity (H-HT):	0.402
Drug-inuced Liver Injury (DILI):	0.05
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.102
Maximum Recommended Daily Dose:	0.293
Skin Sensitization:	0.182
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.864

Download Data

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

Natural Product: NPC102619

Natural Product ID:	NPC102619
*Common Name:**	Acanthosessilioside C
IUPAC Name:	n.a.
Synonyms:	Acanthosessilioside C
Standard InCHIKey:	PJRCJHUXBYLHNU-RWKILBRVSA-N
Standard InCHI:	InChI=1S/C37H58O12/c1-17(2)18-13-23(40)37(32(45)48-31-29(44)28(43)27(42)21(16-38)47-31)12-11-34(5)19(26(18)37)14-20(39)30-35(34,6)10-9-22-33(3,4)49-24(36(22,30)7)15-25(41)46-8/h18-24,26-31,38-40,42-44H,1,9-16H2,2-8H3/t18-,19+,20+,21+,22-,23-,24+,26+,27+,28-,29+,30-,31-,34+,35+,36+,37+/m0/s1
SMILES:	C=C(C)[C@@H]1C[C@@H]([C@@]2(CC[C@]3(C)[C@H](C[C@H]([C@H]4[C@@]3(C)CC[C@H]3C(C)(C)O[C@H](CC(=O)OC)[C@]43C)O)[C@@H]12)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2063158
PubChem CID:	60155053
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene 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
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	Fruits	n.a.	n.a.	PMID[22691179]
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	<	10000.0	nM	PMID[492833]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	<	10000.0	nM	PMID[492833]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	<	10000.0	nM	PMID[492833]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	<	10000.0	nM	PMID[492833]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	<	10000.0	nM	PMID[492833]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	<	10000.0	nM	PMID[492833]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	IC50	<	10000.0	nM	PMID[492833]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[492833]

☑ 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 NPC102619 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	295
0.1-0.2	2111
0.2-0.3	6684
0.3-0.4	12960
0.4-0.5	7961
0.5-0.6	5583
0.6-0.7	3792
0.7-0.8	2565
0.8-0.85	644
0.85-0.9	93
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9808	High Similarity	NPC272242
0.9712	High Similarity	NPC106760
0.9528	High Similarity	NPC243572
0.9519	High Similarity	NPC224414
0.9252	High Similarity	NPC11035
0.9182	High Similarity	NPC156651
0.9167	High Similarity	NPC470543
0.9151	High Similarity	NPC88744
0.9083	High Similarity	NPC146563
0.9083	High Similarity	NPC73986
0.9065	High Similarity	NPC91583
0.9065	High Similarity	NPC240125
0.9065	High Similarity	NPC473844
0.9065	High Similarity	NPC51947
0.9038	High Similarity	NPC94919
0.9	High Similarity	NPC54395
0.8919	High Similarity	NPC469823
0.8919	High Similarity	NPC469820
0.8919	High Similarity	NPC137414
0.8899	High Similarity	NPC240734
0.8899	High Similarity	NPC1876
0.8899	High Similarity	NPC204392
0.8899	High Similarity	NPC91838
0.8899	High Similarity	NPC275668
0.8889	High Similarity	NPC8431
0.8879	High Similarity	NPC273962
0.8846	High Similarity	NPC108371
0.8807	High Similarity	NPC101450
0.8761	High Similarity	NPC239293
0.8761	High Similarity	NPC469822
0.8727	High Similarity	NPC285410
0.8727	High Similarity	NPC263827
0.8727	High Similarity	NPC274833
0.8727	High Similarity	NPC470311
0.8727	High Similarity	NPC250481
0.8727	High Similarity	NPC471251
0.8718	High Similarity	NPC174367
0.8718	High Similarity	NPC47113
0.8716	High Similarity	NPC471250
0.8704	High Similarity	NPC287269
0.8673	High Similarity	NPC473304
0.8661	High Similarity	NPC477580
0.8661	High Similarity	NPC469821
0.8661	High Similarity	NPC116024
0.8654	High Similarity	NPC253586
0.8649	High Similarity	NPC207845
