NPASS Compound

Structure

NPC475558 OpenBabel07101719522D 46 49 0 0 1 0 0 0 0 0999 V2000 -2.5472 -2.4190 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 -3.1653 -4.3212 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 7.9282 1.0000 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 9.5263 -0.5000 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 -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 -1.5388 0.5000 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 3.4641 1.0000 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 6.9282 -0.0000 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 -1.8781 -3.1622 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 -2.1871 -4.1132 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 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 2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5180 -4.8564 0.0000 C 0 0 0 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 6.9282 1.0000 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 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8270 -5.8074 0.0000 O 0 0 0 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 7.4282 1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 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 22 2 0 0 0 0 4 34 1 0 0 0 0 5 34 1 0 0 0 0 8 37 1 0 0 0 0 10 45 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 26 1 0 0 0 0 14 28 1 0 0 0 0 15 18 1 0 0 0 0 15 25 1 0 0 0 0 16 17 1 0 0 0 0 16 30 1 0 0 0 0 17 36 1 0 0 0 0 18 37 1 0 0 0 0 19 27 1 0 0 0 0 19 29 1 0 0 0 0 20 31 1 0 0 0 0 20 35 1 0 0 0 0 21 32 1 0 0 0 0 21 35 1 0 0 0 0 22 24 1 0 0 0 0 23 2 1 1 0 0 0 23 25 1 0 0 0 0 24 3 1 1 0 0 0 24 33 1 0 0 0 0 25 38 1 1 0 0 0 26 27 2 0 0 0 0 26 37 1 0 0 0 0 27 36 1 0 0 0 0 28 34 1 0 0 0 0 28 36 1 1 0 0 0 29 38 1 6 0 0 0 29 39 1 0 0 0 0 30 34 1 0 0 0 0 30 46 1 6 0 0 0 31 40 2 0 0 0 0 31 45 1 0 0 0 0 32 41 2 0 0 0 0 32 46 1 0 0 0 0 33 42 2 0 0 0 0 33 43 1 0 0 0 0 35 6 1 1 0 0 0 35 44 1 0 0 0 0 36 7 1 1 0 0 0 37 38 1 6 0 0 0 38 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	644.43
Volume:	688.718
LogP:	5.778
LogD:	4.628
LogS:	-5.008
# Rotatable Bonds:	12
TPSA:	130.36
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.171
Synthetic Accessibility Score:	5.455
Fsp3:	0.816
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:	-5.37
MDCK Permeability:	1.1196832019777503e-05
Pgp-inhibitor:	0.695
Pgp-substrate:	0.147
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	0.873

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.119
Plasma Protein Binding (PPB):	92.47149658203125%
Volume Distribution (VD):	0.497
Pgp-substrate:	3.3250973224639893%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.16
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.219
CYP2C9-substrate:	0.406
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.467
CYP3A4-substrate:	0.616

ADMET: Excretion

Clearance (CL):	6.473
Half-life (T1/2):	0.358

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.367
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.127
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.671
Carcinogencity:	0.096
Eye Corrosion:	0.125
Eye Irritation:	0.027
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC475558

Natural Product ID:	NPC475558
*Common Name:**	(25S,3's)-(+)-12Alpha-Hydroxy-3Alpha-(3'-Hydroxy-4'-Methoxycarbonyl-3'-Methylbutyryloxy)-24-Methyllanosta-8,24-(31)-Dien-26-Oic Acid
IUPAC Name:	(2S,6R)-6-[(3R,5R,10S,12S,13R,14S,17R)-12-hydroxy-3-[(3R)-3-hydroxy-5-methoxy-3-methyl-5-oxopentanoyl]oxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-3-methylideneheptanoic acid
Synonyms:
Standard InCHIKey:	JJYYLQGYXTZKMO-DZBUOOPSSA-N
Standard InCHI:	InChI=1S/C38H60O8/c1-22(24(3)33(42)43)11-12-23(2)25-15-18-37(8)26-13-14-28-34(4,5)30(46-32(41)21-35(6,44)20-31(40)45-10)16-17-36(28,7)27(26)19-29(39)38(25,37)9/h23-25,28-30,39,44H,1,11-21H2,2-10H3,(H,42,43)/t23-,24+,25-,28+,29+,30-,35-,36-,37+,38+/m1/s1
SMILES:	COC(=O)C[C@](CC(=O)O[C@@H]1CC[C@]2([C@H](C1(C)C)CCC1=C2C[C@H](O)[C@]2([C@@]1(C)CC[C@@H]2[C@@H](CCC(=C)[C@@H](C(=O)O)C)C)C)C)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508100
PubChem CID:	44559653
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
NPO8228	Piptoporus betulinus	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11099232]
NPO8228	Piptoporus betulinus	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932134]

