NPASS Compound

Structure

NPC473648 OpenBabel07101719142D 41 44 0 0 1 0 0 0 0 0999 V2000 -2.2382 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 -3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 -5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 2.8660 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 0.8660 1.5000 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 -1.5388 -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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 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 -0.5909 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8781 -4.1622 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1871 -5.1132 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 2 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 -0.9000 -3.9543 0.0000 C 0 0 0 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 4.3301 1.5000 0.0000 C 0 0 2 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 -1.5180 -5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2308 -4.6974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8270 -6.8074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5398 -5.6485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 21 1 0 0 0 0 4 31 1 0 0 0 0 5 31 1 0 0 0 0 7 33 1 0 0 0 0 9 10 1 0 0 0 0 9 24 1 0 0 0 0 10 26 1 0 0 0 0 11 15 1 0 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 12 23 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 34 1 0 0 0 0 16 33 1 0 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 28 1 0 0 0 0 18 29 1 0 0 0 0 19 1 1 1 0 0 0 19 22 1 0 0 0 0 20 2 1 1 0 0 0 20 21 1 0 0 0 0 20 25 1 0 0 0 0 21 30 1 0 0 0 0 22 33 1 1 0 0 0 23 24 2 0 0 0 0 23 32 1 0 0 0 0 24 34 1 0 0 0 0 25 35 2 0 0 0 0 26 31 1 0 0 0 0 26 32 1 1 0 0 0 27 31 1 0 0 0 0 27 41 1 6 0 0 0 28 36 2 0 0 0 0 28 37 1 0 0 0 0 29 38 2 0 0 0 0 29 41 1 0 0 0 0 30 39 2 0 0 0 0 30 40 1 0 0 0 0 32 6 1 1 0 0 0 33 34 1 1 0 0 0 34 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	572.37
Volume:	610.743
LogP:	4.922
LogD:	3.944
LogS:	-4.439
# Rotatable Bonds:	10
TPSA:	117.97
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.172
Synthetic Accessibility Score:	5.024
Fsp3:	0.824
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:	-5.551
MDCK Permeability:	9.953227163350675e-06
Pgp-inhibitor:	0.052
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.921

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	92.77423858642578%
Volume Distribution (VD):	0.602
Pgp-substrate:	2.0968058109283447%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.301
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.92
CYP2C9-inhibitor:	0.142
CYP2C9-substrate:	0.987
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.058
CYP3A4-substrate:	0.152

ADMET: Excretion

Clearance (CL):	2.309
Half-life (T1/2):	0.697

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.484
Drug-inuced Liver Injury (DILI):	0.154
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.345
Maximum Recommended Daily Dose:	0.327
Skin Sensitization:	0.132
Carcinogencity:	0.057
Eye Corrosion:	0.861
Eye Irritation:	0.369
Respiratory Toxicity:	0.698

Download Data

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

Natural Product: NPC473648

Natural Product ID:	NPC473648
*Common Name:**	Carboxyacetylquercinic Acid
IUPAC Name:	(3R,6R)-6-[(3R,5R,10S,13R,14R,17R)-3-(2-carboxyacetyl)oxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2,3-dimethyl-4-oxoheptanoic acid
Synonyms:	Carboxyacetylquercinic Acid
Standard InCHIKey:	WWJFQSXVIHXIBB-XUPAHRBUSA-N
Standard InCHI:	InChI=1S/C34H52O7/c1-19(17-25(35)20(2)21(3)30(39)40)22-11-15-34(8)24-9-10-26-31(4,5)27(41-29(38)18-28(36)37)13-14-32(26,6)23(24)12-16-33(22,34)7/h19-22,26-27H,9-18H2,1-8H3,(H,36,37)(H,39,40)/t19-,20-,21?,22-,26+,27-,32-,33-,34+/m1/s1
SMILES:	CC(CC(=O)C(C)C(C)C(=O)O)C1CCC2(C1(CCC3=C2CCC4C3(CCC(C4(C)C)OC(=O)CC(=O)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448136
PubChem CID:	12019179
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
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)91122-1]
NPO32674	daedalea dickisii	Species	Coriolaceae	Eukaryota	fruit	n.a.	n.a.	PMID[15974617]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	Sri Lankan	n.a.	PMID[16933889]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27996259]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	45200.0	nM	PMID[466565]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	155200.0	nM	PMID[466565]
NPT168	Cell Line	P388	Mus musculus	Activity	>	125.0	ug ml-1	PMID[466566]

