NPASS Compound

Structure

NPC110780 OpenBabel07101718312D 22 25 0 0 1 0 0 0 0 0999 V2000 -1.4576 -2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8709 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3709 -0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2424 -1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 -2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2650 -1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5630 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8709 -1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -1.8002 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 -0.0896 -0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0646 -1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5775 -0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.7201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2472 -0.7201 0.0000 C 0 0 1 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 -0.9195 0.3930 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8709 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -1.0801 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 0.6236 1.3600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1420 1.3680 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 7 14 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 6 1 1 0 0 0 13 17 1 0 0 0 0 14 19 1 1 0 0 0 14 20 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 1 0 0 0 16 20 1 0 0 0 0 16 21 2 0 0 0 0 17 20 1 6 0 0 0 17 22 1 0 0 0 0 19 4 1 1 0 0 0 20 11 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	332.558
LogP:	4.108
LogD:	3.999
LogS:	-4.405
# 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:	0.683
Synthetic Accessibility Score:	5.787
Fsp3:	0.85
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:	-4.874
MDCK Permeability:	1.644680742174387e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.051
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.878
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.75
Plasma Protein Binding (PPB):	78.27769470214844%
Volume Distribution (VD):	0.802
Pgp-substrate:	22.117414474487305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.439
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.084
CYP2C9-substrate:	0.213
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.521
CYP3A4-inhibitor:	0.28
CYP3A4-substrate:	0.276

ADMET: Excretion

Clearance (CL):	14.556
Half-life (T1/2):	0.236

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.602
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.88
Maximum Recommended Daily Dose:	0.52
Skin Sensitization:	0.118
Carcinogencity:	0.443
Eye Corrosion:	0.366
Eye Irritation:	0.212
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC110780

Natural Product ID:	NPC110780
*Common Name:**	Crotonkinin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FKUNRSJLNKRKMY-QAINLGQKSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-12-11-20-14(7-6-13(12)17(20)22)19(4)9-5-8-18(2,3)15(19)10-16(20)21/h13-15,17,22H,1,5-11H2,2-4H3/t13-,14-,15+,17+,19-,20-/m1/s1
SMILES:	C=C1C[C@@]23[C@H](CC[C@H]1[C@@H]3O)[C@@]1(C)CCCC(C)(C)[C@@H]1CC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399742
PubChem CID:	24763478
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510600]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18161942]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[19899773]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22085418]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22085418]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22197145]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	whole plants	Vietnam	2009-Aug	PMID[23347584]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	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	1
