NPASS Compound

Structure

NPC476471 OpenBabel07101718292D 41 44 0 0 1 0 0 0 0 0999 V2000 5.7633 5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1161 6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4762 4.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1453 3.9190 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 -0.8660 0.5000 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7852 5.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 2.7601 0.0000 C 0 0 1 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 1.7321 -3.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8363 2.9680 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5054 2.2248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 14 32 1 0 0 0 0 15 22 2 0 0 0 0 15 28 1 0 0 0 0 16 26 1 0 0 0 0 16 33 1 0 0 0 0 18 3 1 6 0 0 0 18 23 1 0 0 0 0 18 25 1 0 0 0 0 19 34 2 0 0 0 0 19 39 1 0 0 0 0 20 35 2 0 0 0 0 20 40 1 0 0 0 0 21 36 2 0 0 0 0 21 41 1 0 0 0 0 22 24 1 0 0 0 0 22 29 1 0 0 0 0 23 33 1 1 0 0 0 24 33 1 1 0 0 0 25 37 1 1 0 0 0 26 29 1 0 0 0 0 26 38 1 6 0 0 0 27 31 1 0 0 0 0 27 39 1 1 0 0 0 28 30 1 0 0 0 0 28 40 1 6 0 0 0 29 32 1 1 0 0 0 30 31 1 0 0 0 0 30 32 1 1 0 0 0 31 41 1 1 0 0 0 32 7 1 1 0 0 0 33 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.37
Volume:	604.874
LogP:	4.721
LogD:	4.242
LogS:	-4.284
# Rotatable Bonds:	11
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.236
Synthetic Accessibility Score:	5.302
Fsp3:	0.848
Lipinski Rule-of-5:	Accepted
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:	-4.762
MDCK Permeability:	9.186266834149137e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.989
Human Intestinal Absorption (HIA):	0.478
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.758

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	86.27295684814453%
Volume Distribution (VD):	1.892
Pgp-substrate:	3.4343104362487793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.397
CYP2C9-inhibitor:	0.229
CYP2C9-substrate:	0.102
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.595
CYP3A4-substrate:	0.382

ADMET: Excretion

Clearance (CL):	2.287
Half-life (T1/2):	0.518

ADMET: Toxicity

hERG Blockers:	0.094
Human Hepatotoxicity (H-HT):	0.961
Drug-inuced Liver Injury (DILI):	0.893
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.178
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.111
Carcinogencity:	0.014
Eye Corrosion:	0.014
Eye Irritation:	0.039
Respiratory Toxicity:	0.871

Download Data

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

Natural Product: NPC476471

Natural Product ID:	NPC476471
*Common Name:**	Agosterol A
IUPAC Name:	[(3S,4R,5S,6S,9R,10R,11R,13R,14R,17R)-4,6-diacetyloxy-11-hydroxy-17-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Synonyms:
Standard InCHIKey:	SUIRSZOPEPPNGJ-JGEDILIOSA-N
Standard InCHI:	InChI=1S/C33H52O8/c1-17(2)9-12-25(37)18(3)23-10-11-24-22-15-28(40-20(5)35)30-31(41-21(6)36)27(39-19(4)34)13-14-32(30,7)29(22)26(38)16-33(23,24)8/h15,17-18,23-31,37-38H,9-14,16H2,1-8H3/t18-,23+,24-,25+,26+,27-,28-,29+,30-,31-,32+,33+/m0/s1
SMILES:	CC(C)CCC(C(C)C1CCC2C1(CC(C3C2=CC(C4C3(CCC(C4OC(=O)C)OC(=O)C)C)OC(=O)C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL82446
PubChem CID:	10348156
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0001104] Trihydroxy bile acids, alcohols and derivatives

*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
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510593]
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	Indonesia	n.a.	PMID[15568767]
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18257533]
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834155]