☑ 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 NPC473648 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	200
0.1-0.2	1495
0.2-0.3	5784
0.3-0.4	13612
0.4-0.5	8409
0.5-0.6	6159
0.6-0.7	5605
0.7-0.8	1299
0.8-0.85	115
0.85-0.9	16
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9462	High Similarity	NPC473514
0.9239	High Similarity	NPC120708
0.9	High Similarity	NPC474889
0.8901	High Similarity	NPC175628
0.8901	High Similarity	NPC111585
0.8901	High Similarity	NPC148414
0.8817	High Similarity	NPC159410
0.8804	High Similarity	NPC26888
0.8804	High Similarity	NPC297265
0.8723	High Similarity	NPC69548
0.8723	High Similarity	NPC184848
0.8696	High Similarity	NPC471896
0.8687	High Similarity	NPC475494
0.8632	High Similarity	NPC327788
0.86	High Similarity	NPC220974
0.8587	High Similarity	NPC474570
0.8571	High Similarity	NPC281702
0.8571	High Similarity	NPC473788
0.8571	High Similarity	NPC475558
0.8526	High Similarity	NPC255809
0.8511	High Similarity	NPC470254
0.8511	High Similarity	NPC170220
0.8511	High Similarity	NPC107674
0.8511	High Similarity	NPC141497
0.8495	Intermediate Similarity	NPC20388
0.8478	Intermediate Similarity	NPC242864
0.8462	Intermediate Similarity	NPC55309
0.8462	Intermediate Similarity	NPC28252
0.8454	Intermediate Similarity	NPC477813
0.8438	Intermediate Similarity	NPC7124
0.8438	Intermediate Similarity	NPC95565
0.8421	Intermediate Similarity	NPC471720
0.8404	Intermediate Similarity	NPC471901
0.8404	Intermediate Similarity	NPC86266
0.8404	Intermediate Similarity	NPC23434
0.8404	Intermediate Similarity	NPC110657
0.8404	Intermediate Similarity	NPC150383
0.8404	Intermediate Similarity	NPC107690
0.8404	Intermediate Similarity	NPC212301
0.84	Intermediate Similarity	NPC216245
0.84	Intermediate Similarity	NPC470251
0.84	Intermediate Similarity	NPC2436
0.84	Intermediate Similarity	NPC135854
0.8387	Intermediate Similarity	NPC475921
0.8387	Intermediate Similarity	NPC474704
0.8384	Intermediate Similarity	NPC53222
0.837	Intermediate Similarity	NPC233836
0.837	Intermediate Similarity	NPC187376
0.837	Intermediate Similarity	NPC159046
0.8367	Intermediate Similarity	NPC299971
0.8367	Intermediate Similarity	NPC144660
0.8367	Intermediate Similarity	NPC88198
0.8367	Intermediate Similarity	NPC307954
0.8333	Intermediate Similarity	NPC317586
0.8333	Intermediate Similarity	NPC470016
0.8316	Intermediate Similarity	NPC471902
0.8316	Intermediate Similarity	NPC473690
0.8316	Intermediate Similarity	NPC470224
0.8316	Intermediate Similarity	NPC287118
0.83	Intermediate Similarity	NPC33973
0.83	Intermediate Similarity	NPC70967
0.8298	Intermediate Similarity	NPC469400
0.8283	Intermediate Similarity	NPC124211
0.828	Intermediate Similarity	NPC80335
0.828	Intermediate Similarity	NPC471724
