NPASS Compound

Structure

NPC473514 OpenBabel07101718202D 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 0 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 2 20 2 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 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:	570.36
Volume:	608.107
LogP:	4.622
LogD:	2.499
LogS:	-4.655
# Rotatable Bonds:	9
TPSA:	117.97
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.14
Synthetic Accessibility Score:	5.094
Fsp3:	0.765
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:	-5.567
MDCK Permeability:	1.1537985301401932e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.86

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.082
Plasma Protein Binding (PPB):	94.92953491210938%
Volume Distribution (VD):	0.564
Pgp-substrate:	2.301086664199829%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.353
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.893
CYP2C9-inhibitor:	0.177
CYP2C9-substrate:	0.982
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.07
CYP3A4-substrate:	0.184

ADMET: Excretion

Clearance (CL):	1.696
Half-life (T1/2):	0.631

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.292
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.351
Carcinogencity:	0.15
Eye Corrosion:	0.096
Eye Irritation:	0.438
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC473514

Natural Product ID:	NPC473514
*Common Name:**	3Alpha-Carboxyacetoxy-24-Methylen-23-Oxolanost-8-En-26-Oic Acid
IUPAC Name:	(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-methyl-3-methylidene-4-oxoheptanoic acid
Synonyms:
Standard InCHIKey:	LJDYIANNVNRBHB-DAACNWGDSA-N
Standard InCHI:	InChI=1S/C34H50O7/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/h19,21-22,26-27H,2,9-18H2,1,3-8H3,(H,36,37)(H,39,40)/t19-,21?,22-,26+,27-,32-,33-,34+/m1/s1
SMILES:	OC(=O)CC(=O)O[C@@H]1CC[C@]2([C@H](C1(C)C)CCC1=C2CC[C@]2([C@@]1(C)CC[C@@H]2[C@@H](CC(=O)C(=C)C(C(=O)O)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444416
PubChem CID:	12019184
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]
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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	Activity	>	125.0	ug ml-1	PMID[532759]

☑ 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 NPC473514 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	193
0.1-0.2	1262
0.2-0.3	4943
0.3-0.4	10761
0.4-0.5	11034
0.5-0.6	6428
0.6-0.7	5959
0.7-0.8	1946
0.8-0.85	142
0.85-0.9	26
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9462	High Similarity	NPC473648
0.9362	High Similarity	NPC120708
0.8936	High Similarity	NPC26888
0.8925	High Similarity	NPC474889
0.883	High Similarity	NPC111585
0.883	High Similarity	NPC148414
0.883	High Similarity	NPC175628
0.8812	High Similarity	NPC475494
0.875	High Similarity	NPC159410
0.8737	High Similarity	NPC297265
0.8725	High Similarity	NPC220974
0.8713	High Similarity	NPC96268
0.87	High Similarity	NPC473788
0.87	High Similarity	NPC475558
0.866	High Similarity	NPC184848
0.866	High Similarity	NPC210214
0.866	High Similarity	NPC470016
0.866	High Similarity	NPC69548
0.866	High Similarity	NPC317586
0.8632	High Similarity	NPC471896
0.8617	High Similarity	NPC471724
0.8617	High Similarity	NPC242864
0.8614	High Similarity	NPC159442
