NPASS Compound

Structure

NPC470049 OpenBabel07101719252D 33 36 0 0 1 0 0 0 0 0999 V2000 -3.1653 -5.3212 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 -2.2382 -2.4680 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 -0.5398 -5.6485 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 -1.8781 -4.1622 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 -2.1871 -5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9000 -3.9543 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 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 2.5981 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 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 2 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 5.1962 2.0000 0.0000 O 0 0 0 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 1 20 1 0 0 0 0 2 20 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 9 33 1 0 0 0 0 10 11 1 0 0 0 0 10 25 2 0 0 0 0 11 26 1 0 0 0 0 12 16 1 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 14 27 1 0 0 0 0 15 29 1 0 0 0 0 16 31 1 0 0 0 0 17 30 1 0 0 0 0 18 20 2 0 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 21 3 1 6 0 0 0 21 23 1 0 0 0 0 22 18 1 1 0 0 0 22 33 1 0 0 0 0 23 30 1 6 0 0 0 24 25 1 0 0 0 0 24 29 1 1 0 0 0 25 31 1 0 0 0 0 26 28 1 0 0 0 0 26 29 1 0 0 0 0 27 28 1 0 0 0 0 27 32 1 1 0 0 0 29 6 1 1 0 0 0 30 31 1 6 0 0 0 31 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.4
Volume:	522.814
LogP:	7.658
LogD:	5.536
LogS:	-6.247
# Rotatable Bonds:	5
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.425
Synthetic Accessibility Score:	4.925
Fsp3:	0.871
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.701
MDCK Permeability:	1.0897486390604172e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.896

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.109
Plasma Protein Binding (PPB):	95.58072662353516%
Volume Distribution (VD):	1.653
Pgp-substrate:	2.4504146575927734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.33
CYP2C19-inhibitor:	0.08
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.213
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.849
CYP3A4-substrate:	0.807

ADMET: Excretion

Clearance (CL):	11.207
Half-life (T1/2):	0.012

ADMET: Toxicity

hERG Blockers:	0.659
Human Hepatotoxicity (H-HT):	0.697
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.723
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.701
Carcinogencity:	0.038
Eye Corrosion:	0.02
Eye Irritation:	0.039
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC470049

Natural Product ID:	NPC470049
*Common Name:**	Cornusalterin J
IUPAC Name:	(3S,9R,10R,13S,14S,17S)-17-[(2S,4R)-4-methoxy-6-methylhept-5-en-2-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:	Cornusalterin J
Standard InCHIKey:	CMYFKSGATOJENB-LRTLWCEFSA-N
Standard InCHI:	InChI=1S/C31H52O2/c1-20(2)18-22(33-9)19-21(3)23-12-16-31(8)25-10-11-26-28(4,5)27(32)14-15-29(26,6)24(25)13-17-30(23,31)7/h10,18,21-24,26-27,32H,11-17,19H2,1-9H3/t21-,22-,23-,24-,26?,27-,29+,30-,31+/m0/s1
SMILES:	CC(CC(C=C(C)C)OC)C1CCC2(C1(CCC3C2=CCC4C3(CCC(C4(C)C)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668103
PubChem CID:	53323674
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
NPO19594	Cornus walteri	Species	Cornaceae	Eukaryota	n.a.	stem	n.a.	PMID[21182258]
NPO19594	Cornus walteri	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21182258]
NPO19594	Cornus walteri	Species	Cornaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	25400.0	nM	PMID[544761]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	17830.0	nM	PMID[544761]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	12330.0	nM	PMID[544761]
NPT574	Cell Line	XF498	Homo sapiens	IC50	=	18170.0	nM	PMID[544761]

