NPASS Compound

Structure

CID179429 OpenBabel06191715552D 66 74 0 0 1 0 0 0 0 0999 V2000 8.0430 0.0871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5410 -3.6718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2915 -1.3572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8216 -0.5444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9722 -0.9956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4659 -0.2367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0202 -1.8238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8248 1.3825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5689 -0.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7842 -1.3591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5680 0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5693 -2.7164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7849 -2.2641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7839 0.4532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7850 1.3581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5696 1.8108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1388 1.8104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0436 -0.8517 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3543 -4.1408 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5691 -0.0004 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9221 1.3572 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5683 -0.9055 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9059 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3532 -2.2632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3538 0.4523 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9219 0.4518 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8569 -1.3207 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3548 -5.0796 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8574 -2.2595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1681 -5.5485 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0446 -2.7293 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9809 -5.0787 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6048 -1.3225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6053 -2.2613 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7915 -0.8536 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7925 -2.7312 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7909 0.0852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2314 -2.2604 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9803 -4.1399 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9793 -2.2623 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7463 2.0365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3527 -1.3577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5618 -0.1885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7844 -1.3586 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7847 0.4527 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 -2.3541 1.3576 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6696 -0.8508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5421 -5.5494 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6707 -2.7284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1686 -6.4873 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0452 -3.6681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7942 -5.5476 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4175 -0.8527 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9776 0.5541 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6037 0.5551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2771 2.8497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7548 -0.5989 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2308 -1.3216 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1670 -3.6709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5303 2.0363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1665 -2.