0.8571	High Similarity	NPC327788
0.8557	High Similarity	NPC166906
0.8526	High Similarity	NPC474570
0.8454	Intermediate Similarity	NPC107674
0.8454	Intermediate Similarity	NPC141497
0.8454	Intermediate Similarity	NPC170220
0.8431	Intermediate Similarity	NPC470310
0.8411	Intermediate Similarity	NPC472929
0.8404	Intermediate Similarity	NPC55309
0.8404	Intermediate Similarity	NPC28252
0.84	Intermediate Similarity	NPC477813
0.84	Intermediate Similarity	NPC78427
0.84	Intermediate Similarity	NPC16911
0.8384	Intermediate Similarity	NPC13949
0.8384	Intermediate Similarity	NPC305483
0.8384	Intermediate Similarity	NPC328162
0.8384	Intermediate Similarity	NPC95565
0.8384	Intermediate Similarity	NPC96859
0.8365	Intermediate Similarity	NPC91034
0.8351	Intermediate Similarity	NPC23434
0.8351	Intermediate Similarity	NPC471901
0.8351	Intermediate Similarity	NPC212301
0.8351	Intermediate Similarity	NPC86266
0.8351	Intermediate Similarity	NPC110657
0.835	Intermediate Similarity	NPC2436
0.835	Intermediate Similarity	NPC470251
0.835	Intermediate Similarity	NPC216245
0.835	Intermediate Similarity	NPC135854
0.8349	Intermediate Similarity	NPC472934
0.8333	Intermediate Similarity	NPC475921
0.8333	Intermediate Similarity	NPC281702
0.8333	Intermediate Similarity	NPC474704
0.8333	Intermediate Similarity	NPC53222
0.8333	Intermediate Similarity	NPC136289
0.8317	Intermediate Similarity	NPC316964
0.8317	Intermediate Similarity	NPC88198
0.8317	Intermediate Similarity	NPC35751
0.8317	Intermediate Similarity	NPC287676
0.8316	Intermediate Similarity	NPC187376
0.8316	Intermediate Similarity	NPC159046
0.8316	Intermediate Similarity	NPC233836
0.83	Intermediate Similarity	NPC320306
0.83	Intermediate Similarity	NPC108078
0.83	Intermediate Similarity	NPC26413
0.8283	Intermediate Similarity	NPC255809
0.8283	Intermediate Similarity	NPC195715
0.8283	Intermediate Similarity	NPC469599
0.8265	Intermediate Similarity	NPC470224
0.8265	Intermediate Similarity	NPC294263
0.8265	Intermediate Similarity	NPC287118
0.8265	Intermediate Similarity	NPC473690
0.8265	Intermediate Similarity	NPC471902
0.8252	Intermediate Similarity	NPC33973
0.8252	Intermediate Similarity	NPC70967
0.8252	Intermediate Similarity	NPC72151
0.8247	Intermediate Similarity	NPC469400
0.8241	Intermediate Similarity	NPC52634
0.8241	Intermediate Similarity	NPC122056
0.8241	Intermediate Similarity	NPC472926
0.8235	Intermediate Similarity	NPC99411
0.8235	Intermediate Similarity	NPC289148
0.8235	Intermediate Similarity	NPC163963
0.8235	Intermediate Similarity	NPC52899
0.8235	Intermediate Similarity	NPC81530
0.8235	Intermediate Similarity	NPC124211
0.8229	Intermediate Similarity	NPC471722
0.8224	Intermediate Similarity	NPC474315
0.8218	Intermediate Similarity	NPC478056
0.8211	Intermediate Similarity	NPC72133
0.82	Intermediate Similarity	NPC7124
0.82	Intermediate Similarity	NPC328371
0.82	Intermediate Similarity	NPC471153
0.82	Intermediate Similarity	NPC42042
0.8198	Intermediate Similarity	NPC472933
0.819	Intermediate Similarity	NPC472925
0.8182	Intermediate Similarity	NPC473431
0.8182	Intermediate Similarity	NPC473280
0.8182	Intermediate Similarity	NPC472927
0.8182	Intermediate Similarity	NPC78580
0.8182	Intermediate Similarity	NPC471078
0.8182	Intermediate Similarity	NPC473435
