NPASS Compound

Structure

NPC472488 OpenBabel07101718182D 22 25 0 0 1 0 0 0 0 0999 V2000 0.4238 2.3837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7472 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2472 -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 -0.6236 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.4402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 -0.7201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.7201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1866 1.5291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0672 0.3849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8977 1.5031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1866 -0.0889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6236 0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6236 0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4638 0.6021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 0.0000 0.0000 C 0 0 0 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 1.8886 1.3689 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5201 0.4236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7988 1.7832 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 12 20 1 0 0 0 0 13 16 2 0 0 0 0 14 11 1 1 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 1 0 0 0 16 19 1 0 0 0 0 17 21 2 0 0 0 0 19 4 1 1 0 0 0 20 22 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.21
Volume:	329.921
LogP:	3.974
LogD:	3.618
LogS:	-5.524
# Rotatable Bonds:	0
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.681
Synthetic Accessibility Score:	5.296
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.866
MDCK Permeability:	2.0536106603685766e-05
Pgp-inhibitor:	0.39
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.13
Plasma Protein Binding (PPB):	95.09076690673828%
Volume Distribution (VD):	0.964
Pgp-substrate:	4.50118350982666%

ADMET: Metabolism

CYP1A2-inhibitor:	0.273
CYP1A2-substrate:	0.635
CYP2C19-inhibitor:	0.538
CYP2C19-substrate:	0.851
CYP2C9-inhibitor:	0.729
CYP2C9-substrate:	0.677
CYP2D6-inhibitor:	0.103
CYP2D6-substrate:	0.4
CYP3A4-inhibitor:	0.447
CYP3A4-substrate:	0.417

ADMET: Excretion

Clearance (CL):	2.811
Half-life (T1/2):	0.077

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.421
Drug-inuced Liver Injury (DILI):	0.15
AMES Toxicity:	0.133
Rat Oral Acute Toxicity:	0.098
Maximum Recommended Daily Dose:	0.902
Skin Sensitization:	0.656
Carcinogencity:	0.163
Eye Corrosion:	0.012
Eye Irritation:	0.128
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC472488

Natural Product ID:	NPC472488
*Common Name:**	CHRNFZZARNTWCF-KQEPKPNTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CHRNFZZARNTWCF-KQEPKPNTSA-N
Standard InCHI:	InChI=1S/C20H28O2/c1-12-17(21)14-11-20(12,22)10-13-6-7-15-18(2,3)8-5-9-19(15,4)16(13)14/h14-15,22H,1,5-11H2,2-4H3/t14-,15+,19+,20+/m0/s1
SMILES:	CC1(CCCC2(C1CCC3=C2C4CC(C3)(C(=C)C4=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426496
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001670] Tertiary alcohols

*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
NPO32442	jungermannia fauriana	Species	Jungermanniaceae	Eukaryota	n.a.	Guangxi Zhuang Autonomous Region, China	n.a.	PMID[25856683]

☑ 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	14

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2410	Cell Line	NCI-H1299	Homo sapiens	IC50	=	2600.0	nM	PMID[537292]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	2300.0	nM	PMID[537292]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	2200.0	nM	PMID[537292]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	3200.0	nM	PMID[537292]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	2800.0	nM	PMID[537292]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	3400.0	nM	PMID[537292]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2900.0	nM	PMID[537292]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2300.0	nM	PMID[537292]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1900.0	nM	PMID[537292]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1600.0	nM	PMID[537292]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2700.0	nM	PMID[537292]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2400.0	nM	PMID[537292]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2200.0	nM	PMID[537292]
NPT27	Others	Unspecified		IC50	=	6300.0	nM	PMID[537292]