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4186 -2.7303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9787 -1.3235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7931 -3.6700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 43 1 0 0 0 0 4 43 1 0 0 0 0 5 44 1 0 0 0 0 6 44 1 0 0 0 0 8 46 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 24 1 0 0 0 0 12 15 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 45 1 0 0 0 0 15 47 1 0 0 0 0 16 17 1 0 0 0 0 16 46 1 0 0 0 0 18 48 1 0 0 0 0 19 1 1 1 0 0 0 19 28 1 0 0 0 0 19 60 1 0 0 0 0 20 2 1 6 0 0 0 20 29 1 0 0 0 0 20 61 1 0 0 0 0 21 26 1 0 0 0 0 21 46 1 6 0 0 0 22 18 1 6 0 0 0 22 27 1 0 0 0 0 22 62 1 0 0 0 0 23 43 1 0 0 0 0 23 45 1 1 0 0 0 24 45 1 1 0 0 0 24 47 1 0 0 0 0 25 43 1 0 0 0 0 25 63 1 1 0 0 0 26 27 1 0 0 0 0 26 48 1 1 0 0 0 27 44 1 6 0 0 0 28 30 1 0 0 0 0 28 49 1 6 0 0 0 29 31 1 0 0 0 0 29 50 1 1 0 0 0 30 32 1 0 0 0 0 30 51 1 1 0 0 0 31 33 1 0 0 0 0 31 52 1 6 0 0 0 32 39 1 0 0 0 0 32 53 1 1 0 0 0 33 40 1 0 0 0 0 33 54 1 6 0 0 0 34 35 1 0 0 0 0 34 36 1 0 0 0 0 34 55 1 1 0 0 0 35 37 1 0 0 0 0 35 64 1 6 0 0 0 36 38 1 6 0 0 0 36 65 1 0 0 0 0 37 41 1 0 0 0 0 37 66 1 1 0 0 0 38 56 2 0 0 0 0 38 57 1 0 0 0 0 39 60 1 0 0 0 0 39 64 1 6 0 0 0 40 61 1 0 0 0 0 40 66 1 1 0 0 0 41 63 1 6 0 0 0 41 65 1 0 0 0 0 42 48 1 0 0 0 0 42 58 2 0 0 0 0 42 62 1 0 0 0 0 44 59 1 0 0 0 0 45 7 1 1 0 0 0 46 47 1 1 0 0 0 47 9 1 1 0 0 0 48 17 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	940.5
Volume:	914.707
LogP:	3.383
LogD:	2.431
LogS:	-3.363
# Rotatable Bonds:	8
TPSA:	280.82
# H-Bond Aceptor:	18
# H-Bond Donor:	9
# Rings:	9
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.123
Synthetic Accessibility Score:	7.616
Fsp3:	0.958
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:	-5.703
MDCK Permeability:	0.00018808140885084867
Pgp-inhibitor:	0.444
Pgp-substrate:	0.436
Human Intestinal Absorption (HIA):	0.809
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	81.77288055419922%
Volume Distribution (VD):	0.217
Pgp-substrate:	9.953574180603027%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.372
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.015

ADMET: Excretion

Clearance (CL):	0.626
Half-life (T1/2):	0.599

ADMET: Toxicity

hERG Blockers:	0.144
Human Hepatotoxicity (H-HT):	0.197
Drug-inuced Liver Injury (DILI):	0.294
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.219
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.106
Carcinogencity:	0.011
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.902

Download Data

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

Natural Product: NPC179429

Natural Product ID:	NPC179429
*Common Name:**	Stellatoside C
IUPAC Name:	n.a.
Synonyms:	stellatoside C
Standard InCHIKey:	ICJBPRUJVYMYLV-SFGODBEGSA-N
Standard InCHI:	InChI=1S/C48H76O18/c1-19-28(49)30(51)32(53)39(60-19)64-35-34(55)36(38(56)57)65-41(37(35)66-40-33(54)31(52)29(50)20(2)61-40)63-25-13-14-45(7)23(43(25,3)4)12-15-47(9)24(45)11-10-21-26-27(44(5,6)59)22-18-48(26,42(58)62-22)17-16-46(21,47)8/h19-37,39-41,49-55,59H,10-18H2,1-9H3,(H,56,57)/t19-,20-,21+,22-,23-,24+,25-,26-,27+,28-,29-,30+,31+,32+,33+,34-,35-,36-,37+,39-,40-,41+,45-,46+,47+,48+/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1[C@@H]([C@@H](C(=O)O)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O)O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC[C@@H]2[C@H]4[C@@H]([C@@H]5C[C@@]4(CC[C@@]32C)C(=O)O5)C(C)(C)O)C1(C)C)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047214