0.8649	High Similarity	NPC472719
0.8644	High Similarity	NPC471357
0.8644	High Similarity	NPC146456
0.8644	High Similarity	NPC469757
0.8644	High Similarity	NPC117702
0.8636	High Similarity	NPC129340
0.8624	High Similarity	NPC195708
0.8611	High Similarity	NPC285927
0.8611	High Similarity	NPC473199
0.8609	High Similarity	NPC471406
0.8584	High Similarity	NPC88945
0.8571	High Similarity	NPC144068
0.8571	High Similarity	NPC260665
0.8559	High Similarity	NPC31839
0.8558	High Similarity	NPC472989
0.8547	High Similarity	NPC27363
0.8545	High Similarity	NPC477069
0.8545	High Similarity	NPC473570
0.8545	High Similarity	NPC477070
0.8545	High Similarity	NPC265655
0.8545	High Similarity	NPC218853
0.8534	High Similarity	NPC470478
0.8522	High Similarity	NPC477071
0.85	High Similarity	NPC469752
0.85	High Similarity	NPC469753
0.85	High Similarity	NPC471361
0.85	High Similarity	NPC197707
0.85	High Similarity	NPC471358
0.85	High Similarity	NPC219085
0.85	High Similarity	NPC70542
0.85	High Similarity	NPC17896
0.85	High Similarity	NPC471359
0.85	High Similarity	NPC86159
0.85	High Similarity	NPC469751
0.85	High Similarity	NPC10823
0.85	High Similarity	NPC89514
0.85	High Similarity	NPC6108
0.85	High Similarity	NPC180079
0.85	High Similarity	NPC471352
0.85	High Similarity	NPC251866
0.85	High Similarity	NPC9499
0.85	High Similarity	NPC469754
0.85	High Similarity	NPC284406
0.85	High Similarity	NPC471360
0.85	High Similarity	NPC469755
0.8496	Intermediate Similarity	NPC473882
0.8487	Intermediate Similarity	NPC329784
0.8487	Intermediate Similarity	NPC240070
0.8482	Intermediate Similarity	NPC48249
0.8482	Intermediate Similarity	NPC80843
0.8482	Intermediate Similarity	NPC1046
0.8482	Intermediate Similarity	NPC471245
0.8482	Intermediate Similarity	NPC233003
0.8468	Intermediate Similarity	NPC27551
0.8468	Intermediate Similarity	NPC255655
0.8468	Intermediate Similarity	NPC475317
0.8468	Intermediate Similarity	NPC114961
0.8468	Intermediate Similarity	NPC154856
0.8468	Intermediate Similarity	NPC98633
0.8468	Intermediate Similarity	NPC52241
0.8468	Intermediate Similarity	NPC242611
0.8468	Intermediate Similarity	NPC124053
0.8462	Intermediate Similarity	NPC215570
0.8462	Intermediate Similarity	NPC156789
0.8455	Intermediate Similarity	NPC230888
0.8455	Intermediate Similarity	NPC473517
0.8455	Intermediate Similarity	NPC38217
0.8455	Intermediate Similarity	NPC472988
0.8455	Intermediate Similarity	NPC258323
0.8455	Intermediate Similarity	NPC295389
0.8448	Intermediate Similarity	NPC142151
0.8448	Intermediate Similarity	NPC470312
0.8448	Intermediate Similarity	NPC144644
0.8448	Intermediate Similarity	NPC153673
0.8448	Intermediate Similarity	NPC108072
0.8448	Intermediate Similarity	NPC473645
0.8448	Intermediate Similarity	NPC281840
0.8448	Intermediate Similarity	NPC37860
0.8448	Intermediate Similarity	NPC110385
0.8448	Intermediate Similarity	NPC267694
0.8443	Intermediate Similarity	NPC469749
0.8443	Intermediate Similarity	NPC247190
0.8443	Intermediate Similarity	NPC32793
0.8443	Intermediate Similarity	NPC116075
0.8443	Intermediate Similarity	NPC146857
0.844	Intermediate Similarity	NPC165405
0.8435	Intermediate Similarity	NPC475632
0.8435	Intermediate Similarity	NPC86020
0.8435	Intermediate Similarity	NPC232237
0.8435	Intermediate Similarity	NPC105800
0.8426	Intermediate Similarity	NPC213190
0.8421	Intermediate Similarity	NPC472718
0.8421	Intermediate Similarity	NPC244127
0.8417	Intermediate Similarity	NPC311534
0.8411	Intermediate Similarity	NPC31346
0.8411	Intermediate Similarity	NPC477172
0.8407	Intermediate Similarity	NPC178981
0.8407	Intermediate Similarity	NPC238935
0.8407	Intermediate Similarity	NPC132668