0.8265	Intermediate Similarity	NPC16021
0.8229	Intermediate Similarity	NPC184006
0.8229	Intermediate Similarity	NPC78580
0.8229	Intermediate Similarity	NPC184870
0.8229	Intermediate Similarity	NPC23621
0.8229	Intermediate Similarity	NPC166906
0.8229	Intermediate Similarity	NPC49670
0.8218	Intermediate Similarity	NPC96268
0.8211	Intermediate Similarity	NPC160506
0.8211	Intermediate Similarity	NPC475416
0.82	Intermediate Similarity	NPC296879
0.82	Intermediate Similarity	NPC56498
0.82	Intermediate Similarity	NPC471119
0.8191	Intermediate Similarity	NPC84271
0.8191	Intermediate Similarity	NPC102414
0.8191	Intermediate Similarity	NPC54689
0.8191	Intermediate Similarity	NPC77168
0.8182	Intermediate Similarity	NPC157787
0.8172	Intermediate Similarity	NPC167877
0.8172	Intermediate Similarity	NPC138756
0.8172	Intermediate Similarity	NPC474684
0.8172	Intermediate Similarity	NPC142361
0.8172	Intermediate Similarity	NPC96496
0.8163	Intermediate Similarity	NPC121339
0.8163	Intermediate Similarity	NPC106557
0.8163	Intermediate Similarity	NPC122294
0.8163	Intermediate Similarity	NPC26413
0.8144	Intermediate Similarity	NPC195715
0.8144	Intermediate Similarity	NPC469599
0.8144	Intermediate Similarity	NPC210214
0.8144	Intermediate Similarity	NPC263347
0.8144	Intermediate Similarity	NPC279974
0.8144	Intermediate Similarity	NPC45324
0.8144	Intermediate Similarity	NPC222845
0.8144	Intermediate Similarity	NPC162001
0.8144	Intermediate Similarity	NPC37787
0.8144	Intermediate Similarity	NPC473415
0.8144	Intermediate Similarity	NPC180557
0.8144	Intermediate Similarity	NPC23241
0.8144	Intermediate Similarity	NPC469329
0.8144	Intermediate Similarity	NPC30677
0.8125	Intermediate Similarity	NPC25750
0.8125	Intermediate Similarity	NPC470375
0.8125	Intermediate Similarity	NPC470376
0.8119	Intermediate Similarity	NPC218513
0.8119	Intermediate Similarity	NPC55954
0.8119	Intermediate Similarity	NPC159442
0.8113	Intermediate Similarity	NPC52634
0.8105	Intermediate Similarity	NPC473269
0.8105	Intermediate Similarity	NPC44240
0.8105	Intermediate Similarity	NPC161638
0.8085	Intermediate Similarity	NPC183546
0.8085	Intermediate Similarity	NPC4309
0.8081	Intermediate Similarity	NPC112753
0.8081	Intermediate Similarity	NPC119036
0.8081	Intermediate Similarity	NPC275439
0.8081	Intermediate Similarity	NPC164349
0.8065	Intermediate Similarity	NPC325594
0.8065	Intermediate Similarity	NPC72133
0.8065	Intermediate Similarity	NPC472491
0.8065	Intermediate Similarity	NPC472494
0.8061	Intermediate Similarity	NPC3772
0.8061	Intermediate Similarity	NPC96859
0.8061	Intermediate Similarity	NPC125622
0.8061	Intermediate Similarity	NPC243525
0.8061	Intermediate Similarity	NPC328162
0.8061	Intermediate Similarity	NPC471153