0.8182	Intermediate Similarity	NPC23621
0.8182	Intermediate Similarity	NPC470697
0.8182	Intermediate Similarity	NPC47853
0.8182	Intermediate Similarity	NPC49670
0.8182	Intermediate Similarity	NPC184006
0.8173	Intermediate Similarity	NPC98603
0.8165	Intermediate Similarity	NPC67259
0.8165	Intermediate Similarity	NPC147912
0.8163	Intermediate Similarity	NPC160506
0.8163	Intermediate Similarity	NPC250753
0.8163	Intermediate Similarity	NPC475416
0.8155	Intermediate Similarity	NPC293753
0.8155	Intermediate Similarity	NPC88203
0.8155	Intermediate Similarity	NPC76866
0.8155	Intermediate Similarity	NPC22388
0.8155	Intermediate Similarity	NPC304832
0.8155	Intermediate Similarity	NPC148628
0.8155	Intermediate Similarity	NPC246736
0.8155	Intermediate Similarity	NPC286519
0.8155	Intermediate Similarity	NPC320447
0.8155	Intermediate Similarity	NPC234892
0.8155	Intermediate Similarity	NPC214946
0.8155	Intermediate Similarity	NPC56498
0.8148	Intermediate Similarity	NPC69291
0.8144	Intermediate Similarity	NPC31985
0.8144	Intermediate Similarity	NPC77168
0.8144	Intermediate Similarity	NPC102414
0.8144	Intermediate Similarity	NPC84271
0.8144	Intermediate Similarity	NPC54689
0.8144	Intermediate Similarity	NPC1015
0.8137	Intermediate Similarity	NPC144660
0.8137	Intermediate Similarity	NPC475392
0.8137	Intermediate Similarity	NPC327431
0.8137	Intermediate Similarity	NPC307954
0.8137	Intermediate Similarity	NPC476274
0.8137	Intermediate Similarity	NPC474012
0.8137	Intermediate Similarity	NPC299971
0.8137	Intermediate Similarity	NPC476299
0.8137	Intermediate Similarity	NPC476303
0.8137	Intermediate Similarity	NPC475202
0.8137	Intermediate Similarity	NPC157787
0.8137	Intermediate Similarity	NPC475385
0.8131	Intermediate Similarity	NPC197428
0.8125	Intermediate Similarity	NPC142361
0.8125	Intermediate Similarity	NPC167877
0.8125	Intermediate Similarity	NPC96496
0.8125	Intermediate Similarity	NPC474684
0.8119	Intermediate Similarity	NPC43747
0.8119	Intermediate Similarity	NPC226986
0.8119	Intermediate Similarity	NPC141401
0.8119	Intermediate Similarity	NPC23680
0.8119	Intermediate Similarity	NPC89225
0.8113	Intermediate Similarity	NPC295244
0.81	Intermediate Similarity	NPC174948
0.81	Intermediate Similarity	NPC162001
0.81	Intermediate Similarity	NPC88310
0.81	Intermediate Similarity	NPC279974
0.81	Intermediate Similarity	NPC222845
0.81	Intermediate Similarity	NPC263347
0.81	Intermediate Similarity	NPC469995
0.81	Intermediate Similarity	NPC318282
0.81	Intermediate Similarity	NPC48330
0.81	Intermediate Similarity	NPC470229
0.81	Intermediate Similarity	NPC173875
0.81	Intermediate Similarity	NPC23241
0.81	Intermediate Similarity	NPC45324
0.8095	Intermediate Similarity	NPC472935
0.8095	Intermediate Similarity	NPC265127
0.8085	Intermediate Similarity	NPC470015
0.8085	Intermediate Similarity	NPC168188
0.8081	Intermediate Similarity	NPC470375
0.8081	Intermediate Similarity	NPC470254
0.8081	Intermediate Similarity	NPC470376
0.8081	Intermediate Similarity	NPC25750
0.8081	Intermediate Similarity	NPC38232
0.8077	Intermediate Similarity	NPC236390
0.8077	Intermediate Similarity	NPC180204
0.8077	Intermediate Similarity	NPC87927
0.8077	Intermediate Similarity	NPC36321
0.8077	Intermediate Similarity	NPC216114
0.8061	Intermediate Similarity	NPC20388