☑ 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 NPC472488 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	154
0.1-0.2	1340
0.2-0.3	6503
0.3-0.4	15031
0.4-0.5	8594
0.5-0.6	6740
0.6-0.7	3494
0.7-0.8	806
0.8-0.85	23
0.85-0.9	8
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9639	High Similarity	NPC472489
0.9512	High Similarity	NPC472479
0.9176	High Similarity	NPC472477
0.9176	High Similarity	NPC472475
0.9146	High Similarity	NPC472492
0.907	High Similarity	NPC472476
0.8824	High Similarity	NPC472491
0.8824	High Similarity	NPC472494
0.881	High Similarity	NPC472480
0.8721	High Similarity	NPC472493
0.8506	High Similarity	NPC472482
0.8506	High Similarity	NPC472484
0.8506	High Similarity	NPC472481
0.8409	Intermediate Similarity	NPC472483
0.8409	Intermediate Similarity	NPC471724
0.8214	Intermediate Similarity	NPC472490
0.8193	Intermediate Similarity	NPC266193
0.8193	Intermediate Similarity	NPC257666
0.814	Intermediate Similarity	NPC193347
0.8118	Intermediate Similarity	NPC469637
0.8118	Intermediate Similarity	NPC476809
0.8111	Intermediate Similarity	NPC472971
0.8111	Intermediate Similarity	NPC472970
0.8095	Intermediate Similarity	NPC207772
0.8065	Intermediate Similarity	NPC472485
0.8023	Intermediate Similarity	NPC150506
0.8	Intermediate Similarity	NPC471791
0.8	Intermediate Similarity	NPC328313
0.8	Intermediate Similarity	NPC170394
0.8	Intermediate Similarity	NPC72397
0.8	Intermediate Similarity	NPC58271
0.8	Intermediate Similarity	NPC471722
0.8	Intermediate Similarity	NPC48107
0.8	Intermediate Similarity	NPC471793
0.7979	Intermediate Similarity	NPC117133
0.7978	Intermediate Similarity	NPC472974
0.7978	Intermediate Similarity	NPC72133
0.7955	Intermediate Similarity	NPC144258
0.7938	Intermediate Similarity	NPC473424
0.7935	Intermediate Similarity	NPC73457
0.7935	Intermediate Similarity	NPC475806
0.7935	Intermediate Similarity	NPC233116
0.7935	Intermediate Similarity	NPC204341
0.7935	Intermediate Similarity	NPC63748
0.7931	Intermediate Similarity	NPC260956
0.7912	Intermediate Similarity	NPC119416
0.7912	Intermediate Similarity	NPC309603
0.7912	Intermediate Similarity	NPC473999
0.7912	Intermediate Similarity	NPC262043
0.7907	Intermediate Similarity	NPC108955
0.7907	Intermediate Similarity	NPC472478
0.7889	Intermediate Similarity	NPC165895
0.7889	Intermediate Similarity	NPC136948
0.7889	Intermediate Similarity	NPC471792
0.7882	Intermediate Similarity	NPC476808
0.7882	Intermediate Similarity	NPC275494
0.7882	Intermediate Similarity	NPC19443
0.7882	Intermediate Similarity	NPC471409
0.7872	Intermediate Similarity	NPC271195
0.7872	Intermediate Similarity	NPC259286
0.7872	Intermediate Similarity	NPC197158
0.7872	Intermediate Similarity	NPC471624
0.7865	Intermediate Similarity	NPC102292
0.7865	Intermediate Similarity	NPC474083