☑ 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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	86.0	%	PMID[504076]

☑ 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 NPC475558 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	199
0.1-0.2	1309
0.2-0.3	4705
0.3-0.4	10519
0.4-0.5	10956
0.5-0.6	6087
0.6-0.7	6457
0.7-0.8	2321
0.8-0.85	115
0.85-0.9	22
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473788
0.9263	High Similarity	NPC120708
0.9184	High Similarity	NPC296879
0.9184	High Similarity	NPC471119
0.9091	High Similarity	NPC55954
0.9091	High Similarity	NPC218513
0.8911	High Similarity	NPC475494
0.8842	High Similarity	NPC26888
0.883	High Similarity	NPC474889
0.8774	High Similarity	NPC116024
0.8737	High Similarity	NPC175628
0.8737	High Similarity	NPC148414
0.8737	High Similarity	NPC111585
0.8723	High Similarity	NPC242864
0.87	High Similarity	NPC473514
0.8687	High Similarity	NPC119036
0.8627	High Similarity	NPC96268
0.8624	High Similarity	NPC472933
0.8611	High Similarity	NPC472934
0.8571	High Similarity	NPC317586
0.8571	High Similarity	NPC69548
0.8571	High Similarity	NPC279974
0.8571	High Similarity	NPC184848
0.8571	High Similarity	NPC90630
0.8571	High Similarity	NPC473648
0.8571	High Similarity	NPC470016
0.8571	High Similarity	NPC48330
0.8571	High Similarity	NPC475243
0.8542	High Similarity	NPC469400
0.8542	High Similarity	NPC471896
0.8529	High Similarity	NPC159442
0.8511	High Similarity	NPC55309
0.8511	High Similarity	NPC28252
0.8505	High Similarity	NPC472926
0.8485	Intermediate Similarity	NPC327788
0.8485	Intermediate Similarity	NPC173272
0.8485	Intermediate Similarity	NPC42042
0.8476	Intermediate Similarity	NPC218853
0.8469	Intermediate Similarity	NPC166906
0.844	Intermediate Similarity	NPC472927
0.8438	Intermediate Similarity	NPC475921
0.8438	Intermediate Similarity	NPC474704
0.8421	Intermediate Similarity	NPC159046
0.8421	Intermediate Similarity	NPC233836
0.8421	Intermediate Similarity	NPC187376
0.8416	Intermediate Similarity	NPC94906
0.8411	Intermediate Similarity	NPC280782
0.84	Intermediate Similarity	NPC253586
0.8381	Intermediate Similarity	NPC472219
0.8381	Intermediate Similarity	NPC472218
0.8381	Intermediate Similarity	NPC195708
0.8381	Intermediate Similarity	NPC472217
0.8367	Intermediate Similarity	NPC471902
0.8367	Intermediate Similarity	NPC287118
0.8367	Intermediate Similarity	NPC473690
0.8365	Intermediate Similarity	NPC231530
0.8365	Intermediate Similarity	NPC196528
0.8365	Intermediate Similarity	NPC278628
0.8365	Intermediate Similarity	NPC472935
0.8351	Intermediate Similarity	NPC20388
0.835	Intermediate Similarity	NPC222153
0.8333	Intermediate Similarity	NPC75941
0.8333	Intermediate Similarity	NPC52634
0.8317	Intermediate Similarity	NPC472028
0.8317	Intermediate Similarity	NPC477813
0.8317	Intermediate Similarity	NPC477854
0.8302	Intermediate Similarity	NPC477069
0.8302	Intermediate Similarity	NPC477070
0.8302	Intermediate Similarity	NPC475364
0.8302	Intermediate Similarity	NPC265655
0.83	Intermediate Similarity	NPC305483
0.83	Intermediate Similarity	NPC328162
0.83	Intermediate Similarity	NPC96859
0.8286	Intermediate Similarity	NPC59530
0.8283	Intermediate Similarity	NPC474922
0.8269	Intermediate Similarity	NPC471293
0.8269	Intermediate Similarity	NPC475036
0.8269	Intermediate Similarity	NPC216245
0.8269	Intermediate Similarity	NPC2436
0.8269	Intermediate Similarity	NPC135854
0.8269	Intermediate Similarity	NPC470251
0.8265	Intermediate Similarity	NPC475416
0.8265	Intermediate Similarity	NPC297265
0.8265	Intermediate Similarity	NPC23434
0.8265	Intermediate Similarity	NPC471901
0.8257	Intermediate Similarity	NPC470953
0.8252	Intermediate Similarity	NPC124544
0.8252	Intermediate Similarity	NPC22388
0.8247	Intermediate Similarity	NPC77168
0.8247	Intermediate Similarity	NPC84271
0.8247	Intermediate Similarity	NPC102414
0.8247	Intermediate Similarity	NPC474570
0.8241	Intermediate Similarity	NPC233003
0.8235	Intermediate Similarity	NPC167974
0.8235	Intermediate Similarity	NPC287676
0.8235	Intermediate Similarity	NPC108371
0.8235	Intermediate Similarity	NPC241221
0.8235	Intermediate Similarity	NPC316964