PubChem CID:	70694565
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene 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
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579873]
NPO32656	Stenocereus alamosensis	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22704889]
NPO32619	isolatocereus dumortieri	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22704889]
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26225905]
NPO18498	Arundo donax	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18498	Arundo donax	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18498	Arundo donax	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18498	Arundo donax	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23254	Monoclea forsteri	Species	Monocleaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	IC50	>	200000.0	nM	PMID[483569]

☑ 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 NPC179429 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	617
0.1-0.2	4291
0.2-0.3	9749
0.3-0.4	12214
0.4-0.5	7062
0.5-0.6	4487
0.6-0.7	2250
0.7-0.8	1647
0.8-0.85	289
0.85-0.9	65
0.9-0.95	25
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9533	High Similarity	NPC469824
0.9346	High Similarity	NPC228190
0.9346	High Similarity	NPC236753
0.9252	High Similarity	NPC469826
0.9159	High Similarity	NPC203974
0.9138	High Similarity	NPC273962
0.9	High Similarity	NPC473062
0.8972	High Similarity	NPC469827
0.8929	High Similarity	NPC477465
0.8929	High Similarity	NPC79193
0.8909	High Similarity	NPC470622
0.8899	High Similarity	NPC202898
0.8899	High Similarity	NPC475319
0.8899	High Similarity	NPC92890
0.8889	High Similarity	NPC215408
0.8818	High Similarity	NPC220836
0.8818	High Similarity	NPC473817
0.8818	High Similarity	NPC469825
0.8818	High Similarity	NPC94086
0.8818	High Similarity	NPC92297
0.8818	High Similarity	NPC233433
0.8818	High Similarity	NPC273002
0.8793	High Similarity	NPC470478
0.875	High Similarity	NPC157571
0.8727	High Similarity	NPC472079
0.8727	High Similarity	NPC207693
0.8649	High Similarity	NPC87393
0.8649	High Similarity	NPC22709
0.8636	High Similarity	NPC126753
0.8624	High Similarity	NPC267637
0.8611	High Similarity	NPC80191
0.8611	High Similarity	NPC310031
0.8584	High Similarity	NPC477489
0.8584	High Similarity	NPC477492
0.8571	High Similarity	NPC66513
0.8545	High Similarity	NPC184805
0.8545	High Similarity	NPC273189
0.8532	High Similarity	NPC107385
0.8522	High Similarity	NPC475490
0.8519	High Similarity	NPC477172
0.8519	High Similarity	NPC475574
0.8509	High Similarity	NPC97002
0.85	High Similarity	NPC104427
0.8482	Intermediate Similarity	NPC208333
0.8482	Intermediate Similarity	NPC227879
0.8468	Intermediate Similarity	NPC471430
0.8455	Intermediate Similarity	NPC88469
0.8455	Intermediate Similarity	NPC470167
0.844	Intermediate Similarity	NPC80640
0.844	Intermediate Similarity	NPC470172
0.843	Intermediate Similarity	NPC2757
0.843	Intermediate Similarity	NPC292290
0.8426	Intermediate Similarity	NPC20028
0.8411	Intermediate Similarity	NPC470591
0.8411	Intermediate Similarity	NPC472273
0.8407	Intermediate Similarity	NPC471431
0.8378	Intermediate Similarity	NPC158367
0.8378	Intermediate Similarity	NPC119628
0.8378	Intermediate Similarity	NPC158051