0.7857	Intermediate Similarity	NPC92080
0.7857	Intermediate Similarity	NPC76966
0.7857	Intermediate Similarity	NPC186554
0.7857	Intermediate Similarity	NPC472305
0.7849	Intermediate Similarity	NPC474807
0.7849	Intermediate Similarity	NPC134826
0.7849	Intermediate Similarity	NPC243866
0.7849	Intermediate Similarity	NPC109305
0.7849	Intermediate Similarity	NPC69454
0.7841	Intermediate Similarity	NPC470015
0.7841	Intermediate Similarity	NPC471036
0.7841	Intermediate Similarity	NPC291320
0.7841	Intermediate Similarity	NPC477373
0.7841	Intermediate Similarity	NPC168188
0.7835	Intermediate Similarity	NPC473514
0.7826	Intermediate Similarity	NPC69622
0.7826	Intermediate Similarity	NPC48010
0.7826	Intermediate Similarity	NPC191684
0.7826	Intermediate Similarity	NPC469400
0.7816	Intermediate Similarity	NPC201912
0.7816	Intermediate Similarity	NPC116797
0.7816	Intermediate Similarity	NPC473217
0.7816	Intermediate Similarity	NPC55869
0.7816	Intermediate Similarity	NPC38350
0.7816	Intermediate Similarity	NPC164210
0.7805	Intermediate Similarity	NPC84790
0.7805	Intermediate Similarity	NPC144627
0.7802	Intermediate Similarity	NPC143767
0.7802	Intermediate Similarity	NPC474677
0.7802	Intermediate Similarity	NPC53911
0.7802	Intermediate Similarity	NPC131470
0.7791	Intermediate Similarity	NPC215843
0.7791	Intermediate Similarity	NPC7232
0.7789	Intermediate Similarity	NPC249954
0.7778	Intermediate Similarity	NPC222613
0.7778	Intermediate Similarity	NPC194417
0.7778	Intermediate Similarity	NPC145879
0.7778	Intermediate Similarity	NPC469994
0.7778	Intermediate Similarity	NPC475022
0.7778	Intermediate Similarity	NPC31564
0.7778	Intermediate Similarity	NPC474778
0.7778	Intermediate Similarity	NPC474732
0.7778	Intermediate Similarity	NPC474733
0.7778	Intermediate Similarity	NPC118648
0.7766	Intermediate Similarity	NPC8993
0.7765	Intermediate Similarity	NPC34110
0.7753	Intermediate Similarity	NPC59453
0.7753	Intermediate Similarity	NPC473246
0.7753	Intermediate Similarity	NPC221758
0.7742	Intermediate Similarity	NPC473998
0.7732	Intermediate Similarity	NPC154072
0.7727	Intermediate Similarity	NPC46881
0.7727	Intermediate Similarity	NPC151519
0.7723	Intermediate Similarity	NPC65941
0.7717	Intermediate Similarity	NPC86319
0.7717	Intermediate Similarity	NPC2983
0.7717	Intermediate Similarity	NPC275740
0.7717	Intermediate Similarity	NPC76879
0.7711	Intermediate Similarity	NPC247586
0.7708	Intermediate Similarity	NPC320306
0.7701	Intermediate Similarity	NPC45495
0.7692	Intermediate Similarity	NPC272039
0.7692	Intermediate Similarity	NPC475740
0.7692	Intermediate Similarity	NPC136548
0.7692	Intermediate Similarity	NPC138756
0.7692	Intermediate Similarity	NPC220930
0.7692	Intermediate Similarity	NPC58063
0.7684	Intermediate Similarity	NPC297199
