NPASS Compound

Structure

CID311906 OpenBabel06191716122D 28 32 0 0 1 0 0 0 0 0999 V2000 1.6582 -0.2085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4813 1.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5345 4.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6942 -0.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7493 2.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8832 2.6921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8001 -0.0808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8806 -0.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7718 0.0192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8832 0.6921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1856 1.3570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0181 0.2272 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3288 0.5679 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7493 1.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0662 0.8831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0172 1.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0172 2.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4784 1.6921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1786 0.9839 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8011 -0.0360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1850 2.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4794 1.7370 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0662 2.5012 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1942 -0.9555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1645 2.2826 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6153 0.6921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1300 3.4334 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 17 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 24 1 0 0 0 0 9 12 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 4 1 1 0 0 0 12 19 1 0 0 0 0 13 9 1 6 0 0 0 13 20 1 0 0 0 0 14 27 1 0 0 0 0 15 16 1 0 0 0 0 15 18 2 0 0 0 0 16 17 2 0 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 18 23 1 0 0 0 0 19 22 1 1 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 20 25 2 0 0 0 0 21 26 2 0 0 0 0 21 28 1 0 0 0 0 22 21 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.19
Volume:	387.622
LogP:	3.332
LogD:	3.545
LogS:	-3.995
# Rotatable Bonds:	4
TPSA:	71.63
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.829
Synthetic Accessibility Score:	5.231
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.03
MDCK Permeability:	1.4271041436586529e-05
Pgp-inhibitor:	0.257
Pgp-substrate:	0.662
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.53

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.833
Plasma Protein Binding (PPB):	89.7688980102539%
Volume Distribution (VD):	0.885
Pgp-substrate:	8.412976264953613%

ADMET: Metabolism

CYP1A2-inhibitor:	0.395
CYP1A2-substrate:	0.954
CYP2C19-inhibitor:	0.882
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.642
CYP2C9-substrate:	0.877
CYP2D6-inhibitor:	0.077
CYP2D6-substrate:	0.876
CYP3A4-inhibitor:	0.931
CYP3A4-substrate:	0.888

ADMET: Excretion

Clearance (CL):	9.632
Half-life (T1/2):	0.195

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.646
Drug-inuced Liver Injury (DILI):	0.301
AMES Toxicity:	0.125
Rat Oral Acute Toxicity:	0.933
Maximum Recommended Daily Dose:	0.868
Skin Sensitization:	0.062
Carcinogencity:	0.195
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC311906

Natural Product ID:	NPC311906
*Common Name:**	LTQINICYLGNLHN-IMDACWRGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LTQINICYLGNLHN-IMDACWRGSA-N
Standard InCHI:	InChI=1S/C22H26N2O4/c1-4-12-9-13-11-22(21(26)28-3)18-15(7-8-24(19(12)22)20(13)25)16-10-14(27-2)5-6-17(16)23-18/h5-6,10,12-13,19,23H,4,7-9,11H2,1-3H3/t12-,13+,19-,22+/m0/s1
SMILES:	CC[C@H]1C[C@@H]2C[C@@]3([C@H]1N(C2=O)CCc1c3[nH]c2c1cc(cc2)OC)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3325765
PubChem CID:	12110672
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002748] Ibogan-type alkaloids

*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
NPO23773	Holacantha emoryi	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23978	Dorstenia zenkeri	Species	Moraceae	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
EC50	2
IC50	1
Others	2

Activity Type	# Activity
Individual Protein	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1885	Individual Protein	Transient receptor potential cation channel subfamily M member 8	Mus musculus	IC50	>	100000.0	nM	PMID[507106]
NPT346	Individual Protein	Transient receptor potential cation channel subfamily A member 1	Homo sapiens	Activity	=	49.0	%	PMID[507106]
NPT346	Individual Protein	Transient receptor potential cation channel subfamily A member 1	Homo sapiens	EC50	=	78000.0	nM	PMID[507106]
NPT472	Individual Protein	Vanilloid receptor	Homo sapiens	Activity	=	59.0	%	PMID[507106]
NPT472	Individual Protein	Vanilloid receptor	Homo sapiens	EC50	=	30000.0	nM	PMID[507106]

