NPASS Compound

Structure

NPC471119 OpenBabel07101719252D 45 48 0 0 1 0 0 0 0 0999 V2000 2.2382 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6984 3.7985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9552 4.4677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2942 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 1.2601 0.0000 C 0 0 2 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2308 3.6974 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7473 3.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5398 4.6485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0563 2.5385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2942 -2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 31 1 0 0 0 0 3 31 1 0 0 0 0 4 32 1 0 0 0 0 5 32 1 0 0 0 0 6 33 1 0 0 0 0 8 35 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 35 1 0 0 0 0 16 23 1 0 0 0 0 16 27 1 0 0 0 0 17 24 1 0 0 0 0 17 34 1 0 0 0 0 18 28 1 0 0 0 0 18 33 1 0 0 0 0 19 29 1 0 0 0 0 19 33 1 0 0 0 0 20 1 1 1 0 0 0 20 21 1 0 0 0 0 21 36 1 1 0 0 0 22 23 2 0 0 0 0 22 35 1 0 0 0 0 23 34 1 0 0 0 0 24 30 1 0 0 0 0 24 45 1 6 0 0 0 25 31 1 0 0 0 0 25 34 1 1 0 0 0 26 32 1 0 0 0 0 26 37 1 6 0 0 0 27 36 1 6 0 0 0 27 38 1 0 0 0 0 28 39 2 0 0 0 0 28 40 1 0 0 0 0 29 41 2 0 0 0 0 29 45 1 0 0 0 0 30 31 1 0 0 0 0 30 42 1 1 0 0 0 32 43 1 0 0 0 0 33 44 1 0 0 0 0 34 7 1 1 0 0 0 35 36 1 6 0 0 0 36 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	636.42
Volume:	668.189
LogP:	3.994
LogD:	3.014
LogS:	-3.603
# Rotatable Bonds:	11
TPSA:	164.75
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.147
Synthetic Accessibility Score:	5.519
Fsp3:	0.889
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:	-5.566
MDCK Permeability:	4.721302047983045e-06
Pgp-inhibitor:	0.318
Pgp-substrate:	0.145
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.176
30% Bioavailability (F30%):	0.383

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	86.88895416259766%
Volume Distribution (VD):	0.445
Pgp-substrate:	5.346335411071777%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.08
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.758
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.085
CYP3A4-substrate:	0.32

ADMET: Excretion

Clearance (CL):	2.415
Half-life (T1/2):	0.698

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.324
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.687
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.281
Carcinogencity:	0.016
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC471119

Natural Product ID:	NPC471119
*Common Name:**	Fasciculic Acid B
IUPAC Name:	5-[[(2R,3R,5R,10S,12S,13R,14S,17R)-17-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-3,12-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl]oxy]-3-hydroxy-3-methyl-5-oxopentanoic acid
Synonyms:
Standard InCHIKey:	SWRXIGFQDQTNKP-PEEMPJFVSA-N
Standard InCHI:	InChI=1S/C36H60O9/c1-20(10-13-26(37)32(4,5)43)21-14-15-35(8)22-11-12-25-31(2,3)30(42)24(45-29(41)19-33(6,44)18-28(39)40)17-34(25,7)23(22)16-27(38)36(21,35)9/h20-21,24-27,30,37-38,42-44H,10-19H2,1-9H3,(H,39,40)/t20-,21-,24-,25+,26-,27+,30+,33?,34-,35+,36+/m1/s1
SMILES:	CC(CCC(C(C)(C)O)O)C1CCC2(C1(C(CC3=C2CCC4C3(CC(C(C4(C)C)O)OC(=O)CC(C)(CC(=O)O)O)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375636
PubChem CID:	14506483
