NPASS Compound

Structure

CID98442 OpenBabel06191715442D 33 37 0 0 1 0 0 0 0 0999 V2000 -1.8412 -2.1490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4293 -1.8331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0165 4.2511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 1.9474 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6865 -0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8432 0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3729 -0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0429 4.2511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5297 3.4079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6865 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8432 0.4868 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 -4.2162 -1.4605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 5.0944 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0692 4.2511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 28 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 17 29 1 0 0 0 0 18 20 1 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 19 29 1 0 0 0 0 20 26 1 6 0 0 0 21 25 1 0 0 0 0 21 28 1 1 0 0 0 22 28 1 1 0 0 0 22 30 1 0 0 0 0 23 25 1 0 0 0 0 23 31 1 1 0 0 0 24 27 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	505.751
LogP:	6.192
LogD:	4.767
LogS:	-4.444
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.409
Synthetic Accessibility Score:	4.694
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.381
MDCK Permeability:	1.1540062587300781e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.058
30% Bioavailability (F30%):	0.931

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	97.065185546875%
Volume Distribution (VD):	0.818
Pgp-substrate:	3.483316421508789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.303
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.903
CYP2C9-inhibitor:	0.144
CYP2C9-substrate:	0.452
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.205
CYP3A4-substrate:	0.281

ADMET: Excretion

Clearance (CL):	1.917
Half-life (T1/2):	0.194

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.282
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.337
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.32
Carcinogencity:	0.031
Eye Corrosion:	0.188
Eye Irritation:	0.241
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC98442

Natural Product ID:	NPC98442
*Common Name:**	3-Epikatonic Acid
IUPAC Name:	(2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2-carboxylic acid
Synonyms:	3-Epikatonic Acid
Standard InCHIKey:	JZFSMVXQUWRSIW-FWXFQHTDSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-25(2)21-10-13-30(7)22(28(21,5)12-11-23(25)31)9-8-19-20-18-27(4,24(32)33)15-14-26(20,3)16-17-29(19,30)6/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,26+,27+,28-,29+,30+/m0/s1
SMILES:	CC1(C)[C@@H]2CC[C@]3(C)[C@H](CC=C4[C@@H]5C[C@@](C)(CC[C@]5(C)CC[C@@]34C)C(=O)O)[C@@]2(C)CC[C@@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463266
PubChem CID:	10434225
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
NPO26165	Sandoricum indicum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575968]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19618898]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21953622]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[32520551]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26165	Sandoricum indicum	Species	Meliaceae	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	8

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2831	Cell Line	P388/S	Mus musculus	IC50	>	25.0	ug.mL-1	PMID[450460]
NPT168	Cell Line	P388	Mus musculus	IC50	>	25.0	ug.mL-1	PMID[450460]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	150000.0	nM	PMID[450461]
NPT2	Others	Unspecified		IC50	=	50.0	ug.mL-1	PMID[450460]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16620.0	nM	PMID[450461]

☑ 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 NPC98442 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	201
0.1-0.2	1291
0.2-0.3	5131
0.3-0.4	15242
0.4-0.5	8188
0.5-0.6	5273
0.6-0.7	4701
0.7-0.8	2067
0.8-0.85	212
0.85-0.9	136
0.9-0.95	158
0.95-1	97