0.8061	Intermediate Similarity	NPC40765
0.8061	Intermediate Similarity	NPC42042
0.8061	Intermediate Similarity	NPC305483
0.8061	Intermediate Similarity	NPC471777
0.8058	Intermediate Similarity	NPC473037
0.8043	Intermediate Similarity	NPC109512
0.8043	Intermediate Similarity	NPC319909
0.8043	Intermediate Similarity	NPC209882
0.8041	Intermediate Similarity	NPC473280
0.8041	Intermediate Similarity	NPC473431
0.8041	Intermediate Similarity	NPC471078
0.8041	Intermediate Similarity	NPC473435
0.8041	Intermediate Similarity	NPC469406
0.8039	Intermediate Similarity	NPC28656
0.8022	Intermediate Similarity	NPC133391
0.8022	Intermediate Similarity	NPC240302
0.8021	Intermediate Similarity	NPC154101
0.8021	Intermediate Similarity	NPC235704
0.8021	Intermediate Similarity	NPC189520
0.802	Intermediate Similarity	NPC234892
0.802	Intermediate Similarity	NPC22388
0.8	Intermediate Similarity	NPC205899
0.8	Intermediate Similarity	NPC35751
0.8	Intermediate Similarity	NPC57954
0.8	Intermediate Similarity	NPC30522
0.8	Intermediate Similarity	NPC316964
0.8	Intermediate Similarity	NPC213832
0.8	Intermediate Similarity	NPC477521
0.798	Intermediate Similarity	NPC320306
0.798	Intermediate Similarity	NPC89225
0.798	Intermediate Similarity	NPC23680
0.798	Intermediate Similarity	NPC216904
0.7979	Intermediate Similarity	NPC472493
0.7959	Intermediate Similarity	NPC37646
0.7959	Intermediate Similarity	NPC48330
0.7959	Intermediate Similarity	NPC241156
0.7959	Intermediate Similarity	NPC88310
0.7959	Intermediate Similarity	NPC205173
0.7959	Intermediate Similarity	NPC297199
0.7957	Intermediate Similarity	NPC478127
0.7957	Intermediate Similarity	NPC473038
0.7944	Intermediate Similarity	NPC472929
0.7941	Intermediate Similarity	NPC72151
0.7941	Intermediate Similarity	NPC55872
0.7941	Intermediate Similarity	NPC36321
0.7941	Intermediate Similarity	NPC470310
0.7938	Intermediate Similarity	NPC294263
0.7938	Intermediate Similarity	NPC152897
0.7938	Intermediate Similarity	NPC66429
0.7938	Intermediate Similarity	NPC243866
0.7938	Intermediate Similarity	NPC86368
0.7935	Intermediate Similarity	NPC476100
0.7935	Intermediate Similarity	NPC471037
0.7935	Intermediate Similarity	NPC472492
0.7935	Intermediate Similarity	NPC271784
0.7935	Intermediate Similarity	NPC477373
0.7935	Intermediate Similarity	NPC469561
0.7925	Intermediate Similarity	NPC115303
0.7921	Intermediate Similarity	NPC477052
0.7921	Intermediate Similarity	NPC477053
0.7921	Intermediate Similarity	NPC477051
0.7917	Intermediate Similarity	NPC136801
0.7917	Intermediate Similarity	NPC289213
0.7917	Intermediate Similarity	NPC113989
0.7917	Intermediate Similarity	NPC477149
0.7917	Intermediate Similarity	NPC120840
0.7917	Intermediate Similarity	NPC477147
0.7912	Intermediate Similarity	NPC201912