☑ 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 NPC470049 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	156
0.1-0.2	1338
0.2-0.3	5058
0.3-0.4	15193
0.4-0.5	8600
0.5-0.6	5893
0.6-0.7	4554
0.7-0.8	1514
0.8-0.85	215
0.85-0.9	128
0.9-0.95	40
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9744	High Similarity	NPC470077
0.961	High Similarity	NPC474731
0.961	High Similarity	NPC7505
0.961	High Similarity	NPC474759
0.961	High Similarity	NPC82986
0.961	High Similarity	NPC474683
0.961	High Similarity	NPC474752
0.9375	High Similarity	NPC157257
0.9375	High Similarity	NPC274448
0.9375	High Similarity	NPC266511
0.9367	High Similarity	NPC470558
0.9351	High Similarity	NPC30986
0.9351	High Similarity	NPC209430
0.9211	High Similarity	NPC189883
0.9146	High Similarity	NPC149224
0.9103	High Similarity	NPC1319
0.9103	High Similarity	NPC109546
0.9103	High Similarity	NPC47982
0.9103	High Similarity	NPC143182
0.9103	High Similarity	NPC84694
0.9103	High Similarity	NPC28862
0.9103	High Similarity	NPC81306
0.9091	High Similarity	NPC214570
0.9079	High Similarity	NPC471723
0.9079	High Similarity	NPC141071
0.9079	High Similarity	NPC257347
0.9048	High Similarity	NPC295668
0.9036	High Similarity	NPC471952
0.9012	High Similarity	NPC474047
0.9	High Similarity	NPC296701
0.9	High Similarity	NPC101462
0.9	High Similarity	NPC87489
0.9	High Similarity	NPC304285
0.9	High Similarity	NPC218616
0.9	High Similarity	NPC49964
0.9	High Similarity	NPC202389
0.8987	High Similarity	NPC236112
0.8987	High Similarity	NPC234193
0.8974	High Similarity	NPC167037
0.8974	High Similarity	NPC244385
0.8974	High Similarity	NPC474216
0.8974	High Similarity	NPC6978
0.8974	High Similarity	NPC138621
0.8974	High Similarity	NPC285761
0.8974	High Similarity	NPC473943
0.8974	High Similarity	NPC275910
0.8961	High Similarity	NPC244488
0.8961	High Similarity	NPC240604
0.8961	High Similarity	NPC300324
0.8961	High Similarity	NPC321016
0.8961	High Similarity	NPC134330
0.8961	High Similarity	NPC202642
0.8961	High Similarity	NPC237460
0.8961	High Similarity	NPC46160
0.8961	High Similarity	NPC129165
0.8961	High Similarity	NPC321381
0.8961	High Similarity	NPC73875
0.8961	High Similarity	NPC107059
0.8961	High Similarity	NPC247325
0.8902	High Similarity	NPC318390
0.8889	High Similarity	NPC475789
0.8889	High Similarity	NPC317458
0.8875	High Similarity	NPC264245
0.8875	High Similarity	NPC47761
0.8875	High Similarity	NPC209620
0.8875	High Similarity	NPC474531
0.8875	High Similarity	NPC23852
0.8861	High Similarity	NPC80530
0.8861	High Similarity	NPC273410
0.8846	High Similarity	NPC318495
0.8846	High Similarity	NPC155986
0.8846	High Similarity	NPC198968
0.8831	High Similarity	NPC230301
0.8831	High Similarity	NPC22105
0.8831	High Similarity	NPC136188
0.8831	High Similarity	NPC322353
0.8831	High Similarity	NPC288035
0.8831	High Similarity	NPC285893
0.8831	High Similarity	NPC118508
0.8831	High Similarity	NPC134847
0.8831	High Similarity	NPC121744
0.8831	High Similarity	NPC162742
0.8831	High Similarity	NPC28657
0.8831	High Similarity	NPC304309
0.8795	High Similarity	NPC261266
0.8795	High Similarity	NPC6391
0.878	High Similarity	NPC205845
0.878	High Similarity	NPC231310
0.878	High Similarity	NPC185568
0.8765	High Similarity	NPC50964
0.8765	High Similarity	NPC155521
0.8765	High Similarity	NPC189972
0.8765	High Similarity	NPC30166
0.875	High Similarity	NPC102253
0.875	High Similarity	NPC13554
0.875	High Similarity	NPC236237
0.875	High Similarity	NPC322313
0.875	High Similarity	NPC241290
0.875	High Similarity	NPC209944
0.875	High Similarity	NPC164840