Others	7

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	Inhibition	<	50.0	%	PMID[480237]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	<	50.0	%	PMID[480237]
NPT91	Cell Line	KB	Homo sapiens	Inhibition	<	50.0	%	PMID[480237]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	<	50.0	%	PMID[480237]
NPT2	Others	Unspecified		Inhibition	=	11.2	%	PMID[480237]
NPT2	Others	Unspecified		IC50	=	46200.0	nM	PMID[480237]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-9.32	%	PMID[480238]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	1.65	%	PMID[480238]

☑ 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 NPC110780 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	173
0.1-0.2	1600
0.2-0.3	6651
0.3-0.4	15583
0.4-0.5	6773
0.5-0.6	5566
0.6-0.7	4293
0.7-0.8	1752
0.8-0.85	219
0.85-0.9	72
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.962	High Similarity	NPC102292
0.9383	High Similarity	NPC165895
0.9367	High Similarity	NPC471036
0.9367	High Similarity	NPC291320
0.9241	High Similarity	NPC46881
0.9136	High Similarity	NPC471034
0.9136	High Similarity	NPC190704
0.9048	High Similarity	NPC261994
0.9048	High Similarity	NPC180849
0.9048	High Similarity	NPC470378
0.9048	High Similarity	NPC149761
0.8941	High Similarity	NPC278106
0.8941	High Similarity	NPC476168
0.8941	High Similarity	NPC299185
0.8916	High Similarity	NPC259009
0.8916	High Similarity	NPC57469
0.8889	High Similarity	NPC472743
0.8889	High Similarity	NPC118800
0.8889	High Similarity	NPC475726
0.8846	High Similarity	NPC106078
0.8837	High Similarity	NPC82138
0.8837	High Similarity	NPC59170
0.8837	High Similarity	NPC181594
0.8837	High Similarity	NPC144739
0.8837	High Similarity	NPC59350
0.8824	High Similarity	NPC80401
0.878	High Similarity	NPC474482
0.878	High Similarity	NPC146683
0.878	High Similarity	NPC475745
0.8736	High Similarity	NPC261333
0.8736	High Similarity	NPC111524
0.8736	High Similarity	NPC215271
0.8736	High Similarity	NPC129004
0.8736	High Similarity	NPC91772
0.8736	High Similarity	NPC302008
0.8736	High Similarity	NPC64006
0.8736	High Similarity	NPC292374
0.8736	High Similarity	NPC104371
0.8736	High Similarity	NPC101233
0.8736	High Similarity	NPC191094
0.8736	High Similarity	NPC153775
0.8736	High Similarity	NPC29247
0.8736	High Similarity	NPC289539
0.869	High Similarity	NPC472495
0.869	High Similarity	NPC174619
0.869	High Similarity	NPC472497
0.8675	High Similarity	NPC76518
0.8675	High Similarity	NPC292553
0.8659	High Similarity	NPC245866
0.8659	High Similarity	NPC472498
0.8642	High Similarity	NPC328264
0.8636	High Similarity	NPC138245
0.8636	High Similarity	NPC84018
0.8636	High Similarity	NPC210214
0.8636	High Similarity	NPC29112
0.8636	High Similarity	NPC231060
0.8625	High Similarity	NPC201459
0.8588	High Similarity	NPC146937
0.8588	High Similarity	NPC328313
0.8588	High Similarity	NPC471900
0.8571	High Similarity	NPC472738
0.8554	High Similarity	NPC474233
0.8554	High Similarity	NPC264665
0.8554	High Similarity	NPC74595
0.8539	High Similarity	NPC13949
0.8539	High Similarity	NPC264979
0.8539	High Similarity	NPC140242
0.8539	High Similarity	NPC135548
0.8537	High Similarity	NPC477858
0.8537	High Similarity	NPC170985
0.8537	High Similarity	NPC145143
0.8519	High Similarity	NPC164999