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC307426
1.0	High Similarity	NPC130577
1.0	High Similarity	NPC293564
1.0	High Similarity	NPC102683
1.0	High Similarity	NPC68160
1.0	High Similarity	NPC88716
1.0	High Similarity	NPC142415
1.0	High Similarity	NPC242468
1.0	High Similarity	NPC171203
1.0	High Similarity	NPC51700
1.0	High Similarity	NPC18064
0.9878	High Similarity	NPC52169
0.9878	High Similarity	NPC40552
0.9878	High Similarity	NPC473242
0.9878	High Similarity	NPC181225
0.9878	High Similarity	NPC474512
0.9878	High Similarity	NPC17733
0.9878	High Similarity	NPC246708
0.9878	High Similarity	NPC470629
0.9878	High Similarity	NPC290690
0.9878	High Similarity	NPC182797
0.9877	High Similarity	NPC72638
0.9759	High Similarity	NPC225585
0.9759	High Similarity	NPC293048
0.9759	High Similarity	NPC270768
0.9759	High Similarity	NPC143232
0.9759	High Similarity	NPC234346
0.9759	High Similarity	NPC64872
0.9759	High Similarity	NPC25906
0.9759	High Similarity	NPC290972
0.9759	High Similarity	NPC198664
0.9759	High Similarity	NPC274330
0.9759	High Similarity	NPC161751
0.9759	High Similarity	NPC130520
0.9759	High Similarity	NPC59263
0.9759	High Similarity	NPC121798
0.9759	High Similarity	NPC263393
0.9759	High Similarity	NPC127689
0.9759	High Similarity	NPC474972
0.9759	High Similarity	NPC61543
0.9759	High Similarity	NPC470588
0.9759	High Similarity	NPC95246
0.9643	High Similarity	NPC210037
0.9643	High Similarity	NPC290614
0.9643	High Similarity	NPC291028
0.9643	High Similarity	NPC130278
0.9643	High Similarity	NPC126369
0.9643	High Similarity	NPC120968
0.9643	High Similarity	NPC111110
0.9643	High Similarity	NPC86372
0.9643	High Similarity	NPC273621
0.9643	High Similarity	NPC227467
0.9643	High Similarity	NPC172361
0.9643	High Similarity	NPC18872
0.9643	High Similarity	NPC477872
0.9643	High Similarity	NPC7260
0.9643	High Similarity	NPC470589
0.9529	High Similarity	NPC52021
0.9529	High Similarity	NPC145067
0.9529	High Similarity	NPC472149
0.9529	High Similarity	NPC324341
0.9529	High Similarity	NPC233455
0.9529	High Similarity	NPC306541
0.9529	High Similarity	NPC966
0.9529	High Similarity	NPC474525
0.9529	High Similarity	NPC187722
0.9529	High Similarity	NPC228784
0.9529	High Similarity	NPC105189
0.9529	High Similarity	NPC65120
0.9529	High Similarity	NPC158030
0.9529	High Similarity	NPC71074
0.9529	High Similarity	NPC288833
0.9529	High Similarity	NPC235884
0.9529	High Similarity	NPC84319
0.9529	High Similarity	NPC282616
0.9529	High Similarity	NPC155120
0.9529	High Similarity	NPC4036
0.9529	High Similarity	NPC25299
0.9529	High Similarity	NPC300351
0.9524	High Similarity	NPC474686
0.9518	High Similarity	NPC71507
0.9512	High Similarity	NPC133954
0.9419	High Similarity	NPC86368
0.9419	High Similarity	NPC63118
0.9419	High Similarity	NPC275809
0.9419	High Similarity	NPC118519
0.9419	High Similarity	NPC474436
0.9419	High Similarity	NPC74855
0.9419	High Similarity	NPC202728
0.9419	High Similarity	NPC272075
0.9419	High Similarity	NPC214756
0.9419	High Similarity	NPC229281
0.9419	High Similarity	NPC307335
0.9419	High Similarity	NPC49776
0.9419	High Similarity	NPC298554
0.9419	High Similarity	NPC136313
0.9419	High Similarity	NPC295643
0.9419	High Similarity	NPC158059
0.9412	High Similarity	NPC46441
0.9412	High Similarity	NPC193750