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO33351	naematoloma fasciculare	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23634786]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	93100.0	nM	PMID[525486]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	28480.0	nM	PMID[525486]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	27200.0	nM	PMID[525486]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	22170.0	nM	PMID[525486]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	16600.0	nM	PMID[525486]

☑ 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 NPC471119 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	221
0.1-0.2	1502
0.2-0.3	5114
0.3-0.4	12012
0.4-0.5	9814
0.5-0.6	6405
0.6-0.7	6314
0.7-0.8	1273
0.8-0.85	26
0.85-0.9	8
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC296879
0.9895	High Similarity	NPC55954
0.9895	High Similarity	NPC218513
0.9307	High Similarity	NPC90630
0.9307	High Similarity	NPC475243
0.9184	High Similarity	NPC475558
0.9184	High Similarity	NPC473788
0.902	High Similarity	NPC475364
0.8611	High Similarity	NPC471117
0.8611	High Similarity	NPC471120
0.8598	High Similarity	NPC116024
0.8544	High Similarity	NPC475494
0.8542	High Similarity	NPC473269
0.8532	High Similarity	NPC471118
0.8532	High Similarity	NPC471121
0.8485	Intermediate Similarity	NPC120708
0.8476	Intermediate Similarity	NPC477070
0.8476	Intermediate Similarity	NPC477069
0.8318	Intermediate Similarity	NPC477073
0.8302	Intermediate Similarity	NPC218853
0.8241	Intermediate Similarity	NPC280782
0.8224	Intermediate Similarity	NPC250956
0.8208	Intermediate Similarity	NPC195708
0.82	Intermediate Similarity	NPC469329
0.82	Intermediate Similarity	NPC473648
0.82	Intermediate Similarity	NPC30677
0.82	Intermediate Similarity	NPC180557
0.82	Intermediate Similarity	NPC37787
0.82	Intermediate Similarity	NPC473415
0.819	Intermediate Similarity	NPC472655
0.8182	Intermediate Similarity	NPC27918
0.8173	Intermediate Similarity	NPC474124
0.8165	Intermediate Similarity	NPC477074
0.8163	Intermediate Similarity	NPC136801
0.8155	Intermediate Similarity	NPC289670
0.8148	Intermediate Similarity	NPC472003
0.8131	Intermediate Similarity	NPC265655
0.81	Intermediate Similarity	NPC240617
0.8095	Intermediate Similarity	NPC475036
0.8095	Intermediate Similarity	NPC473543
0.8095	Intermediate Similarity	NPC471293
0.8081	Intermediate Similarity	NPC26888
0.8077	Intermediate Similarity	NPC475344
0.8077	Intermediate Similarity	NPC476471
0.8073	Intermediate Similarity	NPC233003
0.8061	Intermediate Similarity	NPC474889
0.8058	Intermediate Similarity	NPC167974
0.8058	Intermediate Similarity	NPC316964
0.8058	Intermediate Similarity	NPC473510
0.8058	Intermediate Similarity	NPC230546
0.8056	Intermediate Similarity	NPC129340
0.8041	Intermediate Similarity	NPC138756
0.8039	Intermediate Similarity	NPC475033
0.8039	Intermediate Similarity	NPC475032
0.8037	Intermediate Similarity	NPC472218
0.8037	Intermediate Similarity	NPC472219
0.8037	Intermediate Similarity	NPC472217
0.8037	Intermediate Similarity	NPC258323
0.802	Intermediate Similarity	NPC200702
0.8019	Intermediate Similarity	NPC470587
0.8	Intermediate Similarity	NPC473523
0.8	Intermediate Similarity	NPC251309
0.7982	Intermediate Similarity	NPC285410
0.7982	Intermediate Similarity	NPC250481
0.7982	Intermediate Similarity	NPC292196
0.7982	Intermediate Similarity	NPC263827
0.7981	Intermediate Similarity	NPC473514
0.7981	Intermediate Similarity	NPC476132
0.7981	Intermediate Similarity	NPC155974
0.7981	Intermediate Similarity	NPC475617
0.798	Intermediate Similarity	NPC20388