0.8364	Intermediate Similarity	NPC473406
0.8364	Intermediate Similarity	NPC471253
0.8349	Intermediate Similarity	NPC472081
0.8349	Intermediate Similarity	NPC476512
0.8349	Intermediate Similarity	NPC108227
0.8349	Intermediate Similarity	NPC178853
0.8348	Intermediate Similarity	NPC102619
0.8348	Intermediate Similarity	NPC146563
0.8333	Intermediate Similarity	NPC281148
0.8333	Intermediate Similarity	NPC235405
0.8333	Intermediate Similarity	NPC30735
0.8318	Intermediate Similarity	NPC304011
0.8318	Intermediate Similarity	NPC139271
0.8318	Intermediate Similarity	NPC238796
0.8318	Intermediate Similarity	NPC237071
0.8318	Intermediate Similarity	NPC203434
0.8304	Intermediate Similarity	NPC40716
0.8304	Intermediate Similarity	NPC475234
0.8304	Intermediate Similarity	NPC475630
0.8304	Intermediate Similarity	NPC138219
0.8291	Intermediate Similarity	NPC156651
0.8288	Intermediate Similarity	NPC327093
0.8273	Intermediate Similarity	NPC134967
0.8273	Intermediate Similarity	NPC310138
0.8273	Intermediate Similarity	NPC114700
0.8273	Intermediate Similarity	NPC470029
0.8264	Intermediate Similarity	NPC470477
0.8257	Intermediate Similarity	NPC80417
0.825	Intermediate Similarity	NPC235438
0.825	Intermediate Similarity	NPC40775
0.825	Intermediate Similarity	NPC249848
0.825	Intermediate Similarity	NPC131824
0.825	Intermediate Similarity	NPC107966
0.8241	Intermediate Similarity	NPC210157
0.823	Intermediate Similarity	NPC231566
0.823	Intermediate Similarity	NPC473688
0.823	Intermediate Similarity	NPC471626
0.823	Intermediate Similarity	NPC262567
0.8224	Intermediate Similarity	NPC215570
0.8214	Intermediate Similarity	NPC166079
0.8214	Intermediate Similarity	NPC306776
0.8205	Intermediate Similarity	NPC469823
0.8205	Intermediate Similarity	NPC469820
0.8205	Intermediate Similarity	NPC137414
0.8198	Intermediate Similarity	NPC476837
0.8198	Intermediate Similarity	NPC139181
0.8198	Intermediate Similarity	NPC97260
0.8198	Intermediate Similarity	NPC34562
0.8197	Intermediate Similarity	NPC470218
0.8182	Intermediate Similarity	NPC476839
0.8182	Intermediate Similarity	NPC476838
0.8182	Intermediate Similarity	NPC228701
0.8175	Intermediate Similarity	NPC478069
0.8174	Intermediate Similarity	NPC11035
0.8174	Intermediate Similarity	NPC204392
0.8174	Intermediate Similarity	NPC91838
0.8174	Intermediate Similarity	NPC240734
0.8174	Intermediate Similarity	NPC275668
0.8174	Intermediate Similarity	NPC1876
0.8174	Intermediate Similarity	NPC272242
0.8167	Intermediate Similarity	NPC159309
0.8167	Intermediate Similarity	NPC64715
0.8167	Intermediate Similarity	NPC11242
0.8167	Intermediate Similarity	NPC301449
0.8167	Intermediate Similarity	NPC171544
0.8167	Intermediate Similarity	NPC22956
0.8167	Intermediate Similarity	NPC114484
0.8167	Intermediate Similarity	NPC31838
0.8167	Intermediate Similarity	NPC222580
0.8167	Intermediate Similarity	NPC223301
0.8167	Intermediate Similarity	NPC297263
0.8167	Intermediate Similarity	NPC62725
0.8167	Intermediate Similarity	NPC86222
0.8167	Intermediate Similarity	NPC104372
0.8148	Intermediate Similarity	NPC116683
0.8148	Intermediate Similarity	NPC476728
0.8148	Intermediate Similarity	NPC121453
0.8148	Intermediate Similarity	NPC296936
0.8131	Intermediate Similarity	NPC291547
0.8131	Intermediate Similarity	NPC131693
0.8131	Intermediate Similarity	NPC45959
0.8131	Intermediate Similarity	NPC291203
0.8131	Intermediate Similarity	NPC473851
0.8131	Intermediate Similarity	NPC475436
0.8131	Intermediate Similarity	NPC253268
0.8131	Intermediate Similarity	NPC179859
0.8131	Intermediate Similarity	NPC217205
0.8131	Intermediate Similarity	NPC305418