0.9412	High Similarity	NPC120840
0.9412	High Similarity	NPC113989
0.9412	High Similarity	NPC474728
0.9412	High Similarity	NPC49320
0.9398	High Similarity	NPC475862
0.9398	High Similarity	NPC477579
0.9398	High Similarity	NPC235341
0.9398	High Similarity	NPC95594
0.9398	High Similarity	NPC74363
0.9398	High Similarity	NPC213412
0.939	High Similarity	NPC171789
0.931	High Similarity	NPC145667
0.931	High Similarity	NPC32407
0.931	High Similarity	NPC191412
0.931	High Similarity	NPC222047
0.931	High Similarity	NPC299996
0.931	High Similarity	NPC231063
0.931	High Similarity	NPC88116
0.931	High Similarity	NPC474529
0.931	High Similarity	NPC91010
0.931	High Similarity	NPC282395
0.931	High Similarity	NPC114159
0.931	High Similarity	NPC20235
0.931	High Similarity	NPC263548
0.931	High Similarity	NPC159365
0.931	High Similarity	NPC209868
0.931	High Similarity	NPC6818
0.9302	High Similarity	NPC38754
0.9302	High Similarity	NPC6255
0.9302	High Similarity	NPC470590
0.9302	High Similarity	NPC60755
0.9302	High Similarity	NPC77099
0.9302	High Similarity	NPC475708
0.9302	High Similarity	NPC285184
0.9302	High Similarity	NPC471588
0.9302	High Similarity	NPC301244
0.9294	High Similarity	NPC30522
0.9286	High Similarity	NPC73064
0.9205	High Similarity	NPC139570
0.9205	High Similarity	NPC148523
0.9205	High Similarity	NPC474727
0.9205	High Similarity	NPC198245
0.9205	High Similarity	NPC96916
0.9205	High Similarity	NPC473240
0.9195	High Similarity	NPC133579
0.9195	High Similarity	NPC474806
0.9195	High Similarity	NPC118490
0.9167	High Similarity	NPC9892
0.9167	High Similarity	NPC329943
0.9167	High Similarity	NPC325594
0.9167	High Similarity	NPC73038
0.9167	High Similarity	NPC91525
0.9167	High Similarity	NPC10005
0.9157	High Similarity	NPC180834
0.9101	High Similarity	NPC307282
0.9101	High Similarity	NPC132824
0.9101	High Similarity	NPC173744
0.9101	High Similarity	NPC305464
0.9101	High Similarity	NPC98874
0.9101	High Similarity	NPC230151
0.9101	High Similarity	NPC25848
0.9101	High Similarity	NPC204961
0.9101	High Similarity	NPC476327
0.9101	High Similarity	NPC157113
0.9101	High Similarity	NPC19376
0.9101	High Similarity	NPC476318
0.9101	High Similarity	NPC207922
0.9101	High Similarity	NPC73004
0.9101	High Similarity	NPC62516
0.9101	High Similarity	NPC201657
0.9101	High Similarity	NPC259733
0.9101	High Similarity	NPC327179
0.9101	High Similarity	NPC158371
0.9101	High Similarity	NPC116457
0.9091	High Similarity	NPC78580
0.9091	High Similarity	NPC23621
0.9091	High Similarity	NPC80365
0.9091	High Similarity	NPC60692
0.9091	High Similarity	NPC188102
0.9091	High Similarity	NPC184006
0.9091	High Similarity	NPC87095
0.9091	High Similarity	NPC296164
0.9091	High Similarity	NPC74751
0.907	High Similarity	NPC69627
0.907	High Similarity	NPC281524
0.9059	High Similarity	NPC173089
0.9059	High Similarity	NPC46912
0.9059	High Similarity	NPC474684
0.9059	High Similarity	NPC142361
0.9059	High Similarity	NPC162107
0.9059	High Similarity	NPC158141
0.9048	High Similarity	NPC191965
0.9024	High Similarity	NPC274050
0.9024	High Similarity	NPC162632
0.9024	High Similarity	NPC3915
0.9024	High Similarity	NPC267691
0.9024	High Similarity	NPC263272
0.9024	High Similarity	NPC473420
0.9012	High Similarity	NPC16394
0.9	High Similarity	NPC476879