☑ 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	2
Others	8

Activity Type	# Activity
Cell Line	8
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1178	Cell Line	KB 3-1	Homo sapiens	Inhibition	=	13.0	%	PMID[479511]
NPT1178	Cell Line	KB 3-1	Homo sapiens	Inhibition	=	84.0	%	PMID[479511]
NPT1178	Cell Line	KB 3-1	Homo sapiens	Inhibition	=	82.0	%	PMID[479511]
NPT1178	Cell Line	KB 3-1	Homo sapiens	Inhibition	=	75.0	%	PMID[479511]
NPT1178	Cell Line	KB 3-1	Homo sapiens	Inhibition	=	76.0	%	PMID[479511]
NPT1178	Cell Line	KB 3-1	Homo sapiens	Inhibition	=	73.0	%	PMID[479511]
NPT1178	Cell Line	KB 3-1	Homo sapiens	Inhibition	=	66.0	%	PMID[479511]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	25.0	ug.mL-1	PMID[479512]
NPT2850	Individual Protein	Multidrug resistance associated protein	Homo sapiens	Activity	=	56.9	%	PMID[479513]
NPT2	Others	Unspecified		IC50	=	50.0	ug.mL-1	PMID[479512]

☑ 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 NPC476471 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	197
0.1-0.2	1308
0.2-0.3	4213
0.3-0.4	8707
0.4-0.5	12438
0.5-0.6	6243
0.6-0.7	5589
0.7-0.8	3605
0.8-0.85	349
0.85-0.9	37
0.9-0.95	5
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475344
0.9895	High Similarity	NPC474124
0.9792	High Similarity	NPC473543
0.9688	High Similarity	NPC473523
0.9684	High Similarity	NPC475617
0.9375	High Similarity	NPC230546
0.9375	High Similarity	NPC473510
0.9263	High Similarity	NPC88009
0.9167	High Similarity	NPC210337
0.9043	High Similarity	NPC234335
0.8969	High Similarity	NPC475033
0.8969	High Similarity	NPC475032
0.8889	High Similarity	NPC155974
0.8866	High Similarity	NPC276103
0.8866	High Similarity	NPC54248
0.8854	High Similarity	NPC474922
0.8835	High Similarity	NPC5475
0.8835	High Similarity	NPC173905
0.8835	High Similarity	NPC472216
0.8835	High Similarity	NPC284828
0.8824	High Similarity	NPC473586
0.8812	High Similarity	NPC474550
0.8812	High Similarity	NPC473577
0.8812	High Similarity	NPC475585
0.8788	High Similarity	NPC208358
0.875	High Similarity	NPC472214
0.875	High Similarity	NPC472215
0.8738	High Similarity	NPC88701
0.8738	High Similarity	NPC475263
0.8725	High Similarity	NPC475290
0.87	High Similarity	NPC472554
0.8687	High Similarity	NPC102426
0.8687	High Similarity	NPC300179
0.8673	High Similarity	NPC471765
0.8673	High Similarity	NPC98457
0.8673	High Similarity	NPC221801
0.8673	High Similarity	NPC475178
0.8673	High Similarity	NPC211810
0.8673	High Similarity	NPC227583
0.8673	High Similarity	NPC284194
0.8673	High Similarity	NPC12103
0.8673	High Similarity	NPC253115
0.8673	High Similarity	NPC304899
0.866	High Similarity	NPC105375
0.866	High Similarity	NPC472360
0.866	High Similarity	NPC472416
0.866	High Similarity	NPC182826
0.8641	High Similarity	NPC475781
0.8632	High Similarity	NPC246028
0.8627	High Similarity	NPC93352
0.8614	High Similarity	NPC472552
0.8586	High Similarity	NPC473244
0.8586	High Similarity	NPC274793