0.8736	High Similarity	NPC144202
0.8736	High Similarity	NPC127718
0.8736	High Similarity	NPC65402
0.8734	High Similarity	NPC477514
0.8734	High Similarity	NPC186191
0.8734	High Similarity	NPC87604
0.8734	High Similarity	NPC205455
0.8734	High Similarity	NPC302041
0.8734	High Similarity	NPC65897
0.8734	High Similarity	NPC85346
0.8734	High Similarity	NPC477522
0.8718	High Similarity	NPC113733
0.8718	High Similarity	NPC470362
0.8701	High Similarity	NPC469534
0.8701	High Similarity	NPC469533
0.8701	High Similarity	NPC469593
0.8675	High Similarity	NPC470360
0.8659	High Similarity	NPC82623
0.8659	High Similarity	NPC134481
0.8659	High Similarity	NPC474634
0.8642	High Similarity	NPC470383
0.8636	High Similarity	NPC8774
0.8625	High Similarity	NPC328714
0.8621	High Similarity	NPC27531
0.8621	High Similarity	NPC307776
0.8608	High Similarity	NPC470711
0.8608	High Similarity	NPC470758
0.8608	High Similarity	NPC34019
0.8608	High Similarity	NPC91594
0.859	High Similarity	NPC185536
0.8588	High Similarity	NPC133588
0.8571	High Similarity	NPC474970
0.8571	High Similarity	NPC474140
0.8571	High Similarity	NPC299068
0.8571	High Similarity	NPC201373
0.8571	High Similarity	NPC125399
0.8571	High Similarity	NPC182717
0.8554	High Similarity	NPC124172
0.8554	High Similarity	NPC209802
0.8554	High Similarity	NPC238485
0.8554	High Similarity	NPC478102
0.8539	High Similarity	NPC98457
0.8539	High Similarity	NPC227583
0.8539	High Similarity	NPC288970
0.8539	High Similarity	NPC12103
0.8539	High Similarity	NPC88009
0.8537	High Similarity	NPC20853
0.8537	High Similarity	NPC248886
0.8537	High Similarity	NPC201852
0.8537	High Similarity	NPC5985
0.8519	High Similarity	NPC26117
0.8519	High Similarity	NPC295131
0.8506	High Similarity	NPC234335
0.85	High Similarity	NPC476314
0.85	High Similarity	NPC307965
0.85	High Similarity	NPC11908
0.85	High Similarity	NPC312328
0.85	High Similarity	NPC18603
0.85	High Similarity	NPC318136
0.85	High Similarity	NPC76931
0.8488	Intermediate Similarity	NPC262858
0.8488	Intermediate Similarity	NPC472240
0.8488	Intermediate Similarity	NPC473647
0.8488	Intermediate Similarity	NPC470361
0.8481	Intermediate Similarity	NPC470749
0.8481	Intermediate Similarity	NPC96319
0.8471	Intermediate Similarity	NPC470620
0.8462	Intermediate Similarity	NPC477138
0.8462	Intermediate Similarity	NPC243342
0.8462	Intermediate Similarity	NPC201048
0.8462	Intermediate Similarity	NPC100334
0.8462	Intermediate Similarity	NPC476366
0.8462	Intermediate Similarity	NPC91858
0.8444	Intermediate Similarity	NPC210337
0.8442	Intermediate Similarity	NPC167706
0.8442	Intermediate Similarity	NPC111234
0.8434	Intermediate Similarity	NPC470384
0.8434	Intermediate Similarity	NPC477818
0.8434	Intermediate Similarity	NPC113978
0.8434	Intermediate Similarity	NPC207013
0.8434	Intermediate Similarity	NPC110778
0.8415	Intermediate Similarity	NPC70927
0.8415	Intermediate Similarity	NPC476646
0.8415	Intermediate Similarity	NPC6707
0.8395	Intermediate Similarity	NPC472463
0.8391	Intermediate Similarity	NPC291484
0.8391	Intermediate Similarity	NPC3345
0.8391	Intermediate Similarity	NPC80561
0.8391	Intermediate Similarity	NPC329596
0.8391	Intermediate Similarity	NPC204188
0.8391	Intermediate Similarity	NPC11216
0.8375	Intermediate Similarity	NPC212241
0.8375	Intermediate Similarity	NPC157996
0.8375	Intermediate Similarity	NPC40394
0.8375	Intermediate Similarity	NPC119355
0.8375	Intermediate Similarity	NPC34177
0.8375	Intermediate Similarity	NPC331618
0.8375	Intermediate Similarity	NPC248830
0.8375	Intermediate Similarity	NPC471798
0.8375	Intermediate Similarity	NPC472805