0.8229	Intermediate Similarity	NPC142361
0.8229	Intermediate Similarity	NPC474684
0.8224	Intermediate Similarity	NPC197428
0.8224	Intermediate Similarity	NPC129689
0.8224	Intermediate Similarity	NPC250956
0.8224	Intermediate Similarity	NPC129340
0.8218	Intermediate Similarity	NPC320306
0.8218	Intermediate Similarity	NPC43747
0.8208	Intermediate Similarity	NPC163216
0.8208	Intermediate Similarity	NPC258323
0.8208	Intermediate Similarity	NPC94529
0.82	Intermediate Similarity	NPC23241
0.82	Intermediate Similarity	NPC195715
0.82	Intermediate Similarity	NPC469599
0.819	Intermediate Similarity	NPC472655
0.8182	Intermediate Similarity	NPC470224
0.8182	Intermediate Similarity	NPC206810
0.8182	Intermediate Similarity	NPC476963
0.8173	Intermediate Similarity	NPC33973
0.8173	Intermediate Similarity	NPC36688
0.8173	Intermediate Similarity	NPC70967
0.8165	Intermediate Similarity	NPC251309
0.8165	Intermediate Similarity	NPC472929
0.8155	Intermediate Similarity	NPC163963
0.8155	Intermediate Similarity	NPC52899
0.8155	Intermediate Similarity	NPC289148
0.8155	Intermediate Similarity	NPC236585
0.8148	Intermediate Similarity	NPC477073
0.8148	Intermediate Similarity	NPC115303
0.8148	Intermediate Similarity	NPC472928
0.8148	Intermediate Similarity	NPC292196
0.8144	Intermediate Similarity	NPC471724
0.8137	Intermediate Similarity	NPC474793
0.8137	Intermediate Similarity	NPC16911
0.8137	Intermediate Similarity	NPC78427
0.8131	Intermediate Similarity	NPC77947
0.8131	Intermediate Similarity	NPC5475
0.8131	Intermediate Similarity	NPC472216
0.8131	Intermediate Similarity	NPC284828
0.8131	Intermediate Similarity	NPC173905
0.8131	Intermediate Similarity	NPC304495
0.8131	Intermediate Similarity	NPC286174
0.8125	Intermediate Similarity	NPC325594
0.8125	Intermediate Similarity	NPC474970
0.8125	Intermediate Similarity	NPC155011
0.8125	Intermediate Similarity	NPC73038
0.8119	Intermediate Similarity	NPC329910
0.8119	Intermediate Similarity	NPC477853
0.8119	Intermediate Similarity	NPC328371
0.8119	Intermediate Similarity	NPC7124
0.8113	Intermediate Similarity	NPC220974
0.8113	Intermediate Similarity	NPC472925
0.8108	Intermediate Similarity	NPC476959
0.81	Intermediate Similarity	NPC159410
0.81	Intermediate Similarity	NPC184006
0.81	Intermediate Similarity	NPC47853
0.81	Intermediate Similarity	NPC469406
0.81	Intermediate Similarity	NPC240617
0.81	Intermediate Similarity	NPC23621
0.81	Intermediate Similarity	NPC78580
0.8095	Intermediate Similarity	NPC98603
0.8091	Intermediate Similarity	NPC220293
0.8081	Intermediate Similarity	NPC189520
0.8077	Intermediate Similarity	NPC119601
0.8077	Intermediate Similarity	NPC304832
0.8077	Intermediate Similarity	NPC475320
0.8077	Intermediate Similarity	NPC281702
0.8077	Intermediate Similarity	NPC148628
0.8077	Intermediate Similarity	NPC275990
0.8077	Intermediate Similarity	NPC88203
0.8077	Intermediate Similarity	NPC53222
0.8077	Intermediate Similarity	NPC286519
0.8077	Intermediate Similarity	NPC477054
0.8077	Intermediate Similarity	NPC246736
0.8077	Intermediate Similarity	NPC473928
0.8077	Intermediate Similarity	NPC193934
0.8077	Intermediate Similarity	NPC76866
0.8077	Intermediate Similarity	NPC214946
0.8077	Intermediate Similarity	NPC308726
0.8077	Intermediate Similarity	NPC271980
0.8061	Intermediate Similarity	NPC57954
0.8061	Intermediate Similarity	NPC213832
0.8058	Intermediate Similarity	NPC157787
0.8058	Intermediate Similarity	NPC83709
0.8058	Intermediate Similarity	NPC327431
0.8058	Intermediate Similarity	NPC37047
0.8058	Intermediate Similarity	NPC307954
0.8058	Intermediate Similarity	NPC477521
0.8058	Intermediate Similarity	NPC88198
0.8058	Intermediate Similarity	NPC41971
0.8058	Intermediate Similarity	NPC180733
0.8056	Intermediate Similarity	NPC101450
0.8041	Intermediate Similarity	NPC96496
0.8039	Intermediate Similarity	NPC476879
0.8039	Intermediate Similarity	NPC476878
0.8039	Intermediate Similarity	NPC108078
0.802	Intermediate Similarity	NPC469329
0.802	Intermediate Similarity	NPC30677
0.802	Intermediate Similarity	NPC210214
0.802	Intermediate Similarity	NPC173875
0.802	Intermediate Similarity	NPC162001
0.802	Intermediate Similarity	NPC255809