0.8506	High Similarity	NPC211403
0.8506	High Similarity	NPC250753
0.8506	High Similarity	NPC198242
0.8488	Intermediate Similarity	NPC57954
0.8488	Intermediate Similarity	NPC213832
0.8471	Intermediate Similarity	NPC4643
0.8471	Intermediate Similarity	NPC153604
0.8471	Intermediate Similarity	NPC134197
0.8452	Intermediate Similarity	NPC264317
0.8452	Intermediate Similarity	NPC294438
0.8452	Intermediate Similarity	NPC201655
0.8434	Intermediate Similarity	NPC471037
0.8415	Intermediate Similarity	NPC474484
0.8415	Intermediate Similarity	NPC103754
0.8391	Intermediate Similarity	NPC169933
0.8391	Intermediate Similarity	NPC100313
0.8375	Intermediate Similarity	NPC472746
0.8372	Intermediate Similarity	NPC211162
0.8372	Intermediate Similarity	NPC193360
0.8372	Intermediate Similarity	NPC472739
0.8372	Intermediate Similarity	NPC183374
0.8372	Intermediate Similarity	NPC474719
0.8372	Intermediate Similarity	NPC53911
0.8372	Intermediate Similarity	NPC471724
0.8353	Intermediate Similarity	NPC12774
0.8353	Intermediate Similarity	NPC2783
0.8353	Intermediate Similarity	NPC98236
0.8353	Intermediate Similarity	NPC269396
0.8352	Intermediate Similarity	NPC78427
0.8352	Intermediate Similarity	NPC16911
0.8333	Intermediate Similarity	NPC221758
0.8333	Intermediate Similarity	NPC263974
0.8333	Intermediate Similarity	NPC82902
0.8333	Intermediate Similarity	NPC59453
0.8315	Intermediate Similarity	NPC280804
0.8315	Intermediate Similarity	NPC470386
0.8315	Intermediate Similarity	NPC47853
0.8315	Intermediate Similarity	NPC470385
0.8313	Intermediate Similarity	NPC151519
0.8295	Intermediate Similarity	NPC475416
0.8276	Intermediate Similarity	NPC472971
0.8276	Intermediate Similarity	NPC116146
0.8276	Intermediate Similarity	NPC24772
0.8276	Intermediate Similarity	NPC472970
0.8261	Intermediate Similarity	NPC287676
0.8261	Intermediate Similarity	NPC127408
0.8261	Intermediate Similarity	NPC291785
0.8261	Intermediate Similarity	NPC55503
0.8261	Intermediate Similarity	NPC156324
0.8256	Intermediate Similarity	NPC264005
0.8256	Intermediate Similarity	NPC472481
0.8256	Intermediate Similarity	NPC475740
0.8256	Intermediate Similarity	NPC472482
0.8256	Intermediate Similarity	NPC33768
0.8256	Intermediate Similarity	NPC472484
0.8256	Intermediate Similarity	NPC269360
0.8242	Intermediate Similarity	NPC170978
0.8235	Intermediate Similarity	NPC474218
0.8222	Intermediate Similarity	NPC205173
0.8222	Intermediate Similarity	NPC266431
0.8222	Intermediate Similarity	NPC472485
0.8222	Intermediate Similarity	NPC470232
0.8214	Intermediate Similarity	NPC175410
0.8202	Intermediate Similarity	NPC12722
0.8202	Intermediate Similarity	NPC287118
0.8202	Intermediate Similarity	NPC473690
0.8202	Intermediate Similarity	NPC471902
0.8202	Intermediate Similarity	NPC472496
0.8193	Intermediate Similarity	NPC164210
0.8193	Intermediate Similarity	NPC14151
0.8182	Intermediate Similarity	NPC126993
0.8182	Intermediate Similarity	NPC46758
0.8172	Intermediate Similarity	NPC163963
0.8172	Intermediate Similarity	NPC60947
0.8172	Intermediate Similarity	NPC52899
0.8172	Intermediate Similarity	NPC289148
0.8172	Intermediate Similarity	NPC471790
0.8161	Intermediate Similarity	NPC471722
0.8161	Intermediate Similarity	NPC328539
0.8161	Intermediate Similarity	NPC474677
0.8161	Intermediate Similarity	NPC16377
0.8148	Intermediate Similarity	NPC471035
0.8148	Intermediate Similarity	NPC212661
0.8148	Intermediate Similarity	NPC149249
0.814	Intermediate Similarity	NPC145879
0.814	Intermediate Similarity	NPC472491