☑ 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 NPC311906 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	465
0.1-0.2	2166
0.2-0.3	9898
0.3-0.4	9647
0.4-0.5	14627
0.5-0.6	3217
0.6-0.7	2143
0.7-0.8	453
0.8-0.85	46
0.85-0.9	24
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9458	High Similarity	NPC96321
0.939	High Similarity	NPC475816
0.9108	High Similarity	NPC475720
0.9108	High Similarity	NPC474192
0.902	High Similarity	NPC471304
0.899	High Similarity	NPC473041
0.892	High Similarity	NPC478078
0.8894	High Similarity	NPC469928
0.8802	High Similarity	NPC473105
0.8762	High Similarity	NPC329793
0.8705	High Similarity	NPC17437
0.861	High Similarity	NPC473540
0.8565	High Similarity	NPC477066
0.8551	High Similarity	NPC472099
0.8538	High Similarity	NPC148183
0.8538	High Similarity	NPC152768
0.8527	High Similarity	NPC478082
0.8527	High Similarity	NPC478081
0.8527	High Similarity	NPC477067
0.8451	Intermediate Similarity	NPC81939
0.8451	Intermediate Similarity	NPC330009
0.8414	Intermediate Similarity	NPC475666
0.8411	Intermediate Similarity	NPC305984
0.8398	Intermediate Similarity	NPC478080
0.8396	Intermediate Similarity	NPC472098
0.8311	Intermediate Similarity	NPC21638
0.8276	Intermediate Similarity	NPC329982
0.8227	Intermediate Similarity	NPC329858
0.8221	Intermediate Similarity	NPC329747
0.8208	Intermediate Similarity	NPC475910
0.8199	Intermediate Similarity	NPC300156
0.8186	Intermediate Similarity	NPC478074
0.8153	Intermediate Similarity	NPC157931
0.8137	Intermediate Similarity	NPC314333
0.8051	Intermediate Similarity	NPC478083
0.7972	Intermediate Similarity	NPC162730
0.7955	Intermediate Similarity	NPC303658
0.7948	Intermediate Similarity	NPC184680
0.7944	Intermediate Similarity	NPC45190
0.7928	Intermediate Similarity	NPC280799
0.7913	Intermediate Similarity	NPC470784
0.7913	Intermediate Similarity	NPC470785
0.7887	Intermediate Similarity	NPC474116
0.7885	Intermediate Similarity	NPC55493
0.785	Intermediate Similarity	NPC476098
0.7843	Intermediate Similarity	NPC176127
0.7826	Intermediate Similarity	NPC63199
0.7826	Intermediate Similarity	NPC196251
0.7826	Intermediate Similarity	NPC111602
0.7826	Intermediate Similarity	NPC102338
0.7824	Intermediate Similarity	NPC4687
0.781	Intermediate Similarity	NPC276517
0.7808	Intermediate Similarity	NPC264176
0.7797	Intermediate Similarity	NPC194740
0.7797	Intermediate Similarity	NPC471762
0.7778	Intermediate Similarity	NPC277350
0.7742	Intermediate Similarity	NPC270918
0.7742	Intermediate Similarity	NPC53344
0.7742	Intermediate Similarity	NPC321428
0.7742	Intermediate Similarity	NPC471303
0.7719	Intermediate Similarity	NPC66777
0.771	Intermediate Similarity	NPC254240
0.771	Intermediate Similarity	NPC199851
0.771	Intermediate Similarity	NPC249040
0.771	Intermediate Similarity	NPC312870
0.771	Intermediate Similarity	NPC294909
0.771	Intermediate Similarity	NPC128265
0.7708	Intermediate Similarity	NPC303374
0.7692	Intermediate Similarity	NPC39500
0.7689	Intermediate Similarity	NPC60621
0.7682	Intermediate Similarity	NPC87413
0.7675	Intermediate Similarity	NPC257851
0.7672	Intermediate Similarity	NPC477549
0.7668	Intermediate Similarity	NPC169402
0.7667	Intermediate Similarity	NPC92111
0.7664	Intermediate Similarity	NPC241024
0.7654	Intermediate Similarity	NPC191489
0.7647	Intermediate Similarity	NPC475778
0.7644	Intermediate Similarity	NPC323969
0.7634	Intermediate Similarity	NPC46561
0.7619	Intermediate Similarity	NPC472112
0.7619	Intermediate Similarity	NPC76748
0.7615	Intermediate Similarity	NPC472111
0.7613	Intermediate Similarity	NPC284685
0.7602	Intermediate Similarity	NPC208284
0.7602	Intermediate Similarity	NPC315634
0.7602	Intermediate Similarity	NPC100734
0.7602	Intermediate Similarity	NPC88923
0.7594	Intermediate Similarity	NPC307963
0.7594	Intermediate Similarity	NPC203972
0.758	Intermediate Similarity	NPC249583
0.7578	Intermediate Similarity	NPC116238
0.7577	Intermediate Similarity	NPC144452
0.7577	Intermediate Similarity	NPC280272
0.7576	Intermediate Similarity	NPC474688
0.7571	Intermediate Similarity	NPC296527
0.7559	Intermediate Similarity	NPC131017
0.7559	Intermediate Similarity	NPC260909