0.8407	Intermediate Similarity	NPC251309
0.8407	Intermediate Similarity	NPC471252
0.8407	Intermediate Similarity	NPC285086
0.8407	Intermediate Similarity	NPC477944
0.8407	Intermediate Similarity	NPC475208
0.8403	Intermediate Similarity	NPC250556
0.8403	Intermediate Similarity	NPC469750
0.8396	Intermediate Similarity	NPC157739
0.8393	Intermediate Similarity	NPC292196
0.8393	Intermediate Similarity	NPC114188
0.8393	Intermediate Similarity	NPC473062
0.8393	Intermediate Similarity	NPC122339
0.8393	Intermediate Similarity	NPC329953
0.8393	Intermediate Similarity	NPC270586
0.8393	Intermediate Similarity	NPC477073
0.8393	Intermediate Similarity	NPC469824
0.839	Intermediate Similarity	NPC160084
0.839	Intermediate Similarity	NPC256983
0.839	Intermediate Similarity	NPC41129
0.8378	Intermediate Similarity	NPC57362
0.8378	Intermediate Similarity	NPC131903
0.8378	Intermediate Similarity	NPC296761
0.8378	Intermediate Similarity	NPC154085
0.8378	Intermediate Similarity	NPC306746
0.8378	Intermediate Similarity	NPC167383
0.8378	Intermediate Similarity	NPC51925
0.8378	Intermediate Similarity	NPC43976
0.8378	Intermediate Similarity	NPC204407
0.8378	Intermediate Similarity	NPC125361
0.8378	Intermediate Similarity	NPC237503
0.8378	Intermediate Similarity	NPC137917
0.8376	Intermediate Similarity	NPC293031
0.8376	Intermediate Similarity	NPC68767
0.8376	Intermediate Similarity	NPC475182
0.8376	Intermediate Similarity	NPC275225
0.8376	Intermediate Similarity	NPC51099
0.8374	Intermediate Similarity	NPC329636
0.8364	Intermediate Similarity	NPC470170
0.8364	Intermediate Similarity	NPC234160
0.8364	Intermediate Similarity	NPC470169
0.8362	Intermediate Similarity	NPC207738
0.8349	Intermediate Similarity	NPC475521
0.8349	Intermediate Similarity	NPC475365
0.8349	Intermediate Similarity	NPC85593
0.8349	Intermediate Similarity	NPC469827
0.8349	Intermediate Similarity	NPC31430
0.8348	Intermediate Similarity	NPC93883
0.8348	Intermediate Similarity	NPC179429
0.8347	Intermediate Similarity	NPC188234
0.8347	Intermediate Similarity	NPC477235
0.8347	Intermediate Similarity	NPC276838
0.8347	Intermediate Similarity	NPC232785
0.8347	Intermediate Similarity	NPC329986
0.8347	Intermediate Similarity	NPC125077
0.8347	Intermediate Similarity	NPC140092

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 NPC102619 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	2499
0.2-0.3	3986
0.3-0.4	1518
0.4-0.5	401
0.5-0.6	258
0.6-0.7	151
0.7-0.8	37
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8739	High Similarity	NPD8133	Approved
0.85	High Similarity	NPD7319	Approved
0.8417	Intermediate Similarity	NPD7736	Approved
0.8403	Intermediate Similarity	NPD7507	Approved
0.8182	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD8293	Discontinued
0.8136	Intermediate Similarity	NPD8377	Approved
0.8136	Intermediate Similarity	NPD8294	Approved
0.812	Intermediate Similarity	NPD7327	Approved
0.812	Intermediate Similarity	NPD7328	Approved
0.8067	Intermediate Similarity	NPD8380	Approved
0.8067	Intermediate Similarity	NPD8378	Approved
0.8067	Intermediate Similarity	NPD8296	Approved
0.8067	Intermediate Similarity	NPD8379	Approved
0.8067	Intermediate Similarity	NPD8335	Approved
0.8067	Intermediate Similarity	NPD8033	Approved
0.8051	Intermediate Similarity	NPD7516	Approved
0.8036	Intermediate Similarity	NPD6412	Phase 2
0.8	Intermediate Similarity	NPD6370	Approved
0.7895	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD7492	Approved
0.7833	Intermediate Similarity	NPD6059	Approved
0.7833	Intermediate Similarity	NPD6054	Approved
0.7805	Intermediate Similarity	NPD6616	Approved