0.8571	High Similarity	NPC8774
0.8558	High Similarity	NPC472219
0.8558	High Similarity	NPC472218
0.8558	High Similarity	NPC472217
0.8544	High Similarity	NPC119855
0.8544	High Similarity	NPC88349
0.8544	High Similarity	NPC220217
0.8529	High Similarity	NPC281378
0.8529	High Similarity	NPC473694
0.8529	High Similarity	NPC475334
0.8529	High Similarity	NPC475623
0.8519	High Similarity	NPC207637
0.8515	High Similarity	NPC96784
0.8515	High Similarity	NPC289670
0.8515	High Similarity	NPC476132
0.8515	High Similarity	NPC11974
0.8515	High Similarity	NPC235920
0.8511	High Similarity	NPC474970
0.85	High Similarity	NPC470066
0.85	High Similarity	NPC247233
0.85	High Similarity	NPC470067
0.85	High Similarity	NPC470068
0.8491	Intermediate Similarity	NPC470076
0.8485	Intermediate Similarity	NPC288970
0.8485	Intermediate Similarity	NPC72204
0.8485	Intermediate Similarity	NPC471903
0.8485	Intermediate Similarity	NPC129569
0.8476	Intermediate Similarity	NPC40728
0.8469	Intermediate Similarity	NPC65402
0.8469	Intermediate Similarity	NPC127718
0.8462	Intermediate Similarity	NPC33053
0.8462	Intermediate Similarity	NPC471205
0.8454	Intermediate Similarity	NPC177641
0.8447	Intermediate Similarity	NPC85593
0.8447	Intermediate Similarity	NPC75608
0.8447	Intermediate Similarity	NPC80809
0.8447	Intermediate Similarity	NPC121518
0.8447	Intermediate Similarity	NPC201144
0.8447	Intermediate Similarity	NPC103298
0.8447	Intermediate Similarity	NPC31430
0.8447	Intermediate Similarity	NPC288502
0.8447	Intermediate Similarity	NPC475331
0.8447	Intermediate Similarity	NPC475335
0.8447	Intermediate Similarity	NPC152966
0.8447	Intermediate Similarity	NPC181104
0.844	Intermediate Similarity	NPC203862
0.8438	Intermediate Similarity	NPC473647
0.8438	Intermediate Similarity	NPC261320
0.8431	Intermediate Similarity	NPC470053
0.8431	Intermediate Similarity	NPC470972
0.8416	Intermediate Similarity	NPC477972
0.8416	Intermediate Similarity	NPC477968
0.8416	Intermediate Similarity	NPC476195
0.8416	Intermediate Similarity	NPC228251
0.8416	Intermediate Similarity	NPC161527
0.8416	Intermediate Similarity	NPC20113
0.8416	Intermediate Similarity	NPC474190
0.8416	Intermediate Similarity	NPC38855
0.8416	Intermediate Similarity	NPC477971
0.8416	Intermediate Similarity	NPC188968
0.8416	Intermediate Similarity	NPC219285
0.8396	Intermediate Similarity	NPC475563
0.8396	Intermediate Similarity	NPC475134
0.8396	Intermediate Similarity	NPC177047
0.8384	Intermediate Similarity	NPC241047
0.8384	Intermediate Similarity	NPC276110
0.8381	Intermediate Similarity	NPC128795
0.8381	Intermediate Similarity	NPC48548
0.8381	Intermediate Similarity	NPC50124
0.8381	Intermediate Similarity	NPC135015
0.8381	Intermediate Similarity	NPC217921
0.8367	Intermediate Similarity	NPC473678
0.8365	Intermediate Similarity	NPC186668
0.8365	Intermediate Similarity	NPC60315
0.8365	Intermediate Similarity	NPC473199
