NPASS Compound

Structure

NPC471036 OpenBabel07101719242D 22 25 0 0 1 0 0 0 0 0999 V2000 2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3997 -1.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3998 -1.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 1.0185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 0.0373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2172 1.6034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7148 1.0829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5050 -0.6827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8653 0.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6397 -1.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6182 0.3693 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2579 -0.7014 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0108 -0.7200 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8868 -1.0520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2471 0.0187 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 0.8477 -1.2329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 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 13 1 0 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 6 1 6 0 0 0 14 19 1 6 0 0 0 14 20 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 6 0 0 0 16 20 1 1 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 17 22 2 0 0 0 0 19 4 1 6 0 0 0 20 11 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	332.558
LogP:	3.816
LogD:	3.996
LogS:	-4.287
# 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:	5.623
Fsp3:	0.85
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:	-4.772
MDCK Permeability:	2.2609252482652664e-05
Pgp-inhibitor:	0.035
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.949
30% Bioavailability (F30%):	0.844

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.508
Plasma Protein Binding (PPB):	82.4438247680664%
Volume Distribution (VD):	0.782
Pgp-substrate:	21.627382278442383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.083
CYP1A2-substrate:	0.309
CYP2C19-inhibitor:	0.131
CYP2C19-substrate:	0.761
CYP2C9-inhibitor:	0.44
CYP2C9-substrate:	0.391
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.675
CYP3A4-inhibitor:	0.306
CYP3A4-substrate:	0.228

ADMET: Excretion

Clearance (CL):	7.259
Half-life (T1/2):	0.125

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.095
Drug-inuced Liver Injury (DILI):	0.085
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.982
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.944
Carcinogencity:	0.398
Eye Corrosion:	0.873
Eye Irritation:	0.872
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC471036

Natural Product ID:	NPC471036
*Common Name:**	IFUJUCUWCLVMER-VNXBCOTQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IFUJUCUWCLVMER-VNXBCOTQSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-12-13-6-7-14-19(4)9-5-8-18(2,3)15(19)10-16(21)20(14,11-13)17(12)22/h13-16,21H,1,5-11H2,2-4H3/t13-,14-,15+,16-,19-,20+/m0/s1
SMILES:	CC1(CCCC2(C1CC(C34C2CCC(C3)C(=C)C4=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337573
PubChem CID:	71717074
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	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2230.0	nM	PMID[570596]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1740.0	nM	PMID[570596]