0.7684	Intermediate Similarity	NPC472932
0.7677	Intermediate Similarity	NPC311612
0.7677	Intermediate Similarity	NPC111323
0.7677	Intermediate Similarity	NPC159442
0.7674	Intermediate Similarity	NPC189485
0.7674	Intermediate Similarity	NPC30321
0.7674	Intermediate Similarity	NPC178852
0.7667	Intermediate Similarity	NPC179006
0.7667	Intermediate Similarity	NPC123319
0.7667	Intermediate Similarity	NPC190704
0.7667	Intermediate Similarity	NPC29447
0.7667	Intermediate Similarity	NPC471224
0.7667	Intermediate Similarity	NPC474853
0.7667	Intermediate Similarity	NPC311702
0.7667	Intermediate Similarity	NPC471034
0.7667	Intermediate Similarity	NPC474218
0.7667	Intermediate Similarity	NPC469948
0.7667	Intermediate Similarity	NPC94531
0.766	Intermediate Similarity	NPC472942
0.766	Intermediate Similarity	NPC250575
0.766	Intermediate Similarity	NPC474736
0.7653	Intermediate Similarity	NPC81530
0.7647	Intermediate Similarity	NPC151622
0.7647	Intermediate Similarity	NPC7629
0.764	Intermediate Similarity	NPC69279
0.764	Intermediate Similarity	NPC83569
0.764	Intermediate Similarity	NPC477852
0.764	Intermediate Similarity	NPC49019
0.7634	Intermediate Similarity	NPC80401
0.7634	Intermediate Similarity	NPC149761
0.7634	Intermediate Similarity	NPC183283
0.7634	Intermediate Similarity	NPC261994
0.7634	Intermediate Similarity	NPC470378
0.7634	Intermediate Similarity	NPC180849
0.7629	Intermediate Similarity	NPC186810
0.7629	Intermediate Similarity	NPC166745
0.7629	Intermediate Similarity	NPC103051
0.7629	Intermediate Similarity	NPC197386
0.7629	Intermediate Similarity	NPC235464
0.7624	Intermediate Similarity	NPC472925
0.7614	Intermediate Similarity	NPC477372
0.7614	Intermediate Similarity	NPC226068
0.7614	Intermediate Similarity	NPC14151
0.7614	Intermediate Similarity	NPC147066
0.7609	Intermediate Similarity	NPC242864
0.7609	Intermediate Similarity	NPC328539
0.7604	Intermediate Similarity	NPC155676
0.7604	Intermediate Similarity	NPC95565
0.7604	Intermediate Similarity	NPC471463
0.76	Intermediate Similarity	NPC96268
0.7586	Intermediate Similarity	NPC477371
0.7582	Intermediate Similarity	NPC55309
0.7582	Intermediate Similarity	NPC20688
0.7582	Intermediate Similarity	NPC28252
0.7582	Intermediate Similarity	NPC470955
0.7582	Intermediate Similarity	NPC89077
0.7582	Intermediate Similarity	NPC94755
0.7582	Intermediate Similarity	NPC51014
0.7579	Intermediate Similarity	NPC166906
0.7579	Intermediate Similarity	NPC292793
0.7576	Intermediate Similarity	NPC87351
0.7576	Intermediate Similarity	NPC136289
0.7576	Intermediate Similarity	NPC293753
0.7576	Intermediate Similarity	NPC477915
0.7558	Intermediate Similarity	NPC97377
0.7558	Intermediate Similarity	NPC106078
0.7558	Intermediate Similarity	NPC471035
0.7558	Intermediate Similarity	NPC212661