0.8365	Intermediate Similarity	NPC51719
0.8365	Intermediate Similarity	NPC471206
0.8351	Intermediate Similarity	NPC295668
0.8351	Intermediate Similarity	NPC220216
0.835	Intermediate Similarity	NPC36688
0.835	Intermediate Similarity	NPC189588
0.835	Intermediate Similarity	NPC10232
0.835	Intermediate Similarity	NPC187302
0.835	Intermediate Similarity	NPC472821
0.835	Intermediate Similarity	NPC97487
0.835	Intermediate Similarity	NPC196471
0.835	Intermediate Similarity	NPC160583
0.8349	Intermediate Similarity	NPC470075
0.8349	Intermediate Similarity	NPC146652
0.8333	Intermediate Similarity	NPC470054
0.8333	Intermediate Similarity	NPC222875
0.8333	Intermediate Similarity	NPC268829
0.8333	Intermediate Similarity	NPC295110
0.8333	Intermediate Similarity	NPC470612
0.8333	Intermediate Similarity	NPC49532
0.8333	Intermediate Similarity	NPC247701
0.8333	Intermediate Similarity	NPC470613
0.8333	Intermediate Similarity	NPC473160
0.8333	Intermediate Similarity	NPC144068
0.8333	Intermediate Similarity	NPC25177
0.8318	Intermediate Similarity	NPC17791
0.8318	Intermediate Similarity	NPC263827
0.8318	Intermediate Similarity	NPC250481
0.8318	Intermediate Similarity	NPC285410
0.8318	Intermediate Similarity	NPC475668
0.8318	Intermediate Similarity	NPC114188
0.8318	Intermediate Similarity	NPC475480
0.8318	Intermediate Similarity	NPC473921
0.8317	Intermediate Similarity	NPC477875
0.8317	Intermediate Similarity	NPC477876
0.8302	Intermediate Similarity	NPC316974
0.8302	Intermediate Similarity	NPC43976
0.8302	Intermediate Similarity	NPC14630
0.8302	Intermediate Similarity	NPC51925
0.8302	Intermediate Similarity	NPC472901
0.8302	Intermediate Similarity	NPC250089
0.8302	Intermediate Similarity	NPC475586
0.8302	Intermediate Similarity	NPC154085
0.8302	Intermediate Similarity	NPC157530
0.8302	Intermediate Similarity	NPC296761
0.8302	Intermediate Similarity	NPC125361
0.83	Intermediate Similarity	NPC475304
0.83	Intermediate Similarity	NPC306797
0.83	Intermediate Similarity	NPC169270
0.83	Intermediate Similarity	NPC292718
0.83	Intermediate Similarity	NPC111834
0.8288	Intermediate Similarity	NPC304260
0.8288	Intermediate Similarity	NPC44899
0.8288	Intermediate Similarity	NPC29639
0.8288	Intermediate Similarity	NPC5883
0.8288	Intermediate Similarity	NPC477071
0.8286	Intermediate Similarity	NPC88013
0.8286	Intermediate Similarity	NPC472390
0.8286	Intermediate Similarity	NPC125423
0.8286	Intermediate Similarity	NPC234160
0.8283	Intermediate Similarity	NPC105490
0.8283	Intermediate Similarity	NPC3359
0.8273	Intermediate Similarity	NPC93883
0.8273	Intermediate Similarity	NPC152615
0.8269	Intermediate Similarity	NPC470768
0.8265	Intermediate Similarity	NPC219516
0.8265	Intermediate Similarity	NPC477574
0.8265	Intermediate Similarity	NPC124374
0.8265	Intermediate Similarity	NPC210268
0.8265	Intermediate Similarity	NPC130840
0.8252	Intermediate Similarity	NPC258547
0.8252	Intermediate Similarity	NPC283343