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 NPC98442 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1681
0.2-0.3	3917
0.3-0.4	2260
0.4-0.5	655
0.5-0.6	193
0.6-0.7	200
0.7-0.8	56
0.8-0.85	1
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9529	High Similarity	NPD7515	Phase 2
0.9091	High Similarity	NPD7748	Approved
0.8824	High Similarity	NPD7520	Clinical (unspecified phase)
0.8791	High Similarity	NPD7902	Approved
0.8554	High Similarity	NPD7645	Phase 2
0.8462	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7900	Approved
0.8295	Intermediate Similarity	NPD3618	Phase 1
0.8276	Intermediate Similarity	NPD4786	Approved
0.8256	Intermediate Similarity	NPD3667	Approved
0.8222	Intermediate Similarity	NPD5328	Approved
0.8043	Intermediate Similarity	NPD8035	Phase 2
0.8043	Intermediate Similarity	NPD6079	Approved
0.8043	Intermediate Similarity	NPD8034	Phase 2
0.7957	Intermediate Similarity	NPD6399	Phase 3
0.7912	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD3133	Approved
0.7865	Intermediate Similarity	NPD3666	Approved
0.7865	Intermediate Similarity	NPD3665	Phase 1
0.7826	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD4202	Approved
0.7732	Intermediate Similarity	NPD7638	Approved
0.7692	Intermediate Similarity	NPD5330	Approved
0.7692	Intermediate Similarity	NPD6684	Approved
0.7692	Intermediate Similarity	NPD7146	Approved
0.7692	Intermediate Similarity	NPD6409	Approved
0.7692	Intermediate Similarity	NPD7521	Approved
0.7692	Intermediate Similarity	NPD7334	Approved
0.7653	Intermediate Similarity	NPD7640	Approved
0.7653	Intermediate Similarity	NPD7639	Approved
0.7624	Intermediate Similarity	NPD5739	Approved
0.7624	Intermediate Similarity	NPD7128	Approved
0.7624	Intermediate Similarity	NPD6675	Approved
0.7624	Intermediate Similarity	NPD6402	Approved
0.7614	Intermediate Similarity	NPD7525	Registered
0.7609	Intermediate Similarity	NPD3573	Approved
0.7558	Intermediate Similarity	NPD6117	Approved
0.7529	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD6903	Approved
0.7526	Intermediate Similarity	NPD4697	Phase 3
0.7526	Intermediate Similarity	NPD5221	Approved
0.7526	Intermediate Similarity	NPD5222	Approved
0.7526	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD6881	Approved
0.7476	Intermediate Similarity	NPD6899	Approved
0.7476	Intermediate Similarity	NPD7320	Approved
0.7474	Intermediate Similarity	NPD6411	Approved
0.7473	Intermediate Similarity	NPD3668	Phase 3
0.7471	Intermediate Similarity	NPD6116	Phase 1
0.7449	Intermediate Similarity	NPD6084	Phase 2
0.7449	Intermediate Similarity	NPD5173	Approved
0.7449	Intermediate Similarity	NPD6083	Phase 2
0.7449	Intermediate Similarity	NPD4755	Approved
0.7442	Intermediate Similarity	NPD7339	Approved
0.7442	Intermediate Similarity	NPD6942	Approved
0.7404	Intermediate Similarity	NPD6372	Approved
0.7404	Intermediate Similarity	NPD6373	Approved
0.7386	Intermediate Similarity	NPD6115	Approved
0.7386	Intermediate Similarity	NPD6118	Approved
0.7386	Intermediate Similarity	NPD6114	Approved
0.7386	Intermediate Similarity	NPD6697	Approved
0.7379	Intermediate Similarity	NPD5701	Approved
0.7379	Intermediate Similarity	NPD5697	Approved
0.7356	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7614	Phase 1
0.734	Intermediate Similarity	NPD6672	Approved
0.734	Intermediate Similarity	NPD5737	Approved
0.7333	Intermediate Similarity	NPD7290	Approved
0.7333	Intermediate Similarity	NPD7102	Approved
0.7333	Intermediate Similarity	NPD6883	Approved
0.7312	Intermediate Similarity	NPD5279	Phase 3
0.7308	Intermediate Similarity	NPD6011	Approved
0.73	Intermediate Similarity	NPD5286	Approved
0.73	Intermediate Similarity	NPD4700	Approved
0.73	Intermediate Similarity	NPD4696	Approved
0.73	Intermediate Similarity	NPD5285	Approved
0.7264	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6650	Approved
0.7264	Intermediate Similarity	NPD6869	Approved
0.7264	Intermediate Similarity	NPD6649	Approved
0.7264	Intermediate Similarity	NPD6847	Approved
0.7264	Intermediate Similarity	NPD8130	Phase 1
0.7264	Intermediate Similarity	NPD6617	Approved
0.7263	Intermediate Similarity	NPD4753	Phase 2
0.7263	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6101	Approved
0.7253	Intermediate Similarity	NPD4223	Phase 3
0.7253	Intermediate Similarity	NPD4221	Approved
0.7238	Intermediate Similarity	NPD6014	Approved
0.7238	Intermediate Similarity	NPD6013	Approved
0.7238	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6012	Approved