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 NPC470049 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1512
0.2-0.3	4164
0.3-0.4	2325
0.4-0.5	552
0.5-0.6	168
0.6-0.7	173
0.7-0.8	92
0.8-0.85	8
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8831	High Similarity	NPD6942	Approved
0.8831	High Similarity	NPD7339	Approved
0.875	High Similarity	NPD7525	Registered
0.8481	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD7645	Phase 2
0.8118	Intermediate Similarity	NPD4786	Approved
0.8068	Intermediate Similarity	NPD5328	Approved
0.8046	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6924	Approved
0.8	Intermediate Similarity	NPD6926	Approved
0.7975	Intermediate Similarity	NPD4243	Approved
0.7957	Intermediate Similarity	NPD7638	Approved
0.7931	Intermediate Similarity	NPD3618	Phase 1
0.7889	Intermediate Similarity	NPD6079	Approved
0.7882	Intermediate Similarity	NPD3667	Approved
0.7872	Intermediate Similarity	NPD7640	Approved
0.7872	Intermediate Similarity	NPD7639	Approved
0.7805	Intermediate Similarity	NPD6933	Approved
0.7778	Intermediate Similarity	NPD4785	Approved
0.7778	Intermediate Similarity	NPD4784	Approved
0.775	Intermediate Similarity	NPD7152	Approved
0.775	Intermediate Similarity	NPD7150	Approved
0.775	Intermediate Similarity	NPD7151	Approved
0.7738	Intermediate Similarity	NPD6929	Approved
0.7722	Intermediate Similarity	NPD6923	Approved
0.7722	Intermediate Similarity	NPD6922	Approved
0.7667	Intermediate Similarity	NPD6051	Approved
0.7647	Intermediate Similarity	NPD4748	Discontinued
0.7647	Intermediate Similarity	NPD6930	Phase 2
0.7647	Intermediate Similarity	NPD6931	Approved
0.7625	Intermediate Similarity	NPD7143	Approved
0.7625	Intermediate Similarity	NPD7144	Approved
0.7609	Intermediate Similarity	NPD4202	Approved
0.7586	Intermediate Similarity	NPD6695	Phase 3
0.75	Intermediate Similarity	NPD6925	Approved
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3666	Approved
0.75	Intermediate Similarity	NPD5776	Phase 2
0.747	Intermediate Similarity	NPD8264	Approved
0.747	Intermediate Similarity	NPD4190	Phase 3
0.747	Intermediate Similarity	NPD5275	Approved
0.7442	Intermediate Similarity	NPD7509	Discontinued
0.7442	Intermediate Similarity	NPD7514	Phase 3
0.7419	Intermediate Similarity	NPD6399	Phase 3
0.7416	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7145	Approved
0.7368	Intermediate Similarity	NPD4697	Phase 3
0.7368	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5221	Approved
0.7368	Intermediate Similarity	NPD5222	Approved
0.7356	Intermediate Similarity	NPD6902	Approved
0.7326	Intermediate Similarity	NPD4195	Approved
0.7294	Intermediate Similarity	NPD6932	Approved
0.7292	Intermediate Similarity	NPD4755	Approved
0.7292	Intermediate Similarity	NPD5173	Approved
0.7253	Intermediate Similarity	NPD7750	Discontinued
0.7253	Intermediate Similarity	NPD7524	Approved
0.7245	Intermediate Similarity	NPD4159	Approved