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 NPC475558 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1698
0.2-0.3	3912
0.3-0.4	2217
0.4-0.5	632
0.5-0.6	224
0.6-0.7	217
0.7-0.8	87
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
0.8019	Intermediate Similarity	NPD7128	Approved
0.8019	Intermediate Similarity	NPD5739	Approved
0.8019	Intermediate Similarity	NPD6675	Approved
0.8019	Intermediate Similarity	NPD6402	Approved
0.8	Intermediate Similarity	NPD6399	Phase 3
0.7963	Intermediate Similarity	NPD6373	Approved
0.7963	Intermediate Similarity	NPD6372	Approved
0.7909	Intermediate Similarity	NPD8297	Approved
0.79	Intermediate Similarity	NPD6411	Approved
0.787	Intermediate Similarity	NPD6881	Approved
0.787	Intermediate Similarity	NPD6899	Approved
0.787	Intermediate Similarity	NPD7320	Approved
0.7818	Intermediate Similarity	NPD6650	Approved
0.7818	Intermediate Similarity	NPD8130	Phase 1
0.7818	Intermediate Similarity	NPD6649	Approved
0.7778	Intermediate Similarity	NPD5697	Approved
0.7778	Intermediate Similarity	NPD5701	Approved
0.7748	Intermediate Similarity	NPD6882	Approved
0.7739	Intermediate Similarity	NPD6319	Approved
0.7732	Intermediate Similarity	NPD4786	Approved
0.7727	Intermediate Similarity	NPD7290	Approved
0.7727	Intermediate Similarity	NPD6883	Approved
0.7727	Intermediate Similarity	NPD7102	Approved
0.7723	Intermediate Similarity	NPD8035	Phase 2
0.7723	Intermediate Similarity	NPD8034	Phase 2
0.77	Intermediate Similarity	NPD6101	Approved
0.77	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD5328	Approved
0.7692	Intermediate Similarity	NPD6083	Phase 2
0.7692	Intermediate Similarity	NPD6084	Phase 2
0.767	Intermediate Similarity	NPD5695	Phase 3
0.7658	Intermediate Similarity	NPD6869	Approved
0.7658	Intermediate Similarity	NPD6847	Approved
0.7658	Intermediate Similarity	NPD6617	Approved
0.7653	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6012	Approved
0.7636	Intermediate Similarity	NPD6014	Approved
0.7636	Intermediate Similarity	NPD6013	Approved
0.7632	Intermediate Similarity	NPD7115	Discovery
0.7619	Intermediate Similarity	NPD7638	Approved
0.7573	Intermediate Similarity	NPD7748	Approved
0.7549	Intermediate Similarity	NPD6079	Approved
0.7547	Intermediate Similarity	NPD7640	Approved
0.7547	Intermediate Similarity	NPD7639	Approved
0.7545	Intermediate Similarity	NPD6011	Approved
0.7526	Intermediate Similarity	NPD3667	Approved
0.7524	Intermediate Similarity	NPD4755	Approved
0.7523	Intermediate Similarity	NPD6008	Approved
0.75	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8293	Discontinued
0.7479	Intermediate Similarity	NPD7492	Approved
0.7476	Intermediate Similarity	NPD5779	Approved
0.7476	Intermediate Similarity	NPD5778	Approved
0.7453	Intermediate Similarity	NPD5696	Approved
0.7438	Intermediate Similarity	NPD7736	Approved
0.7436	Intermediate Similarity	NPD6054	Approved
0.7436	Intermediate Similarity	NPD6059	Approved
0.7417	Intermediate Similarity	NPD6616	Approved
0.74	Intermediate Similarity	NPD3618	Phase 1
0.7383	Intermediate Similarity	NPD5286	Approved
0.7383	Intermediate Similarity	NPD5285	Approved
