NPASS Compound

Structure

NPC149966 OpenBabel07101718332D 52 57 0 0 1 0 0 0 0 0999 V2000 1.0563 2.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6962 0.8443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0006 -0.0422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6807 1.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0388 -4.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0388 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 3.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1346 0.4578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7326 -1.0422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2685 0.9578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8666 -0.5422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8666 2.4578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9321 3.5405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0388 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3872 1.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 2.4190 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0006 1.9578 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0006 0.9578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5254 2.6270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5987 -0.5422 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7326 1.9578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9266 3.4360 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5909 2.0032 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0388 -3.0981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1346 2.4578 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7326 0.9578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5987 0.4578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5388 -2.2321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0388 -1.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0388 -1.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8666 0.4578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2685 1.9578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7045 -2.5823 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4647 -1.0422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5987 2.4578 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5958 4.1791 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4647 0.9578 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5388 -2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5388 -3.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 6 47 1 0 0 0 0 7 48 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 39 1 0 0 0 0 13 38 1 0 0 0 0 14 24 1 0 0 0 0 15 22 1 0 0 0 0 15 25 1 0 0 0 0 16 40 1 0 0 0 0 17 28 1 0 0 0 0 17 49 1 0 0 0 0 18 26 1 0 0 0 0 19 3 1 1 0 0 0 19 22 1 0 0 0 0 20 14 1 1 0 0 0 20 21 1 0 0 0 0 20 29 1 0 0 0 0 21 38 1 6 0 0 0 22 39 1 6 0 0 0 23 31 1 0 0 0 0 23 41 1 6 0 0 0 24 30 1 0 0 0 0 24 42 1 1 0 0 0 25 29 1 0 0 0 0 25 43 1 6 0 0 0 26 9 1 1 0 0 0 26 50 1 0 0 0 0 27 16 1 6 0 0 0 27 32 1 0 0 0 0 27 51 1 0 0 0 0 28 33 1 0 0 0 0 28 47 1 1 0 0 0 29 39 1 6 0 0 0 30 31 1 0 0 0 0 30 38 1 6 0 0 0 31 44 1 6 0 0 0 32 35 1 0 0 0 0 32 45 1 6 0 0 0 33 34 1 0 0 0 0 33 46 1 6 0 0 0 34 36 1 0 0 0 0 34 48 1 1 0 0 0 35 37 1 0 0 0 0 35 52 1 1 0 0 0 36 49 1 0 0 0 0 36 52 1 6 0 0 0 37 50 1 6 0 0 0 37 51 1 0 0 0 0 38 4 1 6 0 0 0 39 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	744.47
Volume:	746.034
LogP:	3.558
LogD:	4.029
LogS:	-3.275
# Rotatable Bonds:	12
TPSA:	196.99
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.152
Synthetic Accessibility Score:	5.957
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:	-5.42
MDCK Permeability:	0.00011817996710306033