0.798	Intermediate Similarity	NPC111585
0.798	Intermediate Similarity	NPC175628
0.798	Intermediate Similarity	NPC289213
0.798	Intermediate Similarity	NPC148414
0.7965	Intermediate Similarity	NPC472933
0.7963	Intermediate Similarity	NPC472216
0.7963	Intermediate Similarity	NPC5475
0.7963	Intermediate Similarity	NPC284828
0.7963	Intermediate Similarity	NPC173905
0.7961	Intermediate Similarity	NPC470068
0.7961	Intermediate Similarity	NPC470067
0.7961	Intermediate Similarity	NPC119036
0.7961	Intermediate Similarity	NPC102426
0.7961	Intermediate Similarity	NPC470066
0.7961	Intermediate Similarity	NPC300179
0.7959	Intermediate Similarity	NPC242864
0.7946	Intermediate Similarity	NPC472934
0.7944	Intermediate Similarity	NPC59530
0.7941	Intermediate Similarity	NPC471777
0.7941	Intermediate Similarity	NPC471822
0.7928	Intermediate Similarity	NPC220293
0.7925	Intermediate Similarity	NPC96268
0.7925	Intermediate Similarity	NPC216245
0.7925	Intermediate Similarity	NPC65523
0.7925	Intermediate Similarity	NPC135854
0.7925	Intermediate Similarity	NPC470251
0.7925	Intermediate Similarity	NPC2436
0.7921	Intermediate Similarity	NPC474922
0.7909	Intermediate Similarity	NPC152117
0.7909	Intermediate Similarity	NPC234042
0.7905	Intermediate Similarity	NPC470053
0.7905	Intermediate Similarity	NPC473928
0.7905	Intermediate Similarity	NPC469316
0.79	Intermediate Similarity	NPC189520
0.79	Intermediate Similarity	NPC473166
0.7895	Intermediate Similarity	NPC251226
0.7895	Intermediate Similarity	NPC7988
0.789	Intermediate Similarity	NPC5284
0.789	Intermediate Similarity	NPC129689
0.789	Intermediate Similarity	NPC101450
0.7885	Intermediate Similarity	NPC476195
0.7885	Intermediate Similarity	NPC208358
0.7872	Intermediate Similarity	NPC22403
0.787	Intermediate Similarity	NPC273155
0.7864	Intermediate Similarity	NPC210337
0.7857	Intermediate Similarity	NPC16081
0.7857	Intermediate Similarity	NPC173686
0.785	Intermediate Similarity	NPC60315
0.785	Intermediate Similarity	NPC477877
0.785	Intermediate Similarity	NPC323834
0.7843	Intermediate Similarity	NPC470016
0.7843	Intermediate Similarity	NPC69548
0.7843	Intermediate Similarity	NPC184848
0.7843	Intermediate Similarity	NPC48330
0.7843	Intermediate Similarity	NPC279974
0.7843	Intermediate Similarity	NPC317586
0.7838	Intermediate Similarity	NPC194273
0.7838	Intermediate Similarity	NPC320118
0.7838	Intermediate Similarity	NPC472926
0.783	Intermediate Similarity	NPC473694
0.783	Intermediate Similarity	NPC475623
0.783	Intermediate Similarity	NPC33973
0.783	Intermediate Similarity	NPC70967
0.783	Intermediate Similarity	NPC159442
0.783	Intermediate Similarity	NPC475334
0.7826	Intermediate Similarity	NPC4021
0.7826	Intermediate Similarity	NPC129434
0.7826	Intermediate Similarity	NPC159456
0.7818	Intermediate Similarity	NPC115303
0.7812	Intermediate Similarity	NPC132635
0.781	Intermediate Similarity	NPC470054
0.781	Intermediate Similarity	NPC469327
0.7807	Intermediate Similarity	NPC230513
0.7807	Intermediate Similarity	NPC42673
0.7807	Intermediate Similarity	NPC232258
0.78	Intermediate Similarity	NPC471896
0.78	Intermediate Similarity	NPC469400
0.7798	Intermediate Similarity	NPC286174
0.7798	Intermediate Similarity	NPC41405
0.7798	Intermediate Similarity	NPC77947
0.7798	Intermediate Similarity	NPC118225
0.7788	Intermediate Similarity	NPC472927
0.7788	Intermediate Similarity	NPC55296
0.7788	Intermediate Similarity	NPC477252