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 NPC472488 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1801
0.2-0.3	4264
0.3-0.4	2042
0.4-0.5	482
0.5-0.6	166
0.6-0.7	180
0.7-0.8	50
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8391	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5690	Phase 2
0.814	Intermediate Similarity	NPD4221	Approved
0.814	Intermediate Similarity	NPD4223	Phase 3
0.8023	Intermediate Similarity	NPD4139	Approved
0.8023	Intermediate Similarity	NPD4692	Approved
0.7978	Intermediate Similarity	NPD4694	Approved
0.7978	Intermediate Similarity	NPD5280	Approved
0.7955	Intermediate Similarity	NPD4197	Approved
0.7865	Intermediate Similarity	NPD5329	Approved
0.7778	Intermediate Similarity	NPD4138	Approved
0.7778	Intermediate Similarity	NPD3618	Phase 1
0.7778	Intermediate Similarity	NPD4688	Approved
0.7778	Intermediate Similarity	NPD5205	Approved
0.7778	Intermediate Similarity	NPD4690	Approved
0.7778	Intermediate Similarity	NPD4689	Approved
0.7778	Intermediate Similarity	NPD4693	Phase 3
0.7753	Intermediate Similarity	NPD4786	Approved
0.7742	Intermediate Similarity	NPD5281	Approved
0.7742	Intermediate Similarity	NPD5284	Approved
0.7727	Intermediate Similarity	NPD3667	Approved
0.7674	Intermediate Similarity	NPD3617	Approved
0.766	Intermediate Similarity	NPD4202	Approved
0.7586	Intermediate Similarity	NPD4195	Approved
0.7582	Intermediate Similarity	NPD4623	Approved
0.7582	Intermediate Similarity	NPD4519	Discontinued
0.7576	Intermediate Similarity	NPD5211	Phase 2
0.7556	Intermediate Similarity	NPD3665	Phase 1
0.7556	Intermediate Similarity	NPD3133	Approved
0.7556	Intermediate Similarity	NPD3666	Approved
0.7553	Intermediate Similarity	NPD6079	Approved
0.7527	Intermediate Similarity	NPD5328	Approved
0.7527	Intermediate Similarity	NPD4753	Phase 2
0.75	Intermediate Similarity	NPD4629	Approved
0.75	Intermediate Similarity	NPD4695	Discontinued
0.75	Intermediate Similarity	NPD5210	Approved
0.7474	Intermediate Similarity	NPD5133	Approved
0.7447	Intermediate Similarity	NPD4096	Approved
0.7444	Intermediate Similarity	NPD4788	Approved
0.7426	Intermediate Similarity	NPD5141	Approved
0.7419	Intermediate Similarity	NPD4518	Approved
0.7391	Intermediate Similarity	NPD5279	Phase 3
0.7374	Intermediate Similarity	NPD5285	Approved
0.7374	Intermediate Similarity	NPD5286	Approved
0.7374	Intermediate Similarity	NPD4696	Approved
0.7347	Intermediate Similarity	NPD4755	Approved
0.732	Intermediate Similarity	NPD5695	Phase 3
0.73	Intermediate Similarity	NPD5223	Approved
0.7292	Intermediate Similarity	NPD6399	Phase 3
0.7263	Intermediate Similarity	NPD5207	Approved
0.7245	Intermediate Similarity	NPD5222	Approved
0.7245	Intermediate Similarity	NPD4697	Phase 3
0.7245	Intermediate Similarity	NPD5221	Approved
0.7245	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4633	Approved
0.7228	Intermediate Similarity	NPD5224	Approved
0.7228	Intermediate Similarity	NPD5226	Approved
0.7228	Intermediate Similarity	NPD5225	Approved
0.72	Intermediate Similarity	NPD4700	Approved
0.7174	Intermediate Similarity	NPD3668	Phase 3
0.7172	Intermediate Similarity	NPD5173	Approved
0.7157	Intermediate Similarity	NPD5174	Approved
0.7157	Intermediate Similarity	NPD5175	Approved
0.7156	Intermediate Similarity	NPD7115	Discovery
0.7111	Intermediate Similarity	NPD4748	Discontinued
0.71	Intermediate Similarity	NPD5696	Approved
0.7083	Intermediate Similarity	NPD5692	Phase 3
0.7075	Intermediate Similarity	NPD4634	Approved
0.7059	Intermediate Similarity	NPD4747	Approved
0.7059	Intermediate Similarity	NPD5091	Approved
0.7059	Intermediate Similarity	NPD4691	Approved
0.7053	Intermediate Similarity	NPD5208	Approved
0.7041	Intermediate Similarity	NPD6001	Approved
0.7024	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5360	Phase 3
0.7021	Intermediate Similarity	NPD6098	Approved
0.7011	Intermediate Similarity	NPD5733	Approved
0.7011	Intermediate Similarity	NPD4785	Approved
0.7011	Intermediate Similarity	NPD4784	Approved
0.7011	Intermediate Similarity	NPD4687	Approved
0.701	Intermediate Similarity	NPD5693	Phase 1
0.701	Intermediate Similarity	NPD6050	Approved
0.701	Intermediate Similarity	NPD5694	Approved
0.7	Intermediate Similarity	NPD6083	Phase 2
0.7	Intermediate Similarity	NPD6084	Phase 2
0.699	Remote Similarity	NPD4754	Approved
0.6979	Remote Similarity	NPD6904	Approved
0.6979	Remote Similarity	NPD6080	Approved
0.6979	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6673	Approved