Pgp-inhibitor:	0.995
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.695
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	72.58259582519531%
Volume Distribution (VD):	0.341
Pgp-substrate:	8.773179054260254%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.169
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.408
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	1.227
Half-life (T1/2):	0.672

ADMET: Toxicity

hERG Blockers:	0.895
Human Hepatotoxicity (H-HT):	0.122
Drug-inuced Liver Injury (DILI):	0.164
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.94
Carcinogencity:	0.031
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC149966

Natural Product ID:	NPC149966
*Common Name:**	Certonardoside I
IUPAC Name:	(3S,4R,5S,6S,8R,9S,10R,13R,14S,15R,17R)-17-[(2R,5S)-5-[(2R,3R,4S,5R)-4-hydroxy-3-[(2S,3R,4S,5R)-4-hydroxy-3,5-dimethoxyoxan-2-yl]oxy-5-(hydroxymethyl)oxolan-2-yl]oxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,4,6,15-tetrol
Synonyms:	Certonardoside I
Standard InCHIKey:	NYZYTLFOAUNRRR-YOXBRCCASA-N
Standard InCHI:	InChI=1S/C39H68O13/c1-18(2)26(50-37-35(32(45)27(16-40)51-37)52-36-34(48-7)33(46)28(47-6)17-49-36)9-8-19(3)22-15-25(43)29-20-14-24(42)30-31(44)23(41)11-13-38(30,4)21(20)10-12-39(22,29)5/h18-37,40-46H,8-17H2,1-7H3/t19-,20-,21+,22-,23+,24+,25-,26+,27-,28-,29-,30+,31+,32+,33+,34-,35-,36+,37-,38-,39-/m1/s1
SMILES:	CC(C)[C@H](CC[C@@H](C)[C@H]1C[C@H]([C@H]2[C@@H]3C[C@@H]([C@H]4[C@H]([C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO)O1)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452695
PubChem CID:	505377
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444692]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662097]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104487]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497935]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	7
Others	3

Activity Type	# Activity
Cell Line	3
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	CC50	=	59.9	ug.mL-1	PMID[496420]
NPT25	Cell Line	MT4	Homo sapiens	CC50	=	42.5	ug.mL-1	PMID[496420]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	>	100.0	ug.mL-1	PMID[496420]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	EC50	>	100.0	ug.mL-1	PMID[496420]
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	EC50	>	100.0	ug.mL-1	PMID[496420]
NPT3119	Organism	Human coxsackievirus B3	Human coxsackievirus B3	EC50	>	59.9	ug.mL-1	PMID[496420]
NPT4337	Organism	Encephalomyocarditis virus	Encephalomyocarditis virus	EC50	>	59.9	ug.mL-1	PMID[496420]
NPT2516	Organism	Vesicular stomatitis Indiana virus	Vesicular stomatitis Indiana virus	EC50	>	59.9	ug.mL-1	PMID[496420]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	42.5	ug.mL-1	PMID[496420]
NPT3795	Organism	Human immunodeficiency virus 2	Human immunodeficiency virus 2	EC50	>	42.5	ug.mL-1	PMID[496420]

☑ 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 NPC149966 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	542
0.1-0.2	4817
0.2-0.3	13481
0.3-0.4	10722
0.4-0.5	5649
0.5-0.6	3707
0.6-0.7	2407
0.7-0.8	933
0.8-0.85	221
0.85-0.9	73
0.9-0.95	131
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC5632
0.9882	High Similarity	NPC473542
0.977	High Similarity	NPC3538
0.977	High Similarity	NPC113500
0.977	High Similarity	NPC477224
0.9765	High Similarity	NPC473472
0.9765	High Similarity	NPC20822
0.9655	High Similarity	NPC149400
0.9655	High Similarity	NPC311246
0.9655	High Similarity	NPC167644
0.9655	High Similarity	NPC88962
0.9655	High Similarity	NPC144790
0.9651	High Similarity	NPC223143
0.9647	High Similarity	NPC281004
0.9551	High Similarity	NPC121453
0.9545	High Similarity	NPC179859
0.9545	High Similarity	NPC174024