☑ 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 NPC471036 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	176
0.1-0.2	1591
0.2-0.3	6595
0.3-0.4	15226
0.4-0.5	6948
0.5-0.6	5524
0.6-0.7	4442
0.7-0.8	1846
0.8-0.85	239
0.85-0.9	80
0.9-0.95	23
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC291320
0.9747	High Similarity	NPC471034
0.9747	High Similarity	NPC190704
0.9506	High Similarity	NPC259009
0.9506	High Similarity	NPC165895
0.95	High Similarity	NPC102292
0.9375	High Similarity	NPC146683
0.9367	High Similarity	NPC110780
0.9259	High Similarity	NPC76518
0.925	High Similarity	NPC118800
0.9221	High Similarity	NPC106078
0.9167	High Similarity	NPC261994
0.9167	High Similarity	NPC470378
0.9167	High Similarity	NPC149761
0.9167	High Similarity	NPC180849
0.9167	High Similarity	NPC80401
0.9059	High Similarity	NPC198242
0.9059	High Similarity	NPC211403
0.9059	High Similarity	NPC299185
0.9059	High Similarity	NPC476168
0.9036	High Similarity	NPC57469
0.9036	High Similarity	NPC174619
0.9036	High Similarity	NPC153604
0.9012	High Similarity	NPC472743
0.9012	High Similarity	NPC475726
0.8953	High Similarity	NPC59170
0.8953	High Similarity	NPC144739
0.8953	High Similarity	NPC59350
0.8953	High Similarity	NPC181594
0.8929	High Similarity	NPC472739
0.8929	High Similarity	NPC471724
0.8916	High Similarity	NPC269396
0.8916	High Similarity	NPC98236
0.8902	High Similarity	NPC475745
0.8902	High Similarity	NPC474482
0.8889	High Similarity	NPC46881
0.8851	High Similarity	NPC91772
0.8851	High Similarity	NPC470386
0.8851	High Similarity	NPC29247
0.8851	High Similarity	NPC261333
0.8851	High Similarity	NPC47853
0.8851	High Similarity	NPC111524
0.8851	High Similarity	NPC101233
0.8851	High Similarity	NPC153775
0.8851	High Similarity	NPC191094
0.8851	High Similarity	NPC129004
0.8851	High Similarity	NPC289539
0.8851	High Similarity	NPC104371
0.8851	High Similarity	NPC215271
0.8851	High Similarity	NPC64006
0.8851	High Similarity	NPC470385
0.8851	High Similarity	NPC302008
0.8851	High Similarity	NPC292374
0.8837	High Similarity	NPC250753
0.8837	High Similarity	NPC278106
0.8795	High Similarity	NPC292553
0.875	High Similarity	NPC470232
0.875	High Similarity	NPC231060
0.875	High Similarity	NPC210214
0.875	High Similarity	NPC29112
0.875	High Similarity	NPC138245
0.875	High Similarity	NPC84018
0.8736	High Similarity	NPC82138
0.8721	High Similarity	NPC126993
0.8706	High Similarity	NPC471900
0.8706	High Similarity	NPC146937
0.869	High Similarity	NPC472738
0.8675	High Similarity	NPC264665
0.8675	High Similarity	NPC474233
0.8675	High Similarity	NPC74595
0.8652	High Similarity	NPC264979
0.8652	High Similarity	NPC470387
0.8652	High Similarity	NPC135548
0.8652	High Similarity	NPC13949
0.8652	High Similarity	NPC140242
0.8652	High Similarity	NPC329910
0.8642	High Similarity	NPC164999
0.8636	High Similarity	NPC475118
0.8621	High Similarity	NPC272746
0.8605	High Similarity	NPC57954
0.8605	High Similarity	NPC213832
0.8588	High Similarity	NPC472495
0.8588	High Similarity	NPC4643
0.8588	High Similarity	NPC472497
0.8571	High Similarity	NPC264317
0.8571	High Similarity	NPC294438
0.8554	High Similarity	NPC175410
0.8539	High Similarity	NPC470229
0.8537	High Similarity	NPC328264
0.8523	High Similarity	NPC294263
0.8519	High Similarity	NPC201459
0.8506	High Similarity	NPC85173
0.8506	High Similarity	NPC169933
0.85	High Similarity	NPC149249
0.85	High Similarity	NPC212661
0.85	High Similarity	NPC472746
0.85	High Similarity	NPC471035
0.8488	Intermediate Similarity	NPC474677
0.8488	Intermediate Similarity	NPC474719
0.8488	Intermediate Similarity	NPC193360
0.8488	Intermediate Similarity	NPC328539
0.8471	Intermediate Similarity	NPC2783
0.8471	Intermediate Similarity	NPC72133
0.8471	Intermediate Similarity	NPC12774
0.8471	Intermediate Similarity	NPC34190
0.8462	Intermediate Similarity	NPC16911