0.7383	Intermediate Similarity	NPD4700	Approved
0.7383	Intermediate Similarity	NPD4696	Approved
0.7379	Intermediate Similarity	NPD7515	Phase 2
0.7368	Intermediate Similarity	NPD4632	Approved
0.7358	Intermediate Similarity	NPD7902	Approved
0.7355	Intermediate Similarity	NPD7078	Approved
0.7328	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6370	Approved
0.7308	Intermediate Similarity	NPD4202	Approved
0.7264	Intermediate Similarity	NPD5222	Approved
0.7264	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD4697	Phase 3
0.7264	Intermediate Similarity	NPD5221	Approved
0.7257	Intermediate Similarity	NPD4634	Approved
0.7255	Intermediate Similarity	NPD6672	Approved
0.7255	Intermediate Similarity	NPD5737	Approved
0.7248	Intermediate Similarity	NPD5226	Approved
0.7248	Intermediate Similarity	NPD5224	Approved
0.7248	Intermediate Similarity	NPD5211	Phase 2
0.7248	Intermediate Similarity	NPD5225	Approved
0.7248	Intermediate Similarity	NPD4633	Approved
0.7241	Intermediate Similarity	NPD6274	Approved
0.7236	Intermediate Similarity	NPD7319	Approved
0.7228	Intermediate Similarity	NPD6684	Approved
0.7228	Intermediate Similarity	NPD5330	Approved
0.7228	Intermediate Similarity	NPD7334	Approved
0.7228	Intermediate Similarity	NPD7521	Approved
0.7228	Intermediate Similarity	NPD7146	Approved
0.7228	Intermediate Similarity	NPD6409	Approved
0.7227	Intermediate Similarity	NPD6016	Approved
0.7227	Intermediate Similarity	NPD6015	Approved
0.7212	Intermediate Similarity	NPD7637	Suspended
0.7207	Intermediate Similarity	NPD4768	Approved
0.7207	Intermediate Similarity	NPD4767	Approved
0.7203	Intermediate Similarity	NPD7101	Approved
0.7203	Intermediate Similarity	NPD7100	Approved
0.7196	Intermediate Similarity	NPD5173	Approved
0.7184	Intermediate Similarity	NPD4753	Phase 2
0.7182	Intermediate Similarity	NPD5174	Approved
0.7182	Intermediate Similarity	NPD5175	Approved
0.7179	Intermediate Similarity	NPD6009	Approved
0.717	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5988	Approved
0.7156	Intermediate Similarity	NPD5223	Approved
0.7143	Intermediate Similarity	NPD7525	Registered
0.7131	Intermediate Similarity	NPD7507	Approved
0.713	Intermediate Similarity	NPD6053	Discontinued
0.7119	Intermediate Similarity	NPD6335	Approved
0.7117	Intermediate Similarity	NPD5141	Approved
0.7113	Intermediate Similarity	NPD6115	Approved
0.7113	Intermediate Similarity	NPD6114	Approved
0.7113	Intermediate Similarity	NPD6697	Approved
0.7113	Intermediate Similarity	NPD6118	Approved
0.7107	Intermediate Similarity	NPD8328	Phase 3
0.7107	Intermediate Similarity	NPD7604	Phase 2
0.7094	Intermediate Similarity	NPD6868	Approved
0.7091	Intermediate Similarity	NPD7632	Discontinued
0.7087	Intermediate Similarity	NPD6903	Approved
0.7087	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5983	Phase 2
0.7083	Intermediate Similarity	NPD6909	Approved
0.7083	Intermediate Similarity	NPD6117	Approved
0.7083	Intermediate Similarity	NPD6908	Approved
0.708	Intermediate Similarity	NPD4730	Approved
0.708	Intermediate Similarity	NPD4729	Approved
0.7075	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7900	Approved