0.9545	High Similarity	NPC45959
0.9545	High Similarity	NPC473774
0.9545	High Similarity	NPC312678
0.9545	High Similarity	NPC175
0.9545	High Similarity	NPC291547
0.9545	High Similarity	NPC131693
0.9545	High Similarity	NPC475436
0.9545	High Similarity	NPC222731
0.9545	High Similarity	NPC253268
0.9545	High Similarity	NPC294686
0.9545	High Similarity	NPC24960
0.9545	High Similarity	NPC473851
0.9545	High Similarity	NPC252253
0.954	High Similarity	NPC293609
0.9535	High Similarity	NPC82955
0.9535	High Similarity	NPC102725
0.9444	High Similarity	NPC477222
0.9444	High Similarity	NPC477223
0.9438	High Similarity	NPC473067
0.9438	High Similarity	NPC473065
0.9438	High Similarity	NPC473064
0.9432	High Similarity	NPC48339
0.9432	High Similarity	NPC477451
0.9432	High Similarity	NPC477547
0.9432	High Similarity	NPC250393
0.9432	High Similarity	NPC177834
0.9432	High Similarity	NPC249204
0.9432	High Similarity	NPC141769
0.9432	High Similarity	NPC325828
0.9432	High Similarity	NPC277774
0.9432	High Similarity	NPC476669
0.9432	High Similarity	NPC234352
0.9432	High Similarity	NPC297348
0.9425	High Similarity	NPC65550
0.9425	High Similarity	NPC279329
0.9341	High Similarity	NPC473518
0.9341	High Similarity	NPC473638
0.9333	High Similarity	NPC195297
0.9333	High Similarity	NPC473601
0.9333	High Similarity	NPC304011
0.9333	High Similarity	NPC476510
0.9333	High Similarity	NPC139271
0.9333	High Similarity	NPC142264
0.9326	High Similarity	NPC291203
0.9326	High Similarity	NPC471464
0.9326	High Similarity	NPC264101
0.9326	High Similarity	NPC217205
0.9326	High Similarity	NPC475325
0.9318	High Similarity	NPC307167
0.9318	High Similarity	NPC473637
0.9318	High Similarity	NPC204881
0.9318	High Similarity	NPC473830
0.9318	High Similarity	NPC36372
0.9318	High Similarity	NPC229801
0.9318	High Similarity	NPC476668
0.9318	High Similarity	NPC210759
0.9302	High Similarity	NPC43912
0.9302	High Similarity	NPC140446
0.9294	High Similarity	NPC273290
0.9294	High Similarity	NPC232044
0.9231	High Similarity	NPC307534
0.9231	High Similarity	NPC470861
0.9231	High Similarity	NPC115165
0.9231	High Similarity	NPC51520
0.9231	High Similarity	NPC475207
0.9231	High Similarity	NPC233649
0.9231	High Similarity	NPC303069
0.9231	High Similarity	NPC83137
0.9231	High Similarity	NPC470862
0.9231	High Similarity	NPC476112
0.9231	High Similarity	NPC470028
0.9231	High Similarity	NPC232611
0.9222	High Similarity	NPC19400
0.9222	High Similarity	NPC107962
0.9222	High Similarity	NPC473727
0.9222	High Similarity	NPC211354
0.9222	High Similarity	NPC475351
0.9222	High Similarity	NPC92196
0.9222	High Similarity	NPC474399
0.9222	High Similarity	NPC107188
0.9222	High Similarity	NPC206003
0.9222	High Similarity	NPC473610
0.9222	High Similarity	NPC6295
0.9213	High Similarity	NPC172838
0.9213	High Similarity	NPC137004
0.9213	High Similarity	NPC473726
0.9176	High Similarity	NPC227260
0.914	High Similarity	NPC477225
0.913	High Similarity	NPC291548
0.913	High Similarity	NPC473616
0.9121	High Similarity	NPC473287
0.9121	High Similarity	NPC232037
0.9121	High Similarity	NPC184617
0.9121	High Similarity	NPC475625
0.9121	High Similarity	NPC98018
0.9121	High Similarity	NPC470863
0.9121	High Similarity	NPC132080
0.9121	High Similarity	NPC470865
0.9121	High Similarity	NPC470864
0.9121	High Similarity	NPC97700
0.9121	High Similarity	NPC160426
0.9121	High Similarity	NPC103616
0.9121	High Similarity	NPC128572
0.9121	High Similarity	NPC30856
0.9121	High Similarity	NPC475643
0.9121	High Similarity	NPC84111
0.9121	High Similarity	NPC284104
0.9121	High Similarity	NPC287483
0.9121	High Similarity	NPC116756
0.9121	High Similarity	NPC470866
0.9111	High Similarity	NPC309866
0.9111	High Similarity	NPC305418
0.9111	High Similarity	NPC473503