0.7241	Intermediate Similarity	NPD7332	Phase 2
0.7222	Intermediate Similarity	NPD6893	Approved
0.7172	Intermediate Similarity	NPD5211	Phase 2
0.7172	Intermediate Similarity	NPD7632	Discontinued
0.7143	Intermediate Similarity	NPD5285	Approved
0.7143	Intermediate Similarity	NPD4700	Approved
0.7143	Intermediate Similarity	NPD4696	Approved
0.7143	Intermediate Similarity	NPD5279	Phase 3
0.7143	Intermediate Similarity	NPD5286	Approved
0.7129	Intermediate Similarity	NPD5739	Approved
0.7129	Intermediate Similarity	NPD6675	Approved
0.7129	Intermediate Similarity	NPD6402	Approved
0.7129	Intermediate Similarity	NPD7128	Approved
0.7128	Intermediate Similarity	NPD7515	Phase 2
0.7126	Intermediate Similarity	NPD6683	Phase 2
0.7111	Intermediate Similarity	NPD3668	Phase 3
0.7103	Intermediate Similarity	NPD7115	Discovery
0.7097	Intermediate Similarity	NPD4753	Phase 2
0.7079	Intermediate Similarity	NPD4223	Phase 3
0.7079	Intermediate Similarity	NPD4221	Approved
0.7073	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5223	Approved
0.7041	Intermediate Similarity	NPD4225	Approved
0.7041	Intermediate Similarity	NPD5290	Discontinued
0.7033	Intermediate Similarity	NPD5329	Approved
0.703	Intermediate Similarity	NPD5141	Approved
0.7	Intermediate Similarity	NPD5226	Approved
0.7	Intermediate Similarity	NPD5225	Approved
0.7	Intermediate Similarity	NPD4633	Approved
0.7	Intermediate Similarity	NPD5224	Approved
0.699	Remote Similarity	NPD6881	Approved
0.699	Remote Similarity	NPD7320	Approved
0.699	Remote Similarity	NPD6899	Approved
0.6979	Remote Similarity	NPD7748	Approved
0.6966	Remote Similarity	NPD6898	Phase 1
0.6957	Remote Similarity	NPD6409	Approved
0.6957	Remote Similarity	NPD7146	Approved
0.6957	Remote Similarity	NPD7521	Approved
0.6957	Remote Similarity	NPD5330	Approved
0.6957	Remote Similarity	NPD6684	Approved
0.6957	Remote Similarity	NPD7334	Approved
0.6947	Remote Similarity	NPD8035	Phase 2
0.6947	Remote Similarity	NPD8034	Phase 2
0.6947	Remote Similarity	NPD7087	Discontinued
0.6939	Remote Similarity	NPD6084	Phase 2
0.6939	Remote Similarity	NPD6083	Phase 2
0.6931	Remote Similarity	NPD4754	Approved
0.6931	Remote Similarity	NPD5175	Approved
0.6931	Remote Similarity	NPD5174	Approved
0.6923	Remote Similarity	NPD4197	Approved
0.6923	Remote Similarity	NPD6372	Approved
0.6923	Remote Similarity	NPD6373	Approved
0.6893	Remote Similarity	NPD5701	Approved
0.6893	Remote Similarity	NPD5697	Approved
0.6881	Remote Similarity	NPD7327	Approved
0.6881	Remote Similarity	NPD7328	Approved
0.6857	Remote Similarity	NPD6883	Approved
0.6857	Remote Similarity	NPD7102	Approved
0.6857	Remote Similarity	NPD7290	Approved
0.6835	Remote Similarity	NPD368	Approved
0.6827	Remote Similarity	NPD6011	Approved
0.6818	Remote Similarity	NPD7516	Approved
0.6813	Remote Similarity	NPD4788	Approved
0.6809	Remote Similarity	NPD6672	Approved
0.6809	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6903	Approved