0.7557	Intermediate Similarity	NPC234999
0.7556	Intermediate Similarity	NPC184408
0.7554	Intermediate Similarity	NPC39370
0.7547	Intermediate Similarity	NPC472113
0.7546	Intermediate Similarity	NPC214428
0.7546	Intermediate Similarity	NPC213308
0.7546	Intermediate Similarity	NPC176538
0.7543	Intermediate Similarity	NPC473186
0.7535	Intermediate Similarity	NPC52557
0.7534	Intermediate Similarity	NPC471080
0.7534	Intermediate Similarity	NPC469592
0.7524	Intermediate Similarity	NPC21425
0.7523	Intermediate Similarity	NPC223427
0.7523	Intermediate Similarity	NPC162484
0.7523	Intermediate Similarity	NPC245916
0.7522	Intermediate Similarity	NPC288987
0.7512	Intermediate Similarity	NPC472210
0.7512	Intermediate Similarity	NPC269886
0.7512	Intermediate Similarity	NPC247735
0.7512	Intermediate Similarity	NPC472295
0.7512	Intermediate Similarity	NPC81802
0.7511	Intermediate Similarity	NPC469743
0.7489	Intermediate Similarity	NPC185742
0.7489	Intermediate Similarity	NPC174760
0.7489	Intermediate Similarity	NPC475847
0.7489	Intermediate Similarity	NPC274640
0.7478	Intermediate Similarity	NPC469594
0.7478	Intermediate Similarity	NPC24370
0.7478	Intermediate Similarity	NPC319232
0.7477	Intermediate Similarity	NPC220151
0.7477	Intermediate Similarity	NPC19692
0.747	Intermediate Similarity	NPC195788
0.747	Intermediate Similarity	NPC237901
0.7466	Intermediate Similarity	NPC39679
0.7465	Intermediate Similarity	NPC45459
0.7465	Intermediate Similarity	NPC138830
0.7465	Intermediate Similarity	NPC315491
0.7464	Intermediate Similarity	NPC84478
0.7454	Intermediate Similarity	NPC306376
0.7446	Intermediate Similarity	NPC34580
0.7446	Intermediate Similarity	NPC124920
0.7446	Intermediate Similarity	NPC261251
0.7446	Intermediate Similarity	NPC118559
0.7446	Intermediate Similarity	NPC304307
0.7445	Intermediate Similarity	NPC74360
0.7444	Intermediate Similarity	NPC187501
0.7442	Intermediate Similarity	NPC251090
0.7438	Intermediate Similarity	NPC133609
0.7432	Intermediate Similarity	NPC476116
0.7421	Intermediate Similarity	NPC477065
0.7414	Intermediate Similarity	NPC100547
0.7411	Intermediate Similarity	NPC308137
0.7411	Intermediate Similarity	NPC94157
0.7411	Intermediate Similarity	NPC310211
0.7407	Intermediate Similarity	NPC189079
0.7406	Intermediate Similarity	NPC175474
0.7403	Intermediate Similarity	NPC214142
0.7397	Intermediate Similarity	NPC474077
0.7395	Intermediate Similarity	NPC474121
0.7395	Intermediate Similarity	NPC475844
0.7393	Intermediate Similarity	NPC160381
0.7387	Intermediate Similarity	NPC82548
0.7385	Intermediate Similarity	NPC249150
0.7385	Intermediate Similarity	NPC79129
0.7385	Intermediate Similarity	NPC49196
0.7385	Intermediate Similarity	NPC195461
0.7385	Intermediate Similarity	NPC81654
0.7385	Intermediate Similarity	NPC313985
0.7384	Intermediate Similarity	NPC474183
0.7384	Intermediate Similarity	NPC82472
0.7382	Intermediate Similarity	NPC322135
0.7382	Intermediate Similarity	NPC223409
0.7382	Intermediate Similarity	NPC95240
0.738	Intermediate Similarity	NPC198503
0.7378	Intermediate Similarity	NPC74562
0.7378	Intermediate Similarity	NPC316181
0.7378	Intermediate Similarity	NPC151781
0.7376	Intermediate Similarity	NPC475841
0.7376	Intermediate Similarity	NPC474145
0.7373	Intermediate Similarity	NPC100863
0.7368	Intermediate Similarity	NPC208084
0.7362	Intermediate Similarity	NPC284888
0.735	Intermediate Similarity	NPC14288
0.735	Intermediate Similarity	NPC260434
0.7345	Intermediate Similarity	NPC118228
0.7342	Intermediate Similarity	NPC193777
0.7342	Intermediate Similarity	NPC15801
0.7342	Intermediate Similarity	NPC88008
0.7336	Intermediate Similarity	NPC128115
0.7336	Intermediate Similarity	NPC150239
0.7336	Intermediate Similarity	NPC225279
0.7331	Intermediate Similarity	NPC253675
0.733	Intermediate Similarity	NPC285558
0.7327	Intermediate Similarity	NPC156704
0.7319	Intermediate Similarity	NPC321592
0.7319	Intermediate Similarity	NPC54803
0.7316	Intermediate Similarity	NPC122436
0.7313	Intermediate Similarity	NPC74969
0.7311	Intermediate Similarity	NPC41679
0.7311	Intermediate Similarity	NPC131486
0.7306	Intermediate Similarity	NPC244543
0.7294	Intermediate Similarity	NPC50503