0.8061	Intermediate Similarity	NPC191684
0.8061	Intermediate Similarity	NPC477147
0.8061	Intermediate Similarity	NPC477149
0.8061	Intermediate Similarity	NPC44240
0.8058	Intermediate Similarity	NPC476240
0.8058	Intermediate Similarity	NPC476223
0.8058	Intermediate Similarity	NPC46848
0.8058	Intermediate Similarity	NPC115899
0.8058	Intermediate Similarity	NPC148279
0.8058	Intermediate Similarity	NPC472924
0.8058	Intermediate Similarity	NPC236585
0.8058	Intermediate Similarity	NPC224720
0.8056	Intermediate Similarity	NPC472928
0.8041	Intermediate Similarity	NPC4309
0.8041	Intermediate Similarity	NPC80335

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 NPC473514 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1640
0.2-0.3	3918
0.3-0.4	2267
0.4-0.5	681
0.5-0.6	205
0.6-0.7	175
0.7-0.8	105
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
0.8646	High Similarity	NPD6399	Phase 3
0.8163	Intermediate Similarity	NPD8035	Phase 2
0.8163	Intermediate Similarity	NPD8034	Phase 2
0.8119	Intermediate Similarity	NPD7902	Approved
0.8056	Intermediate Similarity	NPD6650	Approved
0.8056	Intermediate Similarity	NPD6649	Approved
0.8037	Intermediate Similarity	NPD6372	Approved
0.8037	Intermediate Similarity	NPD6373	Approved
0.8018	Intermediate Similarity	NPD7115	Discovery
0.8	Intermediate Similarity	NPD7748	Approved
0.7944	Intermediate Similarity	NPD6881	Approved
0.7944	Intermediate Similarity	NPD6899	Approved
0.7925	Intermediate Similarity	NPD5739	Approved
0.7925	Intermediate Similarity	NPD7128	Approved
0.7925	Intermediate Similarity	NPD6675	Approved
0.7925	Intermediate Similarity	NPD6402	Approved
0.7921	Intermediate Similarity	NPD5695	Phase 3
0.789	Intermediate Similarity	NPD8130	Phase 1
0.785	Intermediate Similarity	NPD5697	Approved
0.7835	Intermediate Similarity	NPD3618	Phase 1
0.7822	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD7900	Approved
0.7818	Intermediate Similarity	NPD8297	Approved
0.7812	Intermediate Similarity	NPD4786	Approved
0.78	Intermediate Similarity	NPD6079	Approved
0.7798	Intermediate Similarity	NPD7290	Approved
0.7798	Intermediate Similarity	NPD6883	Approved
0.7798	Intermediate Similarity	NPD7102	Approved
0.7778	Intermediate Similarity	NPD7320	Approved
0.7778	Intermediate Similarity	NPD5328	Approved
0.7767	Intermediate Similarity	NPD6083	Phase 2
0.7767	Intermediate Similarity	NPD6084	Phase 2
0.7727	Intermediate Similarity	NPD6869	Approved
0.7727	Intermediate Similarity	NPD6847	Approved
0.7727	Intermediate Similarity	NPD6617	Approved
0.7706	Intermediate Similarity	NPD6013	Approved
0.7706	Intermediate Similarity	NPD6012	Approved
0.7706	Intermediate Similarity	NPD6014	Approved
0.7692	Intermediate Similarity	NPD5696	Approved
0.7685	Intermediate Similarity	NPD5701	Approved
0.7677	Intermediate Similarity	NPD6672	Approved
0.7677	Intermediate Similarity	NPD5737	Approved
0.767	Intermediate Similarity	NPD4697	Phase 3
0.7658	Intermediate Similarity	NPD6882	Approved
0.7653	Intermediate Similarity	NPD7146	Approved
0.7653	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD7521	Approved
0.7653	Intermediate Similarity	NPD7334	Approved
0.7653	Intermediate Similarity	NPD6684	Approved
0.7653	Intermediate Similarity	NPD6409	Approved
0.7653	Intermediate Similarity	NPD5330	Approved