0.814	Intermediate Similarity	NPC474732
0.814	Intermediate Similarity	NPC469994
0.814	Intermediate Similarity	NPC474778
0.814	Intermediate Similarity	NPC470955
0.814	Intermediate Similarity	NPC72133
0.814	Intermediate Similarity	NPC51014
0.814	Intermediate Similarity	NPC70661
0.814	Intermediate Similarity	NPC474733
0.814	Intermediate Similarity	NPC31564
0.814	Intermediate Similarity	NPC472494
0.814	Intermediate Similarity	NPC80590
0.8132	Intermediate Similarity	NPC470387
0.8132	Intermediate Similarity	NPC234564
0.8132	Intermediate Similarity	NPC329910
0.8118	Intermediate Similarity	NPC161423
0.8118	Intermediate Similarity	NPC227064
0.8118	Intermediate Similarity	NPC329043
0.8118	Intermediate Similarity	NPC214043
0.8118	Intermediate Similarity	NPC85774
0.8118	Intermediate Similarity	NPC58841
0.8118	Intermediate Similarity	NPC321187
0.8111	Intermediate Similarity	NPC475118
0.8101	Intermediate Similarity	NPC161187
0.8101	Intermediate Similarity	NPC330659
0.8101	Intermediate Similarity	NPC232112
0.8101	Intermediate Similarity	NPC244708
0.809	Intermediate Similarity	NPC272746
0.809	Intermediate Similarity	NPC471901
0.8085	Intermediate Similarity	NPC148628
0.8085	Intermediate Similarity	NPC475803
0.8085	Intermediate Similarity	NPC272472
0.8085	Intermediate Similarity	NPC246736
0.8085	Intermediate Similarity	NPC286519
0.8085	Intermediate Similarity	NPC214946
0.8085	Intermediate Similarity	NPC76866
0.8085	Intermediate Similarity	NPC304832
0.8085	Intermediate Similarity	NPC309388
0.8085	Intermediate Similarity	NPC88203
0.8077	Intermediate Similarity	NPC45296
0.8077	Intermediate Similarity	NPC476731
0.8072	Intermediate Similarity	NPC472478
0.8068	Intermediate Similarity	NPC122116

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 NPC110780 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	2016
0.2-0.3	4252
0.3-0.4	1859
0.4-0.5	440
0.5-0.6	143
0.6-0.7	177
0.7-0.8	87
0.8-0.85	15
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8452	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD4788	Approved
0.8333	Intermediate Similarity	NPD4786	Approved
0.8313	Intermediate Similarity	NPD3667	Approved
0.814	Intermediate Similarity	NPD3618	Phase 1
0.8118	Intermediate Similarity	NPD3133	Approved
0.8118	Intermediate Similarity	NPD3666	Approved
0.8118	Intermediate Similarity	NPD3665	Phase 1
0.8068	Intermediate Similarity	NPD5328	Approved
0.8	Intermediate Similarity	NPD4202	Approved
0.7975	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD3698	Phase 2
0.7889	Intermediate Similarity	NPD6079	Approved
0.7848	Intermediate Similarity	NPD4245	Approved
0.7848	Intermediate Similarity	NPD4244	Approved
0.7727	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8034	Phase 2
0.7692	Intermediate Similarity	NPD8035	Phase 2
0.7683	Intermediate Similarity	NPD3703	Phase 2
0.7674	Intermediate Similarity	NPD4223	Phase 3
0.7674	Intermediate Similarity	NPD4221	Approved
0.7667	Intermediate Similarity	NPD4753	Phase 2
0.7662	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD4755	Approved
0.7625	Intermediate Similarity	NPD4789	Approved
0.759	Intermediate Similarity	NPD6117	Approved
0.7561	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD5222	Approved
0.7553	Intermediate Similarity	NPD4697	Phase 3
0.7553	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD5221	Approved
0.7528	Intermediate Similarity	NPD5279	Phase 3
0.75	Intermediate Similarity	NPD4197	Approved
0.75	Intermediate Similarity	NPD5286	Approved
0.75	Intermediate Similarity	NPD3668	Phase 3