0.8462	Intermediate Similarity	NPC78427
0.8462	Intermediate Similarity	NPC471038
0.8462	Intermediate Similarity	NPC288
0.8462	Intermediate Similarity	NPC109059
0.8434	Intermediate Similarity	NPC477858
0.8434	Intermediate Similarity	NPC145143
0.8415	Intermediate Similarity	NPC472478
0.8409	Intermediate Similarity	NPC475416
0.8391	Intermediate Similarity	NPC119416
0.8391	Intermediate Similarity	NPC471043
0.8372	Intermediate Similarity	NPC264005
0.8372	Intermediate Similarity	NPC269360
0.8372	Intermediate Similarity	NPC33768
0.8372	Intermediate Similarity	NPC475740
0.837	Intermediate Similarity	NPC470388
0.837	Intermediate Similarity	NPC287676
0.837	Intermediate Similarity	NPC127408
0.837	Intermediate Similarity	NPC291785
0.837	Intermediate Similarity	NPC55503
0.837	Intermediate Similarity	NPC156324
0.8353	Intermediate Similarity	NPC470574
0.8353	Intermediate Similarity	NPC201655
0.8333	Intermediate Similarity	NPC471037
0.8333	Intermediate Similarity	NPC266431
0.8333	Intermediate Similarity	NPC98639
0.8333	Intermediate Similarity	NPC472498
0.8315	Intermediate Similarity	NPC12722
0.8315	Intermediate Similarity	NPC471902
0.8315	Intermediate Similarity	NPC473690
0.8315	Intermediate Similarity	NPC287118
0.8313	Intermediate Similarity	NPC474484
0.8313	Intermediate Similarity	NPC164210
0.8313	Intermediate Similarity	NPC103754
0.8295	Intermediate Similarity	NPC46758
0.8295	Intermediate Similarity	NPC191684
0.8295	Intermediate Similarity	NPC100313
0.8293	Intermediate Similarity	NPC472490
0.8293	Intermediate Similarity	NPC476812
0.828	Intermediate Similarity	NPC471790
0.828	Intermediate Similarity	NPC163963
0.828	Intermediate Similarity	NPC71706
0.828	Intermediate Similarity	NPC289148
0.828	Intermediate Similarity	NPC52899
0.828	Intermediate Similarity	NPC60947
0.828	Intermediate Similarity	NPC46848
0.8276	Intermediate Similarity	NPC131470
0.8276	Intermediate Similarity	NPC16377
0.8276	Intermediate Similarity	NPC53911
0.8276	Intermediate Similarity	NPC143767
0.8276	Intermediate Similarity	NPC328313
0.8276	Intermediate Similarity	NPC56413
0.8276	Intermediate Similarity	NPC471722
0.8272	Intermediate Similarity	NPC476811
0.8261	Intermediate Similarity	NPC474793
0.8256	Intermediate Similarity	NPC31564
0.8256	Intermediate Similarity	NPC145879
0.8256	Intermediate Similarity	NPC158393
0.8256	Intermediate Similarity	NPC474733
0.8256	Intermediate Similarity	NPC474732
0.8256	Intermediate Similarity	NPC474778
0.8242	Intermediate Similarity	NPC104568
0.8242	Intermediate Similarity	NPC200054
0.8242	Intermediate Similarity	NPC29410
0.8235	Intermediate Similarity	NPC214043
0.8235	Intermediate Similarity	NPC59453
0.8235	Intermediate Similarity	NPC221758
0.8235	Intermediate Similarity	NPC85774
0.8228	Intermediate Similarity	NPC232112
0.8214	Intermediate Similarity	NPC170985
0.8214	Intermediate Similarity	NPC151519
0.8205	Intermediate Similarity	NPC45296
0.8202	Intermediate Similarity	NPC168027
0.8202	Intermediate Similarity	NPC185936
0.8202	Intermediate Similarity	NPC471901
0.8202	Intermediate Similarity	NPC470230
0.8191	Intermediate Similarity	NPC304832
0.8191	Intermediate Similarity	NPC88203
0.8191	Intermediate Similarity	NPC148628
0.8191	Intermediate Similarity	NPC272472
0.8191	Intermediate Similarity	NPC309388
0.8191	Intermediate Similarity	NPC246736
0.8191	Intermediate Similarity	NPC286519
0.8191	Intermediate Similarity	NPC275990
0.8191	Intermediate Similarity	NPC475803
0.8191	Intermediate Similarity	NPC214946
0.8191	Intermediate Similarity	NPC76866
0.8182	Intermediate Similarity	NPC309603
0.8182	Intermediate Similarity	NPC472971
0.8182	Intermediate Similarity	NPC86319
0.8182	Intermediate Similarity	NPC472477
0.8182	Intermediate Similarity	NPC472489
0.8182	Intermediate Similarity	NPC472970
0.8182	Intermediate Similarity	NPC473999
0.8182	Intermediate Similarity	NPC69627