0.9111	High Similarity	NPC30687
0.9101	High Similarity	NPC59006
0.9091	High Similarity	NPC131466
0.907	High Similarity	NPC290612
0.9022	High Similarity	NPC274200
0.9011	High Similarity	NPC469710
0.8977	High Similarity	NPC128475
0.8966	High Similarity	NPC471240
0.8941	High Similarity	NPC296734
0.8941	High Similarity	NPC470611
0.8936	High Similarity	NPC475574
0.8936	High Similarity	NPC472081
0.8936	High Similarity	NPC108227
0.8936	High Similarity	NPC476512
0.8913	High Similarity	NPC296936
0.8913	High Similarity	NPC238796
0.8913	High Similarity	NPC203434
0.8913	High Similarity	NPC237071
0.8876	High Similarity	NPC228059
0.8864	High Similarity	NPC161928
0.8864	High Similarity	NPC210658
0.8864	High Similarity	NPC472396
0.8842	High Similarity	NPC114700
0.8842	High Similarity	NPC470029
0.8842	High Similarity	NPC134967
0.8842	High Similarity	NPC310138
0.883	High Similarity	NPC470030
0.8817	High Similarity	NPC470591
0.8804	High Similarity	NPC94582
0.8804	High Similarity	NPC57964
0.8804	High Similarity	NPC477494
0.875	High Similarity	NPC476837
0.875	High Similarity	NPC97260
0.875	High Similarity	NPC139181
0.8737	High Similarity	NPC31346
0.8723	High Similarity	NPC292775
0.871	High Similarity	NPC156377
0.8706	High Similarity	NPC248944
0.8706	High Similarity	NPC7479
0.8706	High Similarity	NPC257296
0.8696	High Similarity	NPC151214
0.8696	High Similarity	NPC191915
0.866	High Similarity	NPC475365
0.8632	High Similarity	NPC41843
0.8617	High Similarity	NPC210157
0.8587	High Similarity	NPC182740
0.8587	High Similarity	NPC211845
0.8587	High Similarity	NPC256104
0.8587	High Similarity	NPC122083
0.8542	High Similarity	NPC477172
0.8542	High Similarity	NPC476839
0.8542	High Similarity	NPC476838
0.8523	High Similarity	NPC474156
0.8511	High Similarity	NPC472989
0.8511	High Similarity	NPC252056
0.8485	Intermediate Similarity	NPC54619
0.8469	Intermediate Similarity	NPC475521
0.8469	Intermediate Similarity	NPC312774
0.8438	Intermediate Similarity	NPC20028
0.8421	Intermediate Similarity	NPC76486
0.8409	Intermediate Similarity	NPC470070
0.8409	Intermediate Similarity	NPC241959
0.8404	Intermediate Similarity	NPC21897
0.8387	Intermediate Similarity	NPC224003
0.8387	Intermediate Similarity	NPC171741
0.8387	Intermediate Similarity	NPC470623
0.8387	Intermediate Similarity	NPC18724
0.8387	Intermediate Similarity	NPC323231
0.8384	Intermediate Similarity	NPC215408
0.8367	Intermediate Similarity	NPC213190

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 NPC149966 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	520
0.1-0.2	4518
0.2-0.3	2896
0.3-0.4	631
0.4-0.5	322
0.5-0.6	195
0.6-0.7	51
0.7-0.8	14
0.8-0.85	0
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9432	High Similarity	NPD8171	Discontinued
0.8706	High Similarity	NPD6928	Phase 2
0.8469	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD7991	Discontinued
0.7477	Intermediate Similarity	NPD7516	Approved
0.7411	Intermediate Similarity	NPD8294	Approved
0.7411	Intermediate Similarity	NPD8377	Approved
0.7387	Intermediate Similarity	NPD7327	Approved
0.7387	Intermediate Similarity	NPD7328	Approved
0.7345	Intermediate Similarity	NPD8033	Approved
0.7345	Intermediate Similarity	NPD8378	Approved
0.7345	Intermediate Similarity	NPD8380	Approved
0.7345	Intermediate Similarity	NPD8379	Approved
0.7345	Intermediate Similarity	NPD8296	Approved
0.7345	Intermediate Similarity	NPD8335	Approved
0.7326	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8133	Approved
0.7	Intermediate Similarity	NPD1811	Approved
0.7	Intermediate Similarity	NPD1810	Approved
0.6972	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7507	Approved
0.6944	Remote Similarity	NPD6412	Phase 2
0.6854	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7319	Approved