0.7787	Intermediate Similarity	NPD8328	Phase 3
0.7757	Intermediate Similarity	NPD8171	Discontinued
0.7742	Intermediate Similarity	NPD7078	Approved
0.7664	Intermediate Similarity	NPD8034	Phase 2
0.7664	Intermediate Similarity	NPD8035	Phase 2
0.7623	Intermediate Similarity	NPD6016	Approved
0.7623	Intermediate Similarity	NPD6015	Approved
0.7561	Intermediate Similarity	NPD5988	Approved
0.7541	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD6686	Approved
0.748	Intermediate Similarity	NPD7503	Approved
0.7429	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD6882	Approved
0.7395	Intermediate Similarity	NPD8297	Approved
0.7295	Intermediate Similarity	NPD6009	Approved
0.7266	Intermediate Similarity	NPD6033	Approved
0.7222	Intermediate Similarity	NPD6067	Discontinued
0.7203	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7320	Approved
0.72	Intermediate Similarity	NPD8513	Phase 3
0.72	Intermediate Similarity	NPD8517	Approved
0.72	Intermediate Similarity	NPD8516	Approved
0.72	Intermediate Similarity	NPD8515	Approved
0.719	Intermediate Similarity	NPD4632	Approved
0.7179	Intermediate Similarity	NPD6675	Approved
0.7179	Intermediate Similarity	NPD6402	Approved
0.7179	Intermediate Similarity	NPD7128	Approved
0.7179	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6373	Approved
0.7143	Intermediate Similarity	NPD6372	Approved
0.7115	Intermediate Similarity	NPD6928	Phase 2
0.7105	Intermediate Similarity	NPD7638	Approved
0.7059	Intermediate Similarity	NPD6899	Approved
0.7059	Intermediate Similarity	NPD6881	Approved
0.7043	Intermediate Similarity	NPD7639	Approved
0.7043	Intermediate Similarity	NPD7640	Approved
0.7034	Intermediate Similarity	NPD6008	Approved
0.7025	Intermediate Similarity	NPD6650	Approved
0.7025	Intermediate Similarity	NPD6649	Approved
0.7025	Intermediate Similarity	NPD8130	Phase 1
0.7016	Intermediate Similarity	NPD7115	Discovery
0.6975	Remote Similarity	NPD5701	Approved
0.6975	Remote Similarity	NPD5697	Approved
0.6942	Remote Similarity	NPD7290	Approved
0.6942	Remote Similarity	NPD7102	Approved
0.6942	Remote Similarity	NPD4634	Approved
0.6942	Remote Similarity	NPD6883	Approved
0.6935	Remote Similarity	NPD6940	Discontinued
0.6923	Remote Similarity	NPD6697	Approved
0.6923	Remote Similarity	NPD6118	Approved
0.6923	Remote Similarity	NPD6115	Approved
0.6923	Remote Similarity	NPD6114	Approved
0.6885	Remote Similarity	NPD6869	Approved
0.6885	Remote Similarity	NPD6847	Approved
0.6885	Remote Similarity	NPD6617	Approved
0.687	Remote Similarity	NPD6083	Phase 2
0.687	Remote Similarity	NPD6084	Phase 2
0.686	Remote Similarity	NPD6012	Approved
0.686	Remote Similarity	NPD6014	Approved
0.686	Remote Similarity	NPD6013	Approved
0.6827	Remote Similarity	NPD6116	Phase 1
0.6822	Remote Similarity	NPD7604	Phase 2
0.6814	Remote Similarity	NPD6399	Phase 3
0.6797	Remote Similarity	NPD5983	Phase 2
0.6777	Remote Similarity	NPD6011	Approved
0.6767	Remote Similarity	NPD5956	Approved
0.6759	Remote Similarity	NPD4788	Approved
0.6754	Remote Similarity	NPD7748	Approved
0.6748	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6117	Approved
0.6724	Remote Similarity	NPD7902	Approved
0.6724	Remote Similarity	NPD4755	Approved
0.6721	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6336	Discontinued
0.6696	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD1700	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6921	Approved
0.6639	Remote Similarity	NPD7632	Discontinued
0.6613	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5286	Approved
0.661	Remote Similarity	NPD4696	Approved
0.661	Remote Similarity	NPD5285	Approved
0.661	Remote Similarity	NPD4700	Approved