0.7228	Intermediate Similarity	NPD5223	Approved
0.7222	Intermediate Similarity	NPD4695	Discontinued
0.7204	Intermediate Similarity	NPD5329	Approved
0.7196	Intermediate Similarity	NPD8297	Approved
0.7196	Intermediate Similarity	NPD6882	Approved
0.7174	Intermediate Similarity	NPD4788	Approved
0.7168	Intermediate Similarity	NPD8328	Phase 3
0.7157	Intermediate Similarity	NPD5225	Approved
0.7157	Intermediate Similarity	NPD5224	Approved
0.7157	Intermediate Similarity	NPD5211	Phase 2
0.7157	Intermediate Similarity	NPD4633	Approved
0.7157	Intermediate Similarity	NPD5226	Approved
0.7128	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6098	Approved
0.7097	Intermediate Similarity	NPD4197	Approved
0.7093	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7115	Discovery
0.7091	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4754	Approved
0.7087	Intermediate Similarity	NPD5175	Approved
0.7087	Intermediate Similarity	NPD5174	Approved
0.7071	Intermediate Similarity	NPD5695	Phase 3
0.7071	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5696	Approved
0.7019	Intermediate Similarity	NPD5141	Approved
0.7	Intermediate Similarity	NPD7732	Phase 3
0.7	Intermediate Similarity	NPD3617	Approved
0.7	Intermediate Similarity	NPD6868	Approved
0.699	Remote Similarity	NPD7632	Discontinued
0.6972	Remote Similarity	NPD4632	Approved
0.6952	Remote Similarity	NPD4767	Approved
0.6952	Remote Similarity	NPD4768	Approved
0.6947	Remote Similarity	NPD4623	Approved
0.6947	Remote Similarity	NPD4693	Phase 3
0.6947	Remote Similarity	NPD4138	Approved
0.6947	Remote Similarity	NPD4519	Discontinued
0.6947	Remote Similarity	NPD4689	Approved
0.6947	Remote Similarity	NPD4690	Approved
0.6947	Remote Similarity	NPD5205	Approved
0.6947	Remote Similarity	NPD4688	Approved
0.6939	Remote Similarity	NPD5281	Approved
0.6939	Remote Similarity	NPD5284	Approved
0.6907	Remote Similarity	NPD6673	Approved
0.6907	Remote Similarity	NPD6080	Approved
0.6907	Remote Similarity	NPD6904	Approved
0.69	Remote Similarity	NPD5210	Approved
0.69	Remote Similarity	NPD4629	Approved
0.6887	Remote Similarity	NPD6412	Phase 2
0.6882	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6335	Approved
0.6869	Remote Similarity	NPD5778	Approved
0.6869	Remote Similarity	NPD5779	Approved
0.6863	Remote Similarity	NPD4225	Approved
0.6854	Remote Similarity	NPD3703	Phase 2
0.6847	Remote Similarity	NPD6274	Approved
0.6842	Remote Similarity	NPD1694	Approved
0.6822	Remote Similarity	NPD5168	Approved
0.6822	Remote Similarity	NPD4729	Approved
0.6822	Remote Similarity	NPD5128	Approved
0.6822	Remote Similarity	NPD4730	Approved
0.6814	Remote Similarity	NPD7101	Approved
0.6814	Remote Similarity	NPD7100	Approved
0.6813	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5208	Approved
0.68	Remote Similarity	NPD6001	Approved
0.6792	Remote Similarity	NPD6008	Approved
0.6786	Remote Similarity	NPD6009	Approved
0.6786	Remote Similarity	NPD6317	Approved
0.6782	Remote Similarity	NPD4244	Approved
0.6782	Remote Similarity	NPD4245	Approved
0.6771	Remote Similarity	NPD5690	Phase 2
0.6771	Remote Similarity	NPD5280	Approved
0.6771	Remote Similarity	NPD4694	Approved
0.6759	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6926	Approved
0.6742	Remote Similarity	NPD6924	Approved
0.6726	Remote Similarity	NPD6313	Approved
0.6726	Remote Similarity	NPD6314	Approved
0.6706	Remote Similarity	NPD4224	Phase 2
0.6705	Remote Similarity	NPD4243	Approved
0.6697	Remote Similarity	NPD5251	Approved
0.6697	Remote Similarity	NPD5248	Approved
0.6697	Remote Similarity	NPD5249	Phase 3
0.6697	Remote Similarity	NPD4634	Approved
0.6697	Remote Similarity	NPD5247	Approved
0.6697	Remote Similarity	NPD5250	Approved
0.6697	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5135	Approved
0.6697	Remote Similarity	NPD5169	Approved
0.6696	Remote Similarity	NPD6909	Approved
0.6696	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD4137	Phase 3
0.6667	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD3698	Phase 2
0.6667	Remote Similarity	NPD8264	Approved
0.6639	Remote Similarity	NPD7736	Approved
0.6636	Remote Similarity	NPD5216	Approved
0.6636	Remote Similarity	NPD5217	Approved
0.6636	Remote Similarity	NPD5127	Approved
0.6636	Remote Similarity	NPD5215	Approved
0.661	Remote Similarity	NPD7507	Approved
0.6609	Remote Similarity	NPD6319	Approved
0.66	Remote Similarity	NPD5693	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