0.6754	Remote Similarity	NPD6940	Discontinued
0.6752	Remote Similarity	NPD7503	Approved
0.6727	Remote Similarity	NPD8174	Phase 2
0.6702	Remote Similarity	NPD6115	Approved
0.6702	Remote Similarity	NPD6118	Approved
0.6702	Remote Similarity	NPD6114	Approved
0.6702	Remote Similarity	NPD6697	Approved
0.6694	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD4787	Phase 1
0.6667	Remote Similarity	NPD2254	Approved
0.6667	Remote Similarity	NPD2687	Approved
0.6667	Remote Similarity	NPD2686	Approved
0.6596	Remote Similarity	NPD6116	Phase 1
0.6555	Remote Similarity	NPD6370	Approved
0.6552	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD371	Approved
0.6531	Remote Similarity	NPD3669	Approved
0.6531	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6117	Approved
0.648	Remote Similarity	NPD8449	Approved
0.6475	Remote Similarity	NPD8293	Discontinued
0.6429	Remote Similarity	NPD8450	Suspended
0.6387	Remote Similarity	NPD6054	Approved
0.6387	Remote Similarity	NPD6059	Approved
0.6277	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.623	Remote Similarity	NPD8328	Phase 3
0.623	Remote Similarity	NPD6067	Discontinued
0.6224	Remote Similarity	NPD7525	Registered
0.6211	Remote Similarity	NPD3703	Phase 2
0.6198	Remote Similarity	NPD6015	Approved
0.6198	Remote Similarity	NPD6016	Approved
0.619	Remote Similarity	NPD8034	Phase 2
0.619	Remote Similarity	NPD8035	Phase 2
0.6182	Remote Similarity	NPD1700	Approved
0.6179	Remote Similarity	NPD7492	Approved
0.6148	Remote Similarity	NPD5988	Approved
0.614	Remote Similarity	NPD6686	Approved
0.6129	Remote Similarity	NPD6616	Approved
0.6129	Remote Similarity	NPD4245	Approved
0.6129	Remote Similarity	NPD4244	Approved
0.608	Remote Similarity	NPD7078	Approved
0.6042	Remote Similarity	NPD3702	Approved
0.6022	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD3698	Phase 2
0.6018	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7638	Approved
0.5985	Remote Similarity	NPD7625	Phase 1
0.5962	Remote Similarity	NPD7524	Approved
0.5946	Remote Similarity	NPD7639	Approved
0.5946	Remote Similarity	NPD7640	Approved
0.5932	Remote Similarity	NPD8297	Approved
0.5932	Remote Similarity	NPD6882	Approved
0.593	Remote Similarity	NPD2267	Suspended
0.5922	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD6033	Approved
0.5895	Remote Similarity	NPD5777	Approved
0.5868	Remote Similarity	NPD6009	Approved
0.5865	Remote Similarity	NPD8308	Discontinued
0.5862	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD6319	Approved
0.5843	Remote Similarity	NPD6123	Approved
0.5842	Remote Similarity	NPD1779	Approved
0.5842	Remote Similarity	NPD1780	Approved
0.5841	Remote Similarity	NPD7632	Discontinued
0.58	Remote Similarity	NPD7645	Phase 2
0.5794	Remote Similarity	NPD6700	Approved
0.5794	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4789	Approved
0.5765	Remote Similarity	NPD894	Approved
0.5765	Remote Similarity	NPD889	Approved
0.5765	Remote Similarity	NPD887	Approved
0.5765	Remote Similarity	NPD895	Approved
0.5752	Remote Similarity	NPD4159	Approved
0.575	Remote Similarity	NPD4632	Approved
0.5745	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD5360	Phase 3
0.5741	Remote Similarity	NPD6702	Approved
0.5741	Remote Similarity	NPD6703	Approved
0.5726	Remote Similarity	NPD7320	Approved
0.569	Remote Similarity	NPD7128	Approved
0.569	Remote Similarity	NPD6402	Approved
0.569	Remote Similarity	NPD5739	Approved
0.569	Remote Similarity	NPD6675	Approved
0.5678	Remote Similarity	NPD6373	Approved
0.5678	Remote Similarity	NPD6372	Approved
0.5678	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD8418	Phase 2
0.5657	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD2269	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