0.7788	Intermediate Similarity	NPC470171
0.7778	Intermediate Similarity	NPC469318
0.7778	Intermediate Similarity	NPC166993
0.7778	Intermediate Similarity	NPC130229
0.7778	Intermediate Similarity	NPC473173
0.7778	Intermediate Similarity	NPC9457
0.7778	Intermediate Similarity	NPC471783
0.7778	Intermediate Similarity	NPC112780
0.7768	Intermediate Similarity	NPC323821
0.7768	Intermediate Similarity	NPC243354
0.7768	Intermediate Similarity	NPC45218
0.7768	Intermediate Similarity	NPC268238
0.7768	Intermediate Similarity	NPC473882
0.7768	Intermediate Similarity	NPC473898
0.7768	Intermediate Similarity	NPC143268
0.7768	Intermediate Similarity	NPC284915
0.7767	Intermediate Similarity	NPC327788
0.7767	Intermediate Similarity	NPC471903
0.7767	Intermediate Similarity	NPC88009
0.7767	Intermediate Similarity	NPC173272
0.7767	Intermediate Similarity	NPC129569
0.7767	Intermediate Similarity	NPC42042
0.7767	Intermediate Similarity	NPC7124
0.7759	Intermediate Similarity	NPC269642
0.7757	Intermediate Similarity	NPC31430
0.7757	Intermediate Similarity	NPC223741
0.7757	Intermediate Similarity	NPC181104
0.7757	Intermediate Similarity	NPC474550
0.7757	Intermediate Similarity	NPC473577
0.7757	Intermediate Similarity	NPC288502
0.7757	Intermediate Similarity	NPC103298
0.7757	Intermediate Similarity	NPC80809
0.7757	Intermediate Similarity	NPC85593
0.7757	Intermediate Similarity	NPC475331
0.7757	Intermediate Similarity	NPC475335
0.7757	Intermediate Similarity	NPC201144
0.7757	Intermediate Similarity	NPC475585
0.7757	Intermediate Similarity	NPC121518
0.7755	Intermediate Similarity	NPC28252
0.7755	Intermediate Similarity	NPC55309
0.7755	Intermediate Similarity	NPC474970
0.7748	Intermediate Similarity	NPC477253
0.7745	Intermediate Similarity	NPC318332
0.7745	Intermediate Similarity	NPC166906
0.7739	Intermediate Similarity	NPC471406

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 NPC471119 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	2026
0.2-0.3	3953
0.3-0.4	1999
0.4-0.5	505
0.5-0.6	241
0.6-0.7	210
0.7-0.8	18
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7636	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD8297	Approved
0.7586	Intermediate Similarity	NPD6319	Approved
0.7478	Intermediate Similarity	NPD7115	Discovery
0.7478	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD6402	Approved
0.7364	Intermediate Similarity	NPD5739	Approved
0.7364	Intermediate Similarity	NPD7128	Approved
0.7364	Intermediate Similarity	NPD6675	Approved
0.7321	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6372	Approved
0.7321	Intermediate Similarity	NPD6373	Approved
0.7308	Intermediate Similarity	NPD6399	Phase 3
0.729	Intermediate Similarity	NPD7638	Approved
0.7232	Intermediate Similarity	NPD6881	Approved
0.7232	Intermediate Similarity	NPD7320	Approved
0.7232	Intermediate Similarity	NPD6899	Approved
0.7222	Intermediate Similarity	NPD7640	Approved
0.7222	Intermediate Similarity	NPD7639	Approved
0.7217	Intermediate Similarity	NPD4632	Approved
0.7213	Intermediate Similarity	NPD8293	Discontinued
0.7212	Intermediate Similarity	NPD6411	Approved
0.7193	Intermediate Similarity	NPD6649	Approved
0.7193	Intermediate Similarity	NPD8130	Phase 1
0.7193	Intermediate Similarity	NPD6650	Approved
0.719	Intermediate Similarity	NPD7492	Approved
0.7154	Intermediate Similarity	NPD7736	Approved
0.7143	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD6059	Approved
0.7143	Intermediate Similarity	NPD5701	Approved