0.75	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD4700	Approved
0.75	Intermediate Similarity	NPD6116	Phase 1
0.75	Intermediate Similarity	NPD4696	Approved
0.75	Intermediate Similarity	NPD5285	Approved
0.7474	Intermediate Similarity	NPD5173	Approved
0.7442	Intermediate Similarity	NPD7525	Registered
0.7423	Intermediate Similarity	NPD5223	Approved
0.7419	Intermediate Similarity	NPD6399	Phase 3
0.7416	Intermediate Similarity	NPD5329	Approved
0.7412	Intermediate Similarity	NPD6114	Approved
0.7412	Intermediate Similarity	NPD6697	Approved
0.7412	Intermediate Similarity	NPD6115	Approved
0.7412	Intermediate Similarity	NPD6118	Approved
0.7381	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5360	Phase 3
0.7347	Intermediate Similarity	NPD4633	Approved
0.7347	Intermediate Similarity	NPD5226	Approved
0.7347	Intermediate Similarity	NPD5224	Approved
0.7347	Intermediate Similarity	NPD5211	Phase 2
0.7347	Intermediate Similarity	NPD5225	Approved
0.7342	Intermediate Similarity	NPD4224	Phase 2
0.7333	Intermediate Similarity	NPD4693	Phase 3
0.7333	Intermediate Similarity	NPD4138	Approved
0.7333	Intermediate Similarity	NPD5205	Approved
0.7333	Intermediate Similarity	NPD4690	Approved
0.7333	Intermediate Similarity	NPD4688	Approved
0.7333	Intermediate Similarity	NPD4689	Approved
0.7273	Intermediate Similarity	NPD5175	Approved
0.7273	Intermediate Similarity	NPD5174	Approved
0.7273	Intermediate Similarity	NPD4754	Approved
0.7263	Intermediate Similarity	NPD5210	Approved
0.7263	Intermediate Similarity	NPD4629	Approved
0.7262	Intermediate Similarity	NPD7339	Approved
0.7262	Intermediate Similarity	NPD6942	Approved
0.7209	Intermediate Similarity	NPD3617	Approved
0.7209	Intermediate Similarity	NPD3671	Phase 1
0.72	Intermediate Similarity	NPD5141	Approved
0.7184	Intermediate Similarity	NPD4634	Approved
0.7174	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4692	Approved
0.7159	Intermediate Similarity	NPD4139	Approved
0.7158	Intermediate Similarity	NPD7748	Approved
0.7143	Intermediate Similarity	NPD5280	Approved
0.7143	Intermediate Similarity	NPD7521	Approved
0.7143	Intermediate Similarity	NPD7334	Approved
0.7143	Intermediate Similarity	NPD6684	Approved
0.7143	Intermediate Similarity	NPD7146	Approved
0.7143	Intermediate Similarity	NPD6409	Approved
0.7143	Intermediate Similarity	NPD5330	Approved
0.7143	Intermediate Similarity	NPD4694	Approved
0.7143	Intermediate Similarity	NPD5690	Phase 2
0.7129	Intermediate Similarity	NPD4767	Approved
0.7129	Intermediate Similarity	NPD5739	Approved
0.7129	Intermediate Similarity	NPD4768	Approved
0.7129	Intermediate Similarity	NPD6402	Approved
0.7129	Intermediate Similarity	NPD6675	Approved
0.7129	Intermediate Similarity	NPD7128	Approved
0.7113	Intermediate Similarity	NPD6083	Phase 2
0.7113	Intermediate Similarity	NPD6084	Phase 2
0.7108	Intermediate Similarity	NPD4758	Discontinued
0.7059	Intermediate Similarity	NPD5701	Approved
0.7059	Intermediate Similarity	NPD5697	Approved
0.7045	Intermediate Similarity	NPD4695	Discontinued
0.699	Remote Similarity	NPD4729	Approved
0.699	Remote Similarity	NPD6881	Approved
0.699	Remote Similarity	NPD7320	Approved
0.699	Remote Similarity	NPD6011	Approved
0.699	Remote Similarity	NPD5128	Approved
0.699	Remote Similarity	NPD4730	Approved
0.699	Remote Similarity	NPD6899	Approved
0.6989	Remote Similarity	NPD6903	Approved
0.6941	Remote Similarity	NPD6926	Approved
0.6941	Remote Similarity	NPD6924	Approved
0.6939	Remote Similarity	NPD7902	Approved
0.6932	Remote Similarity	NPD7645	Phase 2
0.6932	Remote Similarity	NPD4195	Approved