0.6607	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7515	Phase 2
0.6557	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5695	Phase 3
0.6544	Remote Similarity	NPD8449	Approved
0.6541	Remote Similarity	NPD8074	Phase 3
0.6538	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6274	Approved
0.6532	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7625	Phase 1
0.6525	Remote Similarity	NPD4225	Approved
0.6525	Remote Similarity	NPD5696	Approved
0.6512	Remote Similarity	NPD7101	Approved
0.6512	Remote Similarity	NPD7100	Approved
0.65	Remote Similarity	NPD5225	Approved
0.65	Remote Similarity	NPD5226	Approved
0.65	Remote Similarity	NPD5224	Approved
0.65	Remote Similarity	NPD4633	Approved
0.65	Remote Similarity	NPD5211	Phase 2
0.6496	Remote Similarity	NPD8450	Suspended
0.6493	Remote Similarity	NPD8337	Approved
0.6493	Remote Similarity	NPD8336	Approved
0.6481	Remote Similarity	NPD7525	Registered
0.6476	Remote Similarity	NPD3702	Approved
0.6475	Remote Similarity	NPD4767	Approved
0.6475	Remote Similarity	NPD4768	Approved
0.6466	Remote Similarity	NPD7900	Approved
0.6466	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6903	Approved
0.6455	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD3669	Approved
0.6446	Remote Similarity	NPD5174	Approved
0.6446	Remote Similarity	NPD5175	Approved
0.6434	Remote Similarity	NPD6335	Approved
0.6429	Remote Similarity	NPD6409	Approved
0.6429	Remote Similarity	NPD7521	Approved
0.6429	Remote Similarity	NPD6684	Approved
0.6429	Remote Similarity	NPD5330	Approved
0.6429	Remote Similarity	NPD6053	Discontinued
0.6429	Remote Similarity	NPD7334	Approved
0.6429	Remote Similarity	NPD7146	Approved
0.6423	Remote Similarity	NPD8338	Approved
0.6417	Remote Similarity	NPD5223	Approved
0.6415	Remote Similarity	NPD7799	Discontinued
0.6412	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD6909	Approved
0.6412	Remote Similarity	NPD6908	Approved
0.641	Remote Similarity	NPD7991	Discontinued
0.6404	Remote Similarity	NPD5328	Approved
0.6404	Remote Similarity	NPD4753	Phase 2
0.6396	Remote Similarity	NPD4786	Approved
0.6393	Remote Similarity	NPD5141	Approved
0.6371	Remote Similarity	NPD4730	Approved
0.6371	Remote Similarity	NPD4729	Approved
0.6357	Remote Similarity	NPD6317	Approved
0.6325	Remote Similarity	NPD6001	Approved
0.6311	Remote Similarity	NPD4754	Approved
0.6308	Remote Similarity	NPD6314	Approved
0.6308	Remote Similarity	NPD6313	Approved
0.6293	Remote Similarity	NPD7637	Suspended
0.6293	Remote Similarity	NPD6079	Approved
0.6293	Remote Similarity	NPD6411	Approved
0.629	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6098	Approved
0.6283	Remote Similarity	NPD3618	Phase 1
0.6273	Remote Similarity	NPD1780	Approved
0.6273	Remote Similarity	NPD1779	Approved
0.627	Remote Similarity	NPD5251	Approved
0.627	Remote Similarity	NPD5250	Approved
0.627	Remote Similarity	NPD6371	Approved
0.627	Remote Similarity	NPD5247	Approved
0.627	Remote Similarity	NPD5248	Approved
0.627	Remote Similarity	NPD5249	Phase 3
0.6261	Remote Similarity	NPD6673	Approved
0.6261	Remote Similarity	NPD6080	Approved
0.6261	Remote Similarity	NPD6904	Approved
0.625	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD3666	Approved
0.625	Remote Similarity	NPD3133	Approved
0.624	Remote Similarity	NPD5128	Approved
0.6231	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD3667	Approved
0.619	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5777	Approved
0.6174	Remote Similarity	NPD5737	Approved
0.6174	Remote Similarity	NPD6672	Approved
0.6168	Remote Similarity	NPD3703	Phase 2
0.6154	Remote Similarity	NPD4267	Clinical (unspecified phase)

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