0.6809	Remote Similarity	NPD5737	Approved
0.6796	Remote Similarity	NPD4768	Approved
0.6796	Remote Similarity	NPD4767	Approved
0.6792	Remote Similarity	NPD6649	Approved
0.6792	Remote Similarity	NPD6847	Approved
0.6792	Remote Similarity	NPD6617	Approved
0.6792	Remote Similarity	NPD6650	Approved
0.6792	Remote Similarity	NPD6869	Approved
0.6792	Remote Similarity	NPD8130	Phase 1
0.6792	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4787	Phase 1
0.6774	Remote Similarity	NPD4138	Approved
0.6774	Remote Similarity	NPD4688	Approved
0.6774	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5205	Approved
0.6774	Remote Similarity	NPD4693	Phase 3
0.6774	Remote Similarity	NPD4689	Approved
0.6774	Remote Similarity	NPD4690	Approved
0.6771	Remote Similarity	NPD7637	Suspended
0.6768	Remote Similarity	NPD7902	Approved
0.6762	Remote Similarity	NPD6014	Approved
0.6762	Remote Similarity	NPD6013	Approved
0.6762	Remote Similarity	NPD6012	Approved
0.6757	Remote Similarity	NPD8294	Approved
0.6757	Remote Similarity	NPD8377	Approved
0.6735	Remote Similarity	NPD5210	Approved
0.6735	Remote Similarity	NPD4629	Approved
0.6729	Remote Similarity	NPD8297	Approved
0.6729	Remote Similarity	NPD6882	Approved
0.6706	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD8335	Approved
0.6696	Remote Similarity	NPD7503	Approved
0.6696	Remote Similarity	NPD8033	Approved
0.6696	Remote Similarity	NPD8379	Approved
0.6696	Remote Similarity	NPD8380	Approved
0.6696	Remote Similarity	NPD8296	Approved
0.6696	Remote Similarity	NPD8378	Approved
0.6667	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD5168	Approved
0.6632	Remote Similarity	NPD4723	Approved
0.6632	Remote Similarity	NPD4722	Approved
0.6629	Remote Similarity	NPD3617	Approved
0.6598	Remote Similarity	NPD5693	Phase 1
0.6596	Remote Similarity	NPD4623	Approved
0.6596	Remote Similarity	NPD5280	Approved
0.6596	Remote Similarity	NPD5690	Phase 2
0.6596	Remote Similarity	NPD6098	Approved
0.6596	Remote Similarity	NPD4694	Approved
0.6596	Remote Similarity	NPD4519	Discontinued
0.6591	Remote Similarity	NPD6117	Approved
0.6566	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5695	Phase 3
0.6552	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6868	Approved
0.6542	Remote Similarity	NPD5250	Approved
0.6542	Remote Similarity	NPD5251	Approved
0.6542	Remote Similarity	NPD5247	Approved
0.6542	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4634	Approved
0.6542	Remote Similarity	NPD5135	Approved
0.6542	Remote Similarity	NPD5169	Approved
0.6542	Remote Similarity	NPD5249	Phase 3
0.6542	Remote Similarity	NPD5248	Approved
0.6535	Remote Similarity	NPD5696	Approved
0.6522	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6116	Phase 1
0.6514	Remote Similarity	NPD4632	Approved
0.6494	Remote Similarity	NPD342	Phase 1
0.6489	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD1694	Approved

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