0.8131	Intermediate Similarity	NPC174024
0.8131	Intermediate Similarity	NPC312678
0.8131	Intermediate Similarity	NPC252253
0.8125	Intermediate Similarity	NPC100078
0.812	Intermediate Similarity	NPC470115
0.812	Intermediate Similarity	NPC470116
0.812	Intermediate Similarity	NPC54395
0.8115	Intermediate Similarity	NPC130229
0.8108	Intermediate Similarity	NPC244969
0.8108	Intermediate Similarity	NPC213528
0.8108	Intermediate Similarity	NPC471254
0.8099	Intermediate Similarity	NPC21691
0.8099	Intermediate Similarity	NPC162574
0.8099	Intermediate Similarity	NPC236870
0.8099	Intermediate Similarity	NPC475591
0.8099	Intermediate Similarity	NPC213952
0.8099	Intermediate Similarity	NPC4749
0.8099	Intermediate Similarity	NPC80986
0.8099	Intermediate Similarity	NPC187290
0.8099	Intermediate Similarity	NPC10607
0.8091	Intermediate Similarity	NPC41843
0.8087	Intermediate Similarity	NPC106760
0.8083	Intermediate Similarity	NPC236657
0.8083	Intermediate Similarity	NPC118440
0.8083	Intermediate Similarity	NPC108072
0.8073	Intermediate Similarity	NPC476112
0.8073	Intermediate Similarity	NPC471241
0.8073	Intermediate Similarity	NPC477223
0.8073	Intermediate Similarity	NPC274200
0.8073	Intermediate Similarity	NPC307534
0.8073	Intermediate Similarity	NPC477222
0.807	Intermediate Similarity	NPC316930
0.8067	Intermediate Similarity	NPC469822
0.8056	Intermediate Similarity	NPC475351
0.8056	Intermediate Similarity	NPC305808
0.8056	Intermediate Similarity	NPC19400
0.8056	Intermediate Similarity	NPC206003
0.8056	Intermediate Similarity	NPC94582
0.8056	Intermediate Similarity	NPC474399
0.8056	Intermediate Similarity	NPC57964
0.8056	Intermediate Similarity	NPC211354
0.8056	Intermediate Similarity	NPC107962
0.8056	Intermediate Similarity	NPC107188
0.8056	Intermediate Similarity	NPC473610
0.8056	Intermediate Similarity	NPC6295
0.8056	Intermediate Similarity	NPC473727
0.8049	Intermediate Similarity	NPC469947
0.8049	Intermediate Similarity	NPC285091
0.8049	Intermediate Similarity	NPC181066
0.8037	Intermediate Similarity	NPC477547
0.8037	Intermediate Similarity	NPC141769
0.8037	Intermediate Similarity	NPC234352
0.8037	Intermediate Similarity	NPC149400

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 NPC179429 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	659
0.1-0.2	4085
0.2-0.3	2940
0.3-0.4	828
0.4-0.5	321
0.5-0.6	213
0.6-0.7	78
0.7-0.8	23
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8796	High Similarity	NPD8170	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD8171	Discontinued
0.7886	Intermediate Similarity	NPD8328	Phase 3
0.7881	Intermediate Similarity	NPD8133	Approved
0.7778	Intermediate Similarity	NPD7736	Approved
0.7559	Intermediate Similarity	NPD8293	Discontinued
0.7442	Intermediate Similarity	NPD7319	Approved
0.7391	Intermediate Similarity	NPD1700	Approved
0.7381	Intermediate Similarity	NPD6370	Approved
0.735	Intermediate Similarity	NPD4057	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD4056	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7507	Approved
0.7266	Intermediate Similarity	NPD7492	Approved
0.7222	Intermediate Similarity	NPD8377	Approved
0.7222	Intermediate Similarity	NPD6054	Approved
0.7222	Intermediate Similarity	NPD6059	Approved
0.7222	Intermediate Similarity	NPD8294	Approved
0.7209	Intermediate Similarity	NPD6616	Approved
0.7165	Intermediate Similarity	NPD8296	Approved
0.7165	Intermediate Similarity	NPD8380	Approved
0.7165	Intermediate Similarity	NPD8379	Approved
0.7165	Intermediate Similarity	NPD8335	Approved
0.7165	Intermediate Similarity	NPD8378	Approved
0.7154	Intermediate Similarity	NPD7078	Approved