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 NPC473648 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1959
0.2-0.3	4020
0.3-0.4	2013
0.4-0.5	539
0.5-0.6	183
0.6-0.7	186
0.7-0.8	73
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8511	High Similarity	NPD6399	Phase 3
0.8211	Intermediate Similarity	NPD8034	Phase 2
0.8211	Intermediate Similarity	NPD8035	Phase 2
0.798	Intermediate Similarity	NPD7902	Approved
0.7905	Intermediate Similarity	NPD6373	Approved
0.7905	Intermediate Similarity	NPD6372	Approved
0.7857	Intermediate Similarity	NPD7748	Approved
0.7788	Intermediate Similarity	NPD7128	Approved
0.7788	Intermediate Similarity	NPD5739	Approved
0.7788	Intermediate Similarity	NPD6675	Approved
0.7788	Intermediate Similarity	NPD6402	Approved
0.7778	Intermediate Similarity	NPD5695	Phase 3
0.7757	Intermediate Similarity	NPD6649	Approved
0.7757	Intermediate Similarity	NPD6650	Approved
0.7684	Intermediate Similarity	NPD3618	Phase 1
0.7677	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD7900	Approved
0.766	Intermediate Similarity	NPD4786	Approved
0.7642	Intermediate Similarity	NPD7320	Approved
0.7642	Intermediate Similarity	NPD6899	Approved
0.7642	Intermediate Similarity	NPD6881	Approved
0.7629	Intermediate Similarity	NPD5328	Approved
0.7624	Intermediate Similarity	NPD6084	Phase 2
0.7624	Intermediate Similarity	NPD6083	Phase 2
0.7593	Intermediate Similarity	NPD8130	Phase 1
0.7579	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7115	Discovery
0.7549	Intermediate Similarity	NPD5696	Approved
0.7547	Intermediate Similarity	NPD5701	Approved
0.7547	Intermediate Similarity	NPD5697	Approved
0.7526	Intermediate Similarity	NPD6672	Approved
0.7526	Intermediate Similarity	NPD5737	Approved
0.7525	Intermediate Similarity	NPD4697	Phase 3
0.7523	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD6684	Approved
0.75	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD7334	Approved
0.75	Intermediate Similarity	NPD7146	Approved
0.75	Intermediate Similarity	NPD7521	Approved
0.75	Intermediate Similarity	NPD6409	Approved
0.75	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD7102	Approved
0.75	Intermediate Similarity	NPD5330	Approved
0.7475	Intermediate Similarity	NPD7515	Phase 2
0.7475	Intermediate Similarity	NPD6079	Approved
0.7475	Intermediate Similarity	NPD6411	Approved
0.7447	Intermediate Similarity	NPD3667	Approved
0.7431	Intermediate Similarity	NPD6617	Approved
0.7431	Intermediate Similarity	NPD6869	Approved
0.7431	Intermediate Similarity	NPD6847	Approved
0.7426	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6012	Approved
0.7407	Intermediate Similarity	NPD6013	Approved
0.7407	Intermediate Similarity	NPD6014	Approved
0.7364	Intermediate Similarity	NPD6882	Approved
0.7363	Intermediate Similarity	NPD6117	Approved
0.7347	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6903	Approved
0.7315	Intermediate Similarity	NPD6011	Approved
0.73	Intermediate Similarity	NPD5281	Approved
0.73	Intermediate Similarity	NPD5284	Approved
0.7283	Intermediate Similarity	NPD6116	Phase 1
0.7282	Intermediate Similarity	NPD4755	Approved
0.7273	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6101	Approved
0.7273	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4202	Approved
0.7212	Intermediate Similarity	NPD7638	Approved
0.7204	Intermediate Similarity	NPD6697	Approved
0.7204	Intermediate Similarity	NPD6115	Approved
0.7204	Intermediate Similarity	NPD6114	Approved
0.7204	Intermediate Similarity	NPD6118	Approved
0.7184	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5221	Approved
0.7184	Intermediate Similarity	NPD5222	Approved
0.7158	Intermediate Similarity	NPD4692	Approved
0.7158	Intermediate Similarity	NPD4139	Approved
0.7143	Intermediate Similarity	NPD7640	Approved
0.7143	Intermediate Similarity	NPD5285	Approved
0.7143	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4700	Approved
0.7143	Intermediate Similarity	NPD5286	Approved
0.7143	Intermediate Similarity	NPD4696	Approved
0.7143	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD5279	Phase 3
0.7143	Intermediate Similarity	NPD6098	Approved
0.713	Intermediate Similarity	NPD6008	Approved
0.7129	Intermediate Similarity	NPD6050	Approved
0.7115	Intermediate Similarity	NPD5173	Approved
0.7113	Intermediate Similarity	NPD3668	Phase 3