0.7624	Intermediate Similarity	NPD7515	Phase 2
0.7624	Intermediate Similarity	NPD6411	Approved
0.7615	Intermediate Similarity	NPD6011	Approved
0.7604	Intermediate Similarity	NPD3667	Approved
0.7573	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6903	Approved
0.75	Intermediate Similarity	NPD5222	Approved
0.75	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5221	Approved
0.7453	Intermediate Similarity	NPD5286	Approved
0.7453	Intermediate Similarity	NPD5285	Approved
0.7453	Intermediate Similarity	NPD4696	Approved
0.7451	Intermediate Similarity	NPD5281	Approved
0.7451	Intermediate Similarity	NPD5284	Approved
0.7431	Intermediate Similarity	NPD6008	Approved
0.7429	Intermediate Similarity	NPD5173	Approved
0.7429	Intermediate Similarity	NPD4755	Approved
0.7426	Intermediate Similarity	NPD6101	Approved
0.7426	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4202	Approved
0.7358	Intermediate Similarity	NPD7638	Approved
0.7358	Intermediate Similarity	NPD4225	Approved
0.735	Intermediate Similarity	NPD6319	Approved
0.7315	Intermediate Similarity	NPD5226	Approved
0.7315	Intermediate Similarity	NPD5225	Approved
0.7315	Intermediate Similarity	NPD4633	Approved
0.7315	Intermediate Similarity	NPD5224	Approved
0.7315	Intermediate Similarity	NPD5211	Phase 2
0.7304	Intermediate Similarity	NPD6868	Approved
0.7304	Intermediate Similarity	NPD6274	Approved
0.73	Intermediate Similarity	NPD5279	Phase 3
0.729	Intermediate Similarity	NPD7640	Approved
0.729	Intermediate Similarity	NPD4700	Approved
0.729	Intermediate Similarity	NPD7639	Approved
0.7282	Intermediate Similarity	NPD6050	Approved
0.7273	Intermediate Similarity	NPD3666	Approved
0.7273	Intermediate Similarity	NPD3133	Approved
0.7273	Intermediate Similarity	NPD3665	Phase 1
0.7273	Intermediate Similarity	NPD3668	Phase 3
0.7265	Intermediate Similarity	NPD7101	Approved
0.7265	Intermediate Similarity	NPD7100	Approved
0.7255	Intermediate Similarity	NPD4753	Phase 2
0.7255	Intermediate Similarity	NPD6673	Approved
0.7255	Intermediate Similarity	NPD6904	Approved
0.7255	Intermediate Similarity	NPD6080	Approved
0.725	Intermediate Similarity	NPD7492	Approved
0.7248	Intermediate Similarity	NPD5175	Approved
0.7248	Intermediate Similarity	NPD5174	Approved
0.7238	Intermediate Similarity	NPD5210	Approved
0.7238	Intermediate Similarity	NPD4629	Approved
0.7232	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5223	Approved
0.7213	Intermediate Similarity	NPD7736	Approved
0.7203	Intermediate Similarity	NPD6054	Approved
0.719	Intermediate Similarity	NPD6616	Approved
0.7184	Intermediate Similarity	NPD5692	Phase 3
0.7184	Intermediate Similarity	NPD5207	Approved
0.7182	Intermediate Similarity	NPD5141	Approved
0.7179	Intermediate Similarity	NPD6335	Approved
0.7168	Intermediate Similarity	NPD4634	Approved
0.7143	Intermediate Similarity	NPD6001	Approved
0.7131	Intermediate Similarity	NPD8293	Discontinued
0.7131	Intermediate Similarity	NPD7078	Approved
0.713	Intermediate Similarity	NPD4632	Approved
0.7129	Intermediate Similarity	NPD6098	Approved
0.7129	Intermediate Similarity	NPD5690	Phase 2
0.7115	Intermediate Similarity	NPD5694	Approved
0.7094	Intermediate Similarity	NPD6317	Approved
0.7083	Intermediate Similarity	NPD6370	Approved
0.7071	Intermediate Similarity	NPD4223	Phase 3