0.7143	Intermediate Similarity	NPD5697	Approved
0.7131	Intermediate Similarity	NPD6616	Approved
0.713	Intermediate Similarity	NPD6882	Approved
0.713	Intermediate Similarity	NPD4225	Approved
0.7105	Intermediate Similarity	NPD6883	Approved
0.7105	Intermediate Similarity	NPD7290	Approved
0.7105	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7102	Approved
0.7097	Intermediate Similarity	NPD7319	Approved
0.7091	Intermediate Similarity	NPD7632	Discontinued
0.708	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7078	Approved
0.7048	Intermediate Similarity	NPD8034	Phase 2
0.7048	Intermediate Similarity	NPD8035	Phase 2
0.7043	Intermediate Similarity	NPD6869	Approved
0.7043	Intermediate Similarity	NPD6847	Approved
0.7043	Intermediate Similarity	NPD6617	Approved
0.7037	Intermediate Similarity	NPD6083	Phase 2
0.7037	Intermediate Similarity	NPD6084	Phase 2
0.703	Intermediate Similarity	NPD4786	Approved
0.7025	Intermediate Similarity	NPD6370	Approved
0.7019	Intermediate Similarity	NPD5328	Approved
0.7019	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6101	Approved
0.7018	Intermediate Similarity	NPD6012	Approved
0.7018	Intermediate Similarity	NPD6013	Approved
0.7018	Intermediate Similarity	NPD6014	Approved
0.7009	Intermediate Similarity	NPD5695	Phase 3
0.6992	Remote Similarity	NPD7507	Approved
0.6967	Remote Similarity	NPD8328	Phase 3
0.6961	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4634	Approved
0.6942	Remote Similarity	NPD8033	Approved
0.6942	Remote Similarity	NPD6015	Approved
0.6942	Remote Similarity	NPD6016	Approved
0.693	Remote Similarity	NPD6011	Approved
0.6923	Remote Similarity	NPD8133	Approved
0.6917	Remote Similarity	NPD7516	Approved
0.6916	Remote Similarity	NPD7748	Approved
0.6903	Remote Similarity	NPD6008	Approved
0.6897	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6009	Approved
0.6887	Remote Similarity	NPD6079	Approved
0.6887	Remote Similarity	NPD7637	Suspended
0.6885	Remote Similarity	NPD5988	Approved
0.6881	Remote Similarity	NPD4755	Approved
0.686	Remote Similarity	NPD8377	Approved
0.686	Remote Similarity	NPD8294	Approved
0.6842	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6412	Phase 2
0.6833	Remote Similarity	NPD7328	Approved
0.6833	Remote Similarity	NPD7327	Approved
0.6832	Remote Similarity	NPD3667	Approved
0.6829	Remote Similarity	NPD7604	Phase 2
0.6827	Remote Similarity	NPD7524	Approved
0.6822	Remote Similarity	NPD5779	Approved
0.6822	Remote Similarity	NPD5778	Approved
0.6818	Remote Similarity	NPD5696	Approved
0.6803	Remote Similarity	NPD5983	Phase 2
0.6803	Remote Similarity	NPD8296	Approved
0.6803	Remote Similarity	NPD8379	Approved
0.6803	Remote Similarity	NPD8335	Approved
0.6803	Remote Similarity	NPD8380	Approved
0.6803	Remote Similarity	NPD8378	Approved
0.68	Remote Similarity	NPD4748	Discontinued
0.68	Remote Similarity	NPD7525	Registered
0.6768	Remote Similarity	NPD6115	Approved
0.6768	Remote Similarity	NPD6697	Approved
0.6768	Remote Similarity	NPD6118	Approved
0.6768	Remote Similarity	NPD6114	Approved
0.6757	Remote Similarity	NPD4700	Approved
0.6757	Remote Similarity	NPD5286	Approved
0.6757	Remote Similarity	NPD4696	Approved
0.6757	Remote Similarity	NPD5285	Approved
0.6735	Remote Similarity	NPD6117	Approved
0.6731	Remote Similarity	NPD3618	Phase 1
0.6729	Remote Similarity	NPD7515	Phase 2
0.6727	Remote Similarity	NPD7902	Approved
0.672	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD6116	Phase 1