0.6977	Remote Similarity	NPD5276	Approved
0.6977	Remote Similarity	NPD4243	Approved
0.697	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5697	Approved
0.6947	Remote Similarity	NPD3573	Approved
0.6941	Remote Similarity	NPD4137	Phase 3
0.6915	Remote Similarity	NPD1696	Phase 3
0.6887	Remote Similarity	NPD5128	Approved
0.6887	Remote Similarity	NPD6899	Approved
0.6887	Remote Similarity	NPD6011	Approved
0.6887	Remote Similarity	NPD4729	Approved
0.6887	Remote Similarity	NPD4730	Approved
0.6887	Remote Similarity	NPD6881	Approved
0.6863	Remote Similarity	NPD6404	Discontinued
0.6857	Remote Similarity	NPD7128	Approved
0.6857	Remote Similarity	NPD4767	Approved
0.6857	Remote Similarity	NPD4768	Approved
0.6857	Remote Similarity	NPD6402	Approved
0.6857	Remote Similarity	NPD6675	Approved
0.6857	Remote Similarity	NPD5739	Approved
0.6854	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6649	Approved
0.6852	Remote Similarity	NPD6650	Approved
0.6842	Remote Similarity	NPD7334	Approved
0.6842	Remote Similarity	NPD5330	Approved
0.6842	Remote Similarity	NPD6684	Approved
0.6842	Remote Similarity	NPD7146	Approved
0.6842	Remote Similarity	NPD7521	Approved
0.6842	Remote Similarity	NPD6409	Approved
0.6837	Remote Similarity	NPD7515	Phase 2
0.6822	Remote Similarity	NPD6373	Approved
0.6822	Remote Similarity	NPD6012	Approved
0.6822	Remote Similarity	NPD6013	Approved
0.6822	Remote Similarity	NPD6014	Approved
0.6822	Remote Similarity	NPD6372	Approved
0.6818	Remote Similarity	NPD4058	Approved
0.68	Remote Similarity	NPD5654	Approved
0.6792	Remote Similarity	NPD5701	Approved
0.6782	Remote Similarity	NPD4758	Discontinued
0.6771	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5135	Approved
0.6759	Remote Similarity	NPD6883	Approved
0.6759	Remote Similarity	NPD5251	Approved
0.6759	Remote Similarity	NPD5249	Phase 3
0.6759	Remote Similarity	NPD5169	Approved
0.6759	Remote Similarity	NPD5248	Approved
0.6759	Remote Similarity	NPD5247	Approved
0.6759	Remote Similarity	NPD7290	Approved
0.6759	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5250	Approved
0.6759	Remote Similarity	NPD7102	Approved
0.6742	Remote Similarity	NPD4190	Phase 3
0.6742	Remote Similarity	NPD6942	Approved
0.6742	Remote Similarity	NPD7339	Approved
0.6742	Remote Similarity	NPD5275	Approved
0.6737	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7320	Approved
0.6701	Remote Similarity	NPD6903	Approved
0.6701	Remote Similarity	NPD5737	Approved
0.6701	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6672	Approved
0.67	Remote Similarity	NPD7748	Approved
0.6698	Remote Similarity	NPD6008	Approved
0.6697	Remote Similarity	NPD6847	Approved
0.6697	Remote Similarity	NPD5217	Approved
0.6697	Remote Similarity	NPD6617	Approved
0.6697	Remote Similarity	NPD5216	Approved
0.6697	Remote Similarity	NPD6869	Approved
0.6697	Remote Similarity	NPD8130	Phase 1
0.6697	Remote Similarity	NPD5215	Approved
0.6697	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD7341	Phase 2
0.6667	Remote Similarity	NPD5959	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6636	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD8297	Approved
0.6628	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4225	Approved
0.6591	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4224	Phase 2
0.6577	Remote Similarity	NPD4632	Approved
0.6574	Remote Similarity	NPD5168	Approved
0.6569	Remote Similarity	NPD7614	Phase 1
0.6566	Remote Similarity	NPD5785	Approved
0.6562	Remote Similarity	NPD5363	Approved
0.6562	Remote Similarity	NPD1694	Approved
0.6559	Remote Similarity	NPD7525	Registered
0.6552	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7639	Approved
0.6538	Remote Similarity	NPD7640	Approved
0.6522	Remote Similarity	NPD6054	Approved
0.6522	Remote Similarity	NPD6319	Approved
0.6518	Remote Similarity	NPD5167	Approved
0.65	Remote Similarity	NPD6411	Approved
0.65	Remote Similarity	NPD8035	Phase 2
0.65	Remote Similarity	NPD8034	Phase 2
0.6471	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6015	Approved
0.6466	Remote Similarity	NPD6016	Approved
0.646	Remote Similarity	NPD6274	Approved
0.6442	Remote Similarity	NPD7638	Approved
0.6421	Remote Similarity	NPD4270	Approved
0.6421	Remote Similarity	NPD4269	Approved
0.6421	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5988	Approved
0.641	Remote Similarity	NPD6370	Approved
0.6404	Remote Similarity	NPD6009	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