0.7069	Intermediate Similarity	NPD8133	Approved
0.7059	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6098	Approved
0.7059	Intermediate Similarity	NPD5279	Phase 3
0.7048	Intermediate Similarity	NPD5284	Approved
0.7048	Intermediate Similarity	NPD5281	Approved
0.7048	Intermediate Similarity	NPD6050	Approved
0.7034	Intermediate Similarity	NPD6317	Approved
0.703	Intermediate Similarity	NPD3666	Approved
0.703	Intermediate Similarity	NPD3665	Phase 1
0.703	Intermediate Similarity	NPD3668	Phase 3
0.703	Intermediate Similarity	NPD3133	Approved
0.7027	Intermediate Similarity	NPD4754	Approved
0.7019	Intermediate Similarity	NPD6673	Approved
0.7019	Intermediate Similarity	NPD6080	Approved
0.7019	Intermediate Similarity	NPD6904	Approved
0.7018	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6116	Phase 1
0.7009	Intermediate Similarity	NPD4629	Approved
0.7009	Intermediate Similarity	NPD5210	Approved
0.6992	Remote Similarity	NPD6336	Discontinued
0.6991	Remote Similarity	NPD6412	Phase 2
0.6979	Remote Similarity	NPD7339	Approved
0.6979	Remote Similarity	NPD6942	Approved
0.6975	Remote Similarity	NPD6314	Approved
0.6975	Remote Similarity	NPD6313	Approved
0.6972	Remote Similarity	NPD4225	Approved
0.6957	Remote Similarity	NPD5251	Approved
0.6957	Remote Similarity	NPD5250	Approved
0.6957	Remote Similarity	NPD5249	Phase 3
0.6957	Remote Similarity	NPD5248	Approved
0.6957	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5247	Approved
0.6952	Remote Similarity	NPD5692	Phase 3
0.693	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5128	Approved
0.69	Remote Similarity	NPD5369	Approved
0.6887	Remote Similarity	NPD5694	Approved
0.688	Remote Similarity	NPD6033	Approved
0.6875	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4221	Approved
0.6832	Remote Similarity	NPD4223	Phase 3
0.6827	Remote Similarity	NPD3573	Approved
0.6803	Remote Similarity	NPD8513	Phase 3
0.6803	Remote Similarity	NPD8515	Approved
0.6803	Remote Similarity	NPD8517	Approved
0.6803	Remote Similarity	NPD8516	Approved
0.6803	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD8033	Approved
0.68	Remote Similarity	NPD4748	Discontinued
0.6796	Remote Similarity	NPD5329	Approved
0.6792	Remote Similarity	NPD5207	Approved
0.6783	Remote Similarity	NPD6686	Approved
0.6765	Remote Similarity	NPD6695	Phase 3
0.6765	Remote Similarity	NPD4788	Approved
0.6762	Remote Similarity	NPD5208	Approved
0.6759	Remote Similarity	NPD6001	Approved
0.6752	Remote Similarity	NPD5217	Approved
0.6752	Remote Similarity	NPD5216	Approved
0.6752	Remote Similarity	NPD5215	Approved
0.6735	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4692	Approved
0.6733	Remote Similarity	NPD4139	Approved
0.6731	Remote Similarity	NPD4694	Approved
0.6731	Remote Similarity	NPD5690	Phase 2
0.6731	Remote Similarity	NPD5280	Approved
0.6729	Remote Similarity	NPD7983	Approved
0.6729	Remote Similarity	NPD5693	Phase 1
0.6721	Remote Similarity	NPD8377	Approved
0.6721	Remote Similarity	NPD8294	Approved
0.67	Remote Similarity	NPD7645	Phase 2

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