0.7071	Intermediate Similarity	NPD4221	Approved
0.7059	Intermediate Similarity	NPD3573	Approved
0.7059	Intermediate Similarity	NPD6059	Approved
0.7048	Intermediate Similarity	NPD5778	Approved
0.7048	Intermediate Similarity	NPD5779	Approved
0.7034	Intermediate Similarity	NPD6313	Approved
0.7034	Intermediate Similarity	NPD6314	Approved
0.703	Intermediate Similarity	NPD5329	Approved
0.703	Intermediate Similarity	NPD1694	Approved
0.7019	Intermediate Similarity	NPD5785	Approved
0.7	Intermediate Similarity	NPD6908	Approved
0.7	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4788	Approved
0.7	Intermediate Similarity	NPD6016	Approved
0.7	Intermediate Similarity	NPD6015	Approved
0.7	Intermediate Similarity	NPD6909	Approved
0.6991	Remote Similarity	NPD4730	Approved
0.6991	Remote Similarity	NPD4729	Approved
0.6991	Remote Similarity	NPD5128	Approved
0.699	Remote Similarity	NPD5208	Approved
0.6979	Remote Similarity	NPD6117	Approved
0.697	Remote Similarity	NPD5369	Approved
0.6964	Remote Similarity	NPD4768	Approved
0.6964	Remote Similarity	NPD4767	Approved
0.6961	Remote Similarity	NPD5280	Approved
0.6961	Remote Similarity	NPD4694	Approved
0.6952	Remote Similarity	NPD7637	Suspended
0.6952	Remote Similarity	NPD5693	Phase 1
0.6949	Remote Similarity	NPD6009	Approved
0.6942	Remote Similarity	NPD5988	Approved
0.6937	Remote Similarity	NPD4754	Approved
0.6931	Remote Similarity	NPD4197	Approved
0.6923	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6116	Phase 1
0.6903	Remote Similarity	NPD6412	Phase 2
0.6885	Remote Similarity	NPD8328	Phase 3
0.6885	Remote Similarity	NPD7604	Phase 2
0.6875	Remote Similarity	NPD7339	Approved
0.6875	Remote Similarity	NPD6942	Approved
0.687	Remote Similarity	NPD5250	Approved
0.687	Remote Similarity	NPD5251	Approved
0.687	Remote Similarity	NPD5248	Approved
0.687	Remote Similarity	NPD5249	Phase 3
0.687	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5247	Approved
0.6869	Remote Similarity	NPD7525	Registered
0.6869	Remote Similarity	NPD4695	Discontinued
0.6863	Remote Similarity	NPD5363	Approved
0.686	Remote Similarity	NPD5983	Phase 2
0.6847	Remote Similarity	NPD7632	Discontinued
0.6842	Remote Similarity	NPD5168	Approved
0.6837	Remote Similarity	NPD3617	Approved
0.6837	Remote Similarity	NPD6114	Approved
0.6837	Remote Similarity	NPD6115	Approved
0.6837	Remote Similarity	NPD6697	Approved
0.6837	Remote Similarity	NPD6118	Approved
0.681	Remote Similarity	NPD5217	Approved
0.681	Remote Similarity	NPD5215	Approved
0.681	Remote Similarity	NPD5216	Approved
0.6807	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4692	Approved
0.68	Remote Similarity	NPD4139	Approved
0.6796	Remote Similarity	NPD4138	Approved
0.6796	Remote Similarity	NPD5786	Approved
0.6796	Remote Similarity	NPD4689	Approved
0.6796	Remote Similarity	NPD5205	Approved
0.6796	Remote Similarity	NPD4688	Approved
0.6796	Remote Similarity	NPD4690	Approved
0.6796	Remote Similarity	NPD4693	Phase 3
0.6774	Remote Similarity	NPD6336	Discontinued
0.6771	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5654	Approved
0.6759	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4270	Approved
0.6733	Remote Similarity	NPD4269	Approved
0.6733	Remote Similarity	NPD4752	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