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 NPC476471 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1472
0.2-0.3	3829
0.3-0.4	2428
0.4-0.5	731
0.5-0.6	244
0.6-0.7	205
0.7-0.8	78
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8317	Intermediate Similarity	NPD7638	Approved
0.8235	Intermediate Similarity	NPD7639	Approved
0.8235	Intermediate Similarity	NPD7640	Approved
0.8142	Intermediate Similarity	NPD8033	Approved
0.8125	Intermediate Similarity	NPD7516	Approved
0.8053	Intermediate Similarity	NPD8294	Approved
0.8053	Intermediate Similarity	NPD8377	Approved
0.8036	Intermediate Similarity	NPD7328	Approved
0.8036	Intermediate Similarity	NPD7327	Approved
0.7982	Intermediate Similarity	NPD8379	Approved
0.7982	Intermediate Similarity	NPD8335	Approved
0.7982	Intermediate Similarity	NPD8378	Approved
0.7982	Intermediate Similarity	NPD8296	Approved
0.7982	Intermediate Similarity	NPD8380	Approved
0.7826	Intermediate Similarity	NPD7503	Approved
0.7647	Intermediate Similarity	NPD6399	Phase 3
0.7636	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7115	Discovery
0.7619	Intermediate Similarity	NPD4225	Approved
0.7589	Intermediate Similarity	NPD8297	Approved
0.757	Intermediate Similarity	NPD7632	Discontinued
0.7568	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD7507	Approved
0.7545	Intermediate Similarity	NPD6686	Approved
0.7525	Intermediate Similarity	NPD6051	Approved
0.75	Intermediate Similarity	NPD7525	Registered
0.75	Intermediate Similarity	NPD7524	Approved
0.7477	Intermediate Similarity	NPD5344	Discontinued
0.7379	Intermediate Similarity	NPD7637	Suspended
0.7377	Intermediate Similarity	NPD7319	Approved
0.7374	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8133	Approved
0.7364	Intermediate Similarity	NPD6402	Approved
0.7364	Intermediate Similarity	NPD5739	Approved
0.7364	Intermediate Similarity	NPD7128	Approved
0.7364	Intermediate Similarity	NPD6675	Approved
0.734	Intermediate Similarity	NPD7339	Approved
0.734	Intermediate Similarity	NPD6942	Approved
0.7321	Intermediate Similarity	NPD6372	Approved
0.7321	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6373	Approved
0.7297	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6319	Approved
0.7273	Intermediate Similarity	NPD6695	Phase 3
0.7232	Intermediate Similarity	NPD6881	Approved
0.7232	Intermediate Similarity	NPD7320	Approved
0.7232	Intermediate Similarity	NPD6899	Approved
0.7222	Intermediate Similarity	NPD6648	Approved
0.7217	Intermediate Similarity	NPD4632	Approved
0.7212	Intermediate Similarity	NPD8035	Phase 2
0.7212	Intermediate Similarity	NPD8034	Phase 2
0.72	Intermediate Similarity	NPD4786	Approved
0.7193	Intermediate Similarity	NPD6649	Approved
0.7193	Intermediate Similarity	NPD8130	Phase 1
0.7193	Intermediate Similarity	NPD6650	Approved
0.7157	Intermediate Similarity	NPD7750	Discontinued
0.7157	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD5701	Approved
0.7143	Intermediate Similarity	NPD5697	Approved
0.713	Intermediate Similarity	NPD6882	Approved
0.713	Intermediate Similarity	NPD6053	Discontinued
0.7115	Intermediate Similarity	NPD7838	Discovery
0.7105	Intermediate Similarity	NPD6883	Approved
0.7105	Intermediate Similarity	NPD7290	Approved
0.7105	Intermediate Similarity	NPD7102	Approved
0.7083	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7748	Approved
0.7073	Intermediate Similarity	NPD8293	Discontinued
0.7054	Intermediate Similarity	NPD6008	Approved
0.7049	Intermediate Similarity	NPD7492	Approved
0.7043	Intermediate Similarity	NPD6869	Approved
0.7043	Intermediate Similarity	NPD6847	Approved
0.7043	Intermediate Similarity	NPD6617	Approved
0.7041	Intermediate Similarity	NPD7645	Phase 2
0.7041	Intermediate Similarity	NPD6929	Approved
0.7037	Intermediate Similarity	NPD6084	Phase 2
0.7037	Intermediate Similarity	NPD6083	Phase 2
0.7037	Intermediate Similarity	NPD7902	Approved
0.7034	Intermediate Similarity	NPD6009	Approved
0.7019	Intermediate Similarity	NPD5328	Approved
0.7018	Intermediate Similarity	NPD6012	Approved
0.7018	Intermediate Similarity	NPD6013	Approved
0.7018	Intermediate Similarity	NPD6014	Approved
0.7016	Intermediate Similarity	NPD7736	Approved