0.6923	Remote Similarity	NPD6014	Approved
0.6923	Remote Similarity	NPD6372	Approved
0.6923	Remote Similarity	NPD6012	Approved
0.6923	Remote Similarity	NPD6013	Approved
0.6923	Remote Similarity	NPD6373	Approved
0.6907	Remote Similarity	NPD5695	Phase 3
0.6905	Remote Similarity	NPD6081	Approved
0.6905	Remote Similarity	NPD5777	Approved
0.6869	Remote Similarity	NPD5696	Approved
0.6869	Remote Similarity	NPD7638	Approved
0.686	Remote Similarity	NPD3702	Approved
0.6857	Remote Similarity	NPD5247	Approved
0.6857	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5135	Approved
0.6857	Remote Similarity	NPD5251	Approved
0.6857	Remote Similarity	NPD5248	Approved
0.6857	Remote Similarity	NPD5169	Approved
0.6857	Remote Similarity	NPD6883	Approved
0.6857	Remote Similarity	NPD5249	Phase 3
0.6857	Remote Similarity	NPD5250	Approved
0.6857	Remote Similarity	NPD7290	Approved
0.6857	Remote Similarity	NPD7102	Approved
0.6854	Remote Similarity	NPD4748	Discontinued
0.6827	Remote Similarity	NPD5168	Approved
0.6809	Remote Similarity	NPD6672	Approved
0.6809	Remote Similarity	NPD5737	Approved
0.68	Remote Similarity	NPD7640	Approved
0.68	Remote Similarity	NPD7639	Approved
0.6792	Remote Similarity	NPD5127	Approved
0.6792	Remote Similarity	NPD6847	Approved
0.6792	Remote Similarity	NPD6617	Approved
0.6792	Remote Similarity	NPD6650	Approved
0.6792	Remote Similarity	NPD8130	Phase 1
0.6792	Remote Similarity	NPD6869	Approved
0.6792	Remote Similarity	NPD5215	Approved
0.6792	Remote Similarity	NPD5217	Approved
0.6792	Remote Similarity	NPD6649	Approved
0.6792	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5216	Approved
0.6789	Remote Similarity	NPD7115	Discovery
0.6786	Remote Similarity	NPD4747	Approved
0.6782	Remote Similarity	NPD6933	Approved
0.6774	Remote Similarity	NPD6098	Approved
0.6774	Remote Similarity	NPD4623	Approved
0.6774	Remote Similarity	NPD4519	Discontinued
0.6771	Remote Similarity	NPD6411	Approved
0.6771	Remote Similarity	NPD5281	Approved
0.6771	Remote Similarity	NPD5284	Approved
0.6744	Remote Similarity	NPD4784	Approved
0.6744	Remote Similarity	NPD4785	Approved
0.6735	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD8297	Approved
0.6729	Remote Similarity	NPD6882	Approved
0.6706	Remote Similarity	NPD4243	Approved
0.6702	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6923	Approved
0.6667	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4137	Phase 3
0.6667	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD4096	Approved
0.6667	Remote Similarity	NPD6922	Approved
0.6635	Remote Similarity	NPD6008	Approved
0.6633	Remote Similarity	NPD6001	Approved
0.6633	Remote Similarity	NPD7900	Approved
0.6633	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4518	Approved
0.6632	Remote Similarity	NPD5208	Approved
0.6629	Remote Similarity	NPD5364	Discontinued
0.6607	Remote Similarity	NPD6059	Approved
0.6607	Remote Similarity	NPD6319	Approved
0.6607	Remote Similarity	NPD6054	Approved
0.6606	Remote Similarity	NPD5167	Approved
0.6593	Remote Similarity	NPD5369	Approved
0.6588	Remote Similarity	NPD4691	Approved
0.6588	Remote Similarity	NPD7143	Approved
0.6588	Remote Similarity	NPD7144	Approved
0.6588	Remote Similarity	NPD4787	Phase 1
0.6571	Remote Similarity	NPD6412	Phase 2
0.6562	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6080	Approved
0.6562	Remote Similarity	NPD6904	Approved
0.6562	Remote Similarity	NPD6101	Approved
0.6562	Remote Similarity	NPD6673	Approved
0.6562	Remote Similarity	NPD5764	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