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6639	Remote Similarity	NPD7101	Approved
0.6639	Remote Similarity	NPD7100	Approved
0.6638	Remote Similarity	NPD6686	Approved
0.6637	Remote Similarity	NPD4633	Approved
0.6637	Remote Similarity	NPD5224	Approved
0.6637	Remote Similarity	NPD5226	Approved
0.6637	Remote Similarity	NPD5211	Phase 2
0.6637	Remote Similarity	NPD5225	Approved
0.6636	Remote Similarity	NPD5221	Approved
0.6636	Remote Similarity	NPD5222	Approved
0.6636	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4697	Phase 3
0.6633	Remote Similarity	NPD7339	Approved
0.6633	Remote Similarity	NPD6942	Approved
0.6614	Remote Similarity	NPD6033	Approved
0.6609	Remote Similarity	NPD4768	Approved
0.6609	Remote Similarity	NPD4767	Approved
0.6604	Remote Similarity	NPD6672	Approved
0.6604	Remote Similarity	NPD5737	Approved
0.6579	Remote Similarity	NPD5174	Approved
0.6579	Remote Similarity	NPD5175	Approved
0.6577	Remote Similarity	NPD5173	Approved
0.6574	Remote Similarity	NPD7983	Approved
0.6571	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6684	Approved
0.6571	Remote Similarity	NPD7334	Approved
0.6571	Remote Similarity	NPD6409	Approved
0.6571	Remote Similarity	NPD7146	Approved
0.6571	Remote Similarity	NPD5330	Approved
0.6571	Remote Similarity	NPD7521	Approved
0.6557	Remote Similarity	NPD6335	Approved
0.6555	Remote Similarity	NPD6053	Discontinued
0.6549	Remote Similarity	NPD5223	Approved
0.6549	Remote Similarity	NPD4159	Approved
0.6545	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4753	Phase 2
0.6532	Remote Similarity	NPD6909	Approved
0.6532	Remote Similarity	NPD6908	Approved
0.6532	Remote Similarity	NPD6921	Approved
0.6531	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6868	Approved
0.6522	Remote Similarity	NPD5141	Approved
0.6496	Remote Similarity	NPD4730	Approved
0.6496	Remote Similarity	NPD4729	Approved
0.6475	Remote Similarity	NPD6317	Approved
0.6458	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7900	Approved
0.6449	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6903	Approved
0.6442	Remote Similarity	NPD6695	Phase 3
0.6435	Remote Similarity	NPD4754	Approved
0.6423	Remote Similarity	NPD6313	Approved
0.6423	Remote Similarity	NPD6314	Approved
0.6422	Remote Similarity	NPD5284	Approved
0.6422	Remote Similarity	NPD6050	Approved
0.6422	Remote Similarity	NPD5281	Approved
0.6415	Remote Similarity	NPD6098	Approved
0.6415	Remote Similarity	NPD5279	Phase 3
0.6408	Remote Similarity	NPD4692	Approved
0.6408	Remote Similarity	NPD4139	Approved
0.6406	Remote Similarity	NPD8074	Phase 3
0.6404	Remote Similarity	NPD5344	Discontinued
0.6404	Remote Similarity	NPD1700	Approved
0.64	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6933	Approved
0.6396	Remote Similarity	NPD5210	Approved
0.6396	Remote Similarity	NPD4629	Approved
0.6389	Remote Similarity	NPD6051	Approved
0.6389	Remote Similarity	NPD6080	Approved
0.6389	Remote Similarity	NPD6904	Approved
0.6389	Remote Similarity	NPD6673	Approved
0.6387	Remote Similarity	NPD5249	Phase 3
0.6387	Remote Similarity	NPD5247	Approved
0.6387	Remote Similarity	NPD5248	Approved
0.6387	Remote Similarity	NPD5250	Approved
0.6387	Remote Similarity	NPD5251	Approved
0.6381	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD3668	Phase 3
0.6381	Remote Similarity	NPD3666	Approved
0.6381	Remote Similarity	NPD3133	Approved
0.6381	Remote Similarity	NPD3665	Phase 1
0.6379	Remote Similarity	NPD8170	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