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 NPC471036 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	2047
0.2-0.3	4250
0.3-0.4	1847
0.4-0.5	423
0.5-0.6	147
0.6-0.7	138
0.7-0.8	123
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD7520	Clinical (unspecified phase)
0.8554	High Similarity	NPD4788	Approved
0.8471	Intermediate Similarity	NPD3618	Phase 1
0.8409	Intermediate Similarity	NPD6079	Approved
0.8391	Intermediate Similarity	NPD5328	Approved
0.8235	Intermediate Similarity	NPD4786	Approved
0.8214	Intermediate Similarity	NPD3667	Approved
0.8111	Intermediate Similarity	NPD4202	Approved
0.8101	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD5222	Approved
0.8043	Intermediate Similarity	NPD5221	Approved
0.8043	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD3133	Approved
0.8023	Intermediate Similarity	NPD3666	Approved
0.8023	Intermediate Similarity	NPD3665	Phase 1
0.7957	Intermediate Similarity	NPD5173	Approved
0.7849	Intermediate Similarity	NPD4697	Phase 3
0.7841	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD3703	Phase 2
0.7802	Intermediate Similarity	NPD7515	Phase 2
0.7802	Intermediate Similarity	NPD8034	Phase 2
0.7802	Intermediate Similarity	NPD8035	Phase 2
0.7789	Intermediate Similarity	NPD4696	Approved
0.7789	Intermediate Similarity	NPD5285	Approved
0.7789	Intermediate Similarity	NPD5286	Approved
0.7766	Intermediate Similarity	NPD4755	Approved
0.7711	Intermediate Similarity	NPD6117	Approved
0.7708	Intermediate Similarity	NPD5223	Approved
0.7683	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5279	Phase 3
0.7629	Intermediate Similarity	NPD5224	Approved
0.7629	Intermediate Similarity	NPD4633	Approved
0.7629	Intermediate Similarity	NPD5226	Approved
0.7629	Intermediate Similarity	NPD5225	Approved
0.7629	Intermediate Similarity	NPD5211	Phase 2
0.7625	Intermediate Similarity	NPD3698	Phase 2
0.7619	Intermediate Similarity	NPD6116	Phase 1
0.7604	Intermediate Similarity	NPD4700	Approved
0.7586	Intermediate Similarity	NPD4223	Phase 3
0.7586	Intermediate Similarity	NPD4221	Approved
0.7582	Intermediate Similarity	NPD4753	Phase 2
0.7564	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7525	Registered
0.7551	Intermediate Similarity	NPD5175	Approved
0.7551	Intermediate Similarity	NPD5174	Approved
0.7531	Intermediate Similarity	NPD4789	Approved
0.7531	Intermediate Similarity	NPD4244	Approved
0.7531	Intermediate Similarity	NPD4245	Approved
0.7529	Intermediate Similarity	NPD6115	Approved
0.7529	Intermediate Similarity	NPD6697	Approved
0.7529	Intermediate Similarity	NPD6118	Approved
0.7529	Intermediate Similarity	NPD6114	Approved
0.75	Intermediate Similarity	NPD5360	Phase 3
0.75	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD5141	Approved
0.7451	Intermediate Similarity	NPD4634	Approved
0.7447	Intermediate Similarity	NPD7748	Approved
0.7416	Intermediate Similarity	NPD3668	Phase 3
0.7416	Intermediate Similarity	NPD4197	Approved
0.7374	Intermediate Similarity	NPD4754	Approved
0.7368	Intermediate Similarity	NPD4629	Approved
0.7368	Intermediate Similarity	NPD5210	Approved
0.734	Intermediate Similarity	NPD6399	Phase 3
0.7333	Intermediate Similarity	NPD5329	Approved
0.7327	Intermediate Similarity	NPD5697	Approved
0.7326	Intermediate Similarity	NPD3617	Approved
0.7326	Intermediate Similarity	NPD3671	Phase 1
0.7255	Intermediate Similarity	NPD5128	Approved
0.7255	Intermediate Similarity	NPD6899	Approved
0.7255	Intermediate Similarity	NPD6881	Approved
0.7255	Intermediate Similarity	NPD5168	Approved
0.7255	Intermediate Similarity	NPD6011	Approved
0.7255	Intermediate Similarity	NPD4730	Approved
0.7255	Intermediate Similarity	NPD4729	Approved
0.7253	Intermediate Similarity	NPD4138	Approved
0.7253	Intermediate Similarity	NPD4688	Approved
0.7253	Intermediate Similarity	NPD4693	Phase 3
0.7253	Intermediate Similarity	NPD5690	Phase 2
0.7253	Intermediate Similarity	NPD4689	Approved
0.7253	Intermediate Similarity	NPD5205	Approved
0.7253	Intermediate Similarity	NPD4690	Approved
0.725	Intermediate Similarity	NPD4224	Phase 2
0.7229	Intermediate Similarity	NPD4758	Discontinued
0.7228	Intermediate Similarity	NPD6402	Approved
0.7228	Intermediate Similarity	NPD7128	Approved
0.7228	Intermediate Similarity	NPD5739	Approved
0.7228	Intermediate Similarity	NPD4768	Approved
0.7228	Intermediate Similarity	NPD4767	Approved
0.7228	Intermediate Similarity	NPD6675	Approved
0.7216	Intermediate Similarity	NPD7902	Approved
0.7184	Intermediate Similarity	NPD6014	Approved