0.7113	Intermediate Similarity	NPD3133	Approved
0.7113	Intermediate Similarity	NPD3665	Phase 1
0.7113	Intermediate Similarity	NPD3666	Approved
0.71	Intermediate Similarity	NPD6904	Approved
0.71	Intermediate Similarity	NPD6080	Approved
0.71	Intermediate Similarity	NPD6673	Approved
0.71	Intermediate Similarity	NPD4753	Phase 2
0.7069	Intermediate Similarity	NPD6319	Approved
0.703	Intermediate Similarity	NPD5207	Approved
0.703	Intermediate Similarity	NPD5692	Phase 3
0.7027	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3617	Approved
0.7018	Intermediate Similarity	NPD6274	Approved
0.7018	Intermediate Similarity	NPD6868	Approved
0.7009	Intermediate Similarity	NPD7632	Discontinued
0.7009	Intermediate Similarity	NPD5226	Approved
0.7009	Intermediate Similarity	NPD4633	Approved
0.7009	Intermediate Similarity	NPD5225	Approved
0.7009	Intermediate Similarity	NPD5224	Approved
0.7009	Intermediate Similarity	NPD5211	Phase 2
0.7	Intermediate Similarity	NPD8293	Discontinued
0.699	Remote Similarity	NPD6001	Approved
0.6983	Remote Similarity	NPD7101	Approved
0.6983	Remote Similarity	NPD7100	Approved
0.6975	Remote Similarity	NPD7492	Approved
0.6961	Remote Similarity	NPD5694	Approved
0.6957	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5174	Approved
0.6944	Remote Similarity	NPD5175	Approved
0.6942	Remote Similarity	NPD7736	Approved
0.6923	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5210	Approved
0.6923	Remote Similarity	NPD4629	Approved
0.6923	Remote Similarity	NPD6054	Approved
0.6923	Remote Similarity	NPD6059	Approved
0.6917	Remote Similarity	NPD6616	Approved
0.6916	Remote Similarity	NPD5223	Approved
0.6907	Remote Similarity	NPD4221	Approved
0.6907	Remote Similarity	NPD4223	Phase 3
0.6897	Remote Similarity	NPD6335	Approved
0.6893	Remote Similarity	NPD5779	Approved
0.6893	Remote Similarity	NPD5778	Approved
0.6887	Remote Similarity	NPD4225	Approved
0.6881	Remote Similarity	NPD5141	Approved
0.6875	Remote Similarity	NPD4634	Approved
0.6875	Remote Similarity	NPD7525	Registered
0.6869	Remote Similarity	NPD1694	Approved
0.6869	Remote Similarity	NPD5329	Approved
0.6864	Remote Similarity	NPD6909	Approved
0.6864	Remote Similarity	NPD6908	Approved
0.686	Remote Similarity	NPD7078	Approved
0.6842	Remote Similarity	NPD4632	Approved
0.6832	Remote Similarity	NPD5208	Approved
0.6818	Remote Similarity	NPD4767	Approved
0.6818	Remote Similarity	NPD4768	Approved
0.681	Remote Similarity	NPD6317	Approved
0.6807	Remote Similarity	NPD6370	Approved
0.6804	Remote Similarity	NPD5369	Approved
0.68	Remote Similarity	NPD5280	Approved
0.68	Remote Similarity	NPD4694	Approved
0.68	Remote Similarity	NPD5690	Phase 2
0.6796	Remote Similarity	NPD7637	Suspended
0.6796	Remote Similarity	NPD5693	Phase 1
0.6789	Remote Similarity	NPD4754	Approved
0.6786	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4197	Approved
0.6765	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5654	Approved
0.6757	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6412	Phase 2
0.6752	Remote Similarity	NPD6314	Approved
0.6752	Remote Similarity	NPD6313	Approved
0.675	Remote Similarity	NPD8328	Phase 3
0.6739	Remote Similarity	NPD5777	Approved
0.6739	Remote Similarity	NPD6081	Approved
0.6733	Remote Similarity	NPD3573	Approved
0.6723	Remote Similarity	NPD6015	Approved
0.6723	Remote Similarity	NPD6016	Approved
0.6723	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD3702	Approved
0.6702	Remote Similarity	NPD7339	Approved
0.6702	Remote Similarity	NPD6942	Approved
0.6701	Remote Similarity	NPD4748	Discontinued
0.6696	Remote Similarity	NPD4730	Approved
0.6696	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4729	Approved
0.6696	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5959	Approved
0.6634	Remote Similarity	NPD4689	Approved
0.6634	Remote Similarity	NPD4138	Approved
0.6634	Remote Similarity	NPD4693	Phase 3
0.6634	Remote Similarity	NPD4688	Approved
0.6634	Remote Similarity	NPD4690	Approved
0.6634	Remote Similarity	NPD5786	Approved
0.6634	Remote Similarity	NPD5205	Approved
0.6612	Remote Similarity	NPD7604	Phase 2
0.6602	Remote Similarity	NPD6051	Approved
0.6598	Remote Similarity	NPD7645	Phase 2
0.6593	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5360	Phase 3
0.6583	Remote Similarity	NPD5983	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