0.7	Intermediate Similarity	NPD3667	Approved
0.7	Intermediate Similarity	NPD4159	Approved
0.7	Intermediate Similarity	NPD6054	Approved
0.7	Intermediate Similarity	NPD6059	Approved
0.6992	Remote Similarity	NPD6616	Approved
0.697	Remote Similarity	NPD6930	Phase 2
0.697	Remote Similarity	NPD6931	Approved
0.6967	Remote Similarity	NPD7604	Phase 2
0.6961	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6698	Approved
0.6952	Remote Similarity	NPD46	Approved
0.6942	Remote Similarity	NPD5983	Phase 2
0.6935	Remote Similarity	NPD7078	Approved
0.693	Remote Similarity	NPD6011	Approved
0.6897	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD3618	Phase 1
0.6891	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7515	Phase 2
0.6887	Remote Similarity	NPD6079	Approved
0.6885	Remote Similarity	NPD6370	Approved
0.6881	Remote Similarity	NPD4755	Approved
0.6855	Remote Similarity	NPD6336	Discontinued
0.6837	Remote Similarity	NPD6925	Approved
0.6837	Remote Similarity	NPD5776	Phase 2
0.6829	Remote Similarity	NPD8328	Phase 3
0.6822	Remote Similarity	NPD4202	Approved
0.6803	Remote Similarity	NPD8513	Phase 3
0.6803	Remote Similarity	NPD6016	Approved
0.6803	Remote Similarity	NPD8515	Approved
0.6803	Remote Similarity	NPD8517	Approved
0.6803	Remote Similarity	NPD8516	Approved
0.6803	Remote Similarity	NPD6015	Approved
0.68	Remote Similarity	NPD7514	Phase 3
0.6786	Remote Similarity	NPD5211	Phase 2
0.6768	Remote Similarity	NPD7145	Approved
0.6762	Remote Similarity	NPD6672	Approved
0.6762	Remote Similarity	NPD5737	Approved
0.6759	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7900	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
0.6748	Remote Similarity	NPD5988	Approved
0.6735	Remote Similarity	NPD6933	Approved
0.6733	Remote Similarity	NPD6902	Approved
0.6731	Remote Similarity	NPD6409	Approved
0.6731	Remote Similarity	NPD7521	Approved
0.6731	Remote Similarity	NPD6684	Approved
0.6731	Remote Similarity	NPD5330	Approved
0.6731	Remote Similarity	NPD7334	Approved
0.6731	Remote Similarity	NPD7146	Approved
0.6729	Remote Similarity	NPD7087	Discontinued
0.6701	Remote Similarity	NPD6926	Approved
0.6701	Remote Similarity	NPD6924	Approved
0.6699	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD6932	Approved
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6639	Remote Similarity	NPD7101	Approved
0.6639	Remote Similarity	NPD7100	Approved
0.6637	Remote Similarity	NPD4633	Approved
0.6637	Remote Similarity	NPD5224	Approved
0.6637	Remote Similarity	NPD5226	Approved
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
0.6635	Remote Similarity	NPD6893	Approved
0.6635	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7332	Phase 2
0.661	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4768	Approved
0.6609	Remote Similarity	NPD4767	Approved
0.6604	Remote Similarity	NPD6903	Approved
0.6604	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6114	Approved
0.66	Remote Similarity	NPD6115	Approved
0.66	Remote Similarity	NPD6118	Approved
0.66	Remote Similarity	NPD6697	Approved
0.6589	Remote Similarity	NPD7260	Phase 2
0.6579	Remote Similarity	NPD5174	Approved
0.6579	Remote Similarity	NPD5175	Approved
0.6577	Remote Similarity	NPD5173	Approved
0.6574	Remote Similarity	NPD5693	Phase 1
0.6574	Remote Similarity	NPD6411	Approved
0.6574	Remote Similarity	NPD7983	Approved
0.656	Remote Similarity	NPD6067	Discontinued
0.6557	Remote Similarity	NPD6335	Approved
0.6552	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5223	Approved
0.6545	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4753	Phase 2
0.6538	Remote Similarity	NPD3666	Approved
0.6538	Remote Similarity	NPD3133	Approved
0.6538	Remote Similarity	NPD3665	Phase 1
0.6538	Remote Similarity	NPD3668	Phase 3
0.6535	Remote Similarity	NPD8074	Phase 3
0.6535	Remote Similarity	NPD6683	Phase 2
0.6532	Remote Similarity	NPD6909	Approved
0.6532	Remote Similarity	NPD6908	Approved
0.6532	Remote Similarity	NPD6921	Approved
0.6531	Remote Similarity	NPD4784	Approved
0.6531	Remote Similarity	NPD4785	Approved
0.6529	Remote Similarity	NPD6868	Approved
0.6525	Remote Similarity	NPD6371	Approved
0.6522	Remote Similarity	NPD7625	Phase 1

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