0.7107	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6015	Approved
0.7031	Intermediate Similarity	NPD8033	Approved
0.7031	Intermediate Similarity	NPD6016	Approved
0.6977	Remote Similarity	NPD5988	Approved
0.6953	Remote Similarity	NPD6319	Approved
0.6916	Remote Similarity	NPD6928	Phase 2
0.6885	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.68	Remote Similarity	NPD8297	Approved
0.68	Remote Similarity	NPD6882	Approved
0.6797	Remote Similarity	NPD7328	Approved
0.6797	Remote Similarity	NPD7327	Approved
0.6772	Remote Similarity	NPD6940	Discontinued
0.6769	Remote Similarity	NPD8513	Phase 3
0.6769	Remote Similarity	NPD8516	Approved
0.6769	Remote Similarity	NPD8515	Approved
0.6769	Remote Similarity	NPD8517	Approved
0.6744	Remote Similarity	NPD7516	Approved
0.6729	Remote Similarity	NPD6697	Approved
0.6729	Remote Similarity	NPD6115	Approved
0.6729	Remote Similarity	NPD6118	Approved
0.6729	Remote Similarity	NPD6114	Approved
0.6719	Remote Similarity	NPD6009	Approved
0.6716	Remote Similarity	NPD6033	Approved
0.6694	Remote Similarity	NPD6372	Approved
0.6694	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD7329	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6636	Remote Similarity	NPD6116	Phase 1
0.6613	Remote Similarity	NPD7320	Approved
0.6587	Remote Similarity	NPD6649	Approved
0.6587	Remote Similarity	NPD6650	Approved
0.6585	Remote Similarity	NPD6675	Approved
0.6585	Remote Similarity	NPD6402	Approved
0.6585	Remote Similarity	NPD7128	Approved
0.6585	Remote Similarity	NPD5739	Approved
0.6577	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD3669	Approved
0.6552	Remote Similarity	NPD8034	Phase 2
0.6552	Remote Similarity	NPD8035	Phase 2
0.6545	Remote Similarity	NPD1780	Approved
0.6545	Remote Similarity	NPD1779	Approved
0.6542	Remote Similarity	NPD6117	Approved
0.6484	Remote Similarity	NPD4632	Approved
0.648	Remote Similarity	NPD6881	Approved
0.648	Remote Similarity	NPD6899	Approved
0.6457	Remote Similarity	NPD8130	Phase 1
0.6449	Remote Similarity	NPD3702	Approved
0.64	Remote Similarity	NPD5701	Approved
0.64	Remote Similarity	NPD5697	Approved
0.6391	Remote Similarity	NPD6921	Approved
0.6391	Remote Similarity	NPD7503	Approved
0.6378	Remote Similarity	NPD7102	Approved
0.6378	Remote Similarity	NPD7290	Approved
0.6378	Remote Similarity	NPD6883	Approved
0.6355	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD8139	Approved
0.6341	Remote Similarity	NPD8083	Approved
0.6341	Remote Similarity	NPD8085	Approved
0.6341	Remote Similarity	NPD8084	Approved
0.6341	Remote Similarity	NPD8086	Approved
0.6341	Remote Similarity	NPD8138	Approved
0.6341	Remote Similarity	NPD8082	Approved
0.6328	Remote Similarity	NPD6869	Approved
0.6328	Remote Similarity	NPD6617	Approved
0.6328	Remote Similarity	NPD6847	Approved
0.632	Remote Similarity	NPD8393	Approved
0.6299	Remote Similarity	NPD6014	Approved
0.6299	Remote Similarity	NPD6013	Approved
0.6299	Remote Similarity	NPD6012	Approved
0.6296	Remote Similarity	NPD3703	Phase 2
0.6296	Remote Similarity	NPD7604	Phase 2
0.629	Remote Similarity	NPD8275	Approved
0.629	Remote Similarity	NPD8276	Approved
0.6269	Remote Similarity	NPD5983	Phase 2
0.625	Remote Similarity	NPD7991	Discontinued
0.625	Remote Similarity	NPD4634	Approved
0.624	Remote Similarity	NPD8081	Approved
0.622	Remote Similarity	NPD6011	Approved
0.622	Remote Similarity	NPD6686	Approved
0.6204	Remote Similarity	NPD6336	Discontinued
0.6202	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6008	Approved
0.6174	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6067	Discontinued
0.6028	Remote Similarity	NPD5956	Approved