0.7184	Intermediate Similarity	NPD6013	Approved
0.7184	Intermediate Similarity	NPD6012	Approved
0.7176	Intermediate Similarity	NPD6942	Approved
0.7176	Intermediate Similarity	NPD7339	Approved
0.7159	Intermediate Similarity	NPD4695	Discontinued
0.7157	Intermediate Similarity	NPD5701	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.7115	Intermediate Similarity	NPD7290	Approved
0.7115	Intermediate Similarity	NPD5247	Approved
0.7115	Intermediate Similarity	NPD5248	Approved
0.7115	Intermediate Similarity	NPD5249	Phase 3
0.7115	Intermediate Similarity	NPD5250	Approved
0.7115	Intermediate Similarity	NPD5251	Approved
0.7115	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6883	Approved
0.7115	Intermediate Similarity	NPD7102	Approved
0.7115	Intermediate Similarity	NPD5135	Approved
0.7115	Intermediate Similarity	NPD5169	Approved
0.7097	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7320	Approved
0.7071	Intermediate Similarity	NPD7640	Approved
0.7071	Intermediate Similarity	NPD7639	Approved
0.7065	Intermediate Similarity	NPD6409	Approved
0.7065	Intermediate Similarity	NPD5280	Approved
0.7065	Intermediate Similarity	NPD6684	Approved
0.7065	Intermediate Similarity	NPD7521	Approved
0.7065	Intermediate Similarity	NPD5330	Approved
0.7065	Intermediate Similarity	NPD7334	Approved
0.7065	Intermediate Similarity	NPD7146	Approved
0.7065	Intermediate Similarity	NPD4694	Approved
0.7048	Intermediate Similarity	NPD5127	Approved
0.7048	Intermediate Similarity	NPD6847	Approved
0.7048	Intermediate Similarity	NPD6617	Approved
0.7048	Intermediate Similarity	NPD6649	Approved
0.7048	Intermediate Similarity	NPD8130	Phase 1
0.7048	Intermediate Similarity	NPD6869	Approved
0.7048	Intermediate Similarity	NPD5217	Approved
0.7048	Intermediate Similarity	NPD5215	Approved
0.7048	Intermediate Similarity	NPD5216	Approved
0.7048	Intermediate Similarity	NPD6650	Approved
0.7045	Intermediate Similarity	NPD4195	Approved
0.7045	Intermediate Similarity	NPD7645	Phase 2
0.7041	Intermediate Similarity	NPD6083	Phase 2
0.7041	Intermediate Similarity	NPD6084	Phase 2
0.7037	Intermediate Similarity	NPD7115	Discovery
0.7019	Intermediate Similarity	NPD6373	Approved
0.7019	Intermediate Similarity	NPD6372	Approved
0.6981	Remote Similarity	NPD8297	Approved
0.6981	Remote Similarity	NPD6882	Approved
0.6916	Remote Similarity	NPD4632	Approved
0.6915	Remote Similarity	NPD5737	Approved
0.6915	Remote Similarity	NPD6903	Approved
0.6915	Remote Similarity	NPD6672	Approved
0.6907	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7900	Approved
0.6905	Remote Similarity	NPD4747	Approved
0.6905	Remote Similarity	NPD4691	Approved
0.6889	Remote Similarity	NPD4692	Approved
0.6889	Remote Similarity	NPD4139	Approved
0.6887	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4519	Discontinued
0.6882	Remote Similarity	NPD4623	Approved
0.6852	Remote Similarity	NPD5167	Approved
0.6847	Remote Similarity	NPD6319	Approved
0.6847	Remote Similarity	NPD6054	Approved
0.6837	Remote Similarity	NPD5695	Phase 3
0.6824	Remote Similarity	NPD6081	Approved
0.6809	Remote Similarity	NPD3573	Approved
0.68	Remote Similarity	NPD5696	Approved
0.68	Remote Similarity	NPD5290	Discontinued
0.68	Remote Similarity	NPD4225	Approved
0.6789	Remote Similarity	NPD6868	Approved
0.6789	Remote Similarity	NPD6274	Approved
0.6786	Remote Similarity	NPD6016	Approved
0.6786	Remote Similarity	NPD4137	Phase 3
0.6786	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6015	Approved
0.6742	Remote Similarity	NPD5364	Discontinued
0.6727	Remote Similarity	NPD6009	Approved
0.6727	Remote Similarity	NPD6317	Approved
0.6726	Remote Similarity	NPD6370	Approved
0.6726	Remote Similarity	NPD5988	Approved
0.6701	Remote Similarity	NPD5284	Approved
0.6701	Remote Similarity	NPD5281	Approved
0.6696	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD4058	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6313	Approved
0.6628	Remote Similarity	NPD5777	Approved
0.6609	Remote Similarity	NPD7492	Approved
0.6607	Remote Similarity	NPD7101	Approved
0.6607	Remote Similarity	NPD7100	Approved
0.6602	Remote Similarity	NPD7632	Discontinued
0.6598	Remote Similarity	NPD4096	Approved
0.6593	Remote Similarity	NPD4748	Discontinued
0.6591	Remote Similarity	NPD3702	Approved
0.6581	Remote Similarity	NPD7736	Approved
0.6571	Remote Similarity	NPD6008	Approved
0.6566	Remote Similarity	NPD6001	Approved
0.6562	Remote Similarity	NPD5208	Approved
0.6552	Remote Similarity	NPD6616	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