0.6019	Remote Similarity	NPD5777	Approved
0.6019	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD8140	Approved
0.6016	Remote Similarity	NPD4755	Approved
0.6016	Remote Similarity	NPD6083	Phase 2
0.6016	Remote Similarity	NPD6084	Phase 2
0.6016	Remote Similarity	NPD8307	Discontinued
0.6015	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD7100	Approved
0.6	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD7799	Discontinued
0.5982	Remote Similarity	NPD4238	Approved
0.5982	Remote Similarity	NPD4802	Phase 2
0.5981	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.597	Remote Similarity	NPD7115	Discovery
0.5963	Remote Similarity	NPD3181	Approved
0.5952	Remote Similarity	NPD8301	Approved
0.5952	Remote Similarity	NPD8300	Approved
0.5929	Remote Similarity	NPD8074	Phase 3
0.5926	Remote Similarity	NPD6335	Approved
0.5926	Remote Similarity	NPD4245	Approved
0.5926	Remote Similarity	NPD4244	Approved
0.5926	Remote Similarity	NPD4789	Approved
0.5923	Remote Similarity	NPD8305	Approved
0.5923	Remote Similarity	NPD8306	Approved
0.592	Remote Similarity	NPD4700	Approved
0.592	Remote Similarity	NPD5285	Approved
0.592	Remote Similarity	NPD5286	Approved
0.592	Remote Similarity	NPD4696	Approved
0.5912	Remote Similarity	NPD6909	Approved
0.5912	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD6908	Approved
0.5912	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD1811	Approved
0.5909	Remote Similarity	NPD1810	Approved
0.5903	Remote Similarity	NPD8450	Suspended
0.5887	Remote Similarity	NPD7902	Approved
0.5878	Remote Similarity	NPD8087	Discontinued
0.587	Remote Similarity	NPD8080	Discontinued
0.5852	Remote Similarity	NPD6317	Approved
0.584	Remote Similarity	NPD5696	Approved
0.584	Remote Similarity	NPD7638	Approved
0.5833	Remote Similarity	NPD3698	Phase 2
0.5833	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8449	Approved
0.5833	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD5225	Approved
0.5827	Remote Similarity	NPD5226	Approved
0.5827	Remote Similarity	NPD5211	Phase 2
0.5827	Remote Similarity	NPD5224	Approved
0.5827	Remote Similarity	NPD4633	Approved
0.5814	Remote Similarity	NPD4768	Approved
0.5814	Remote Similarity	NPD4767	Approved
0.5809	Remote Similarity	NPD6313	Approved
0.5809	Remote Similarity	NPD6314	Approved
0.5802	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7639	Approved
0.5794	Remote Similarity	NPD897	Approved
0.5794	Remote Similarity	NPD8418	Phase 2
0.5794	Remote Similarity	NPD896	Approved
0.5794	Remote Similarity	NPD7640	Approved
0.5794	Remote Similarity	NPD898	Approved
0.5781	Remote Similarity	NPD5175	Approved
0.5781	Remote Similarity	NPD5174	Approved
0.5772	Remote Similarity	NPD7748	Approved
0.5769	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD7625	Phase 1
0.5748	Remote Similarity	NPD5223	Approved
0.5741	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD5360	Phase 3
0.5736	Remote Similarity	NPD5141	Approved
0.5735	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6081	Approved
0.5726	Remote Similarity	NPD5695	Phase 3
0.5725	Remote Similarity	NPD4730	Approved
0.5725	Remote Similarity	NPD4729	Approved
0.5725	Remote Similarity	NPD8346	Approved
0.5725	Remote Similarity	NPD8347	Approved
0.5725	Remote Similarity	NPD8345	Approved
0.5703	Remote Similarity	NPD7632	Discontinued
0.5691	Remote Similarity	NPD6399	Phase 3
0.5664	Remote Similarity	NPD8336	Approved
0.5664	Remote Similarity	NPD8337	Approved
0.5659	Remote Similarity	NPD4754	Approved
0.5645	Remote Similarity	NPD7900	Approved
0.5645	Remote Similarity	NPD7901	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