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 NPC311906 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	589
0.2-0.3	788
0.3-0.4	1446
0.4-0.5	2708
0.5-0.6	2331
0.6-0.7	887
0.7-0.8	150
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8705	High Similarity	NPD8358	Approved
0.8621	High Similarity	NPD4118	Clinical (unspecified phase)
0.8251	Intermediate Similarity	NPD4885	Approved
0.8137	Intermediate Similarity	NPD4499	Approved
0.7844	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD5293	Phase 2
0.7812	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD5658	Approved
0.7745	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD8016	Phase 3
0.7725	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD6242	Discontinued
0.771	Intermediate Similarity	NPD4501	Approved
0.771	Intermediate Similarity	NPD4500	Approved
0.7658	Intermediate Similarity	NPD3257	Approved
0.7654	Intermediate Similarity	NPD7708	Approved
0.7647	Intermediate Similarity	NPD4558	Phase 2
0.7642	Intermediate Similarity	NPD4418	Discontinued
0.7613	Intermediate Similarity	NPD7955	Approved
0.7613	Intermediate Similarity	NPD7956	Approved
0.7602	Intermediate Similarity	NPD7803	Approved
0.76	Intermediate Similarity	NPD3258	Approved
0.7594	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD1038	Approved
0.7593	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD8463	Approved
0.7589	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD8364	Approved
0.7581	Intermediate Similarity	NPD8363	Approved
0.7569	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD8460	Approved
0.7559	Intermediate Similarity	NPD8459	Approved
0.7543	Intermediate Similarity	NPD7797	Approved
0.7543	Intermediate Similarity	NPD7796	Approved
0.7535	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4952	Phase 3
0.7532	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD5559	Phase 2
0.7478	Intermediate Similarity	NPD5632	Approved
0.7477	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD8465	Approved
0.747	Intermediate Similarity	NPD8466	Approved
0.747	Intermediate Similarity	NPD8467	Approved
0.7466	Intermediate Similarity	NPD6376	Discontinued
0.7466	Intermediate Similarity	NPD2916	Discontinued
0.7465	Intermediate Similarity	NPD484	Approved
0.7436	Intermediate Similarity	NPD4373	Phase 2
0.7427	Intermediate Similarity	NPD8102	Discontinued
0.7426	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD4897	Phase 2
0.7395	Intermediate Similarity	NPD6790	Phase 1
0.7385	Intermediate Similarity	NPD4600	Approved
0.7385	Intermediate Similarity	NPD4601	Approved
0.7373	Intermediate Similarity	NPD3006	Discontinued
0.7371	Intermediate Similarity	NPD4328	Approved
0.7364	Intermediate Similarity	NPD6176	Phase 1
0.7358	Intermediate Similarity	NPD8091	Phase 3
0.7354	Intermediate Similarity	NPD8425	Approved
0.7354	Intermediate Similarity	NPD8426	Approved
0.7353	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD5014	Discontinued
0.7333	Intermediate Similarity	NPD8428	Approved
0.7333	Intermediate Similarity	NPD8429	Approved
0.7333	Intermediate Similarity	NPD8427	Approved
0.7325	Intermediate Similarity	NPD5482	Discontinued
0.7325	Intermediate Similarity	NPD3354	Phase 2
0.7313	Intermediate Similarity	NPD3393	Approved
0.7313	Intermediate Similarity	NPD3394	Approved
0.7313	Intermediate Similarity	NPD3389	Approved
0.7293	Intermediate Similarity	NPD6770	Approved
0.7292	Intermediate Similarity	NPD6517	Phase 3
0.7289	Intermediate Similarity	NPD7470	Discontinued
0.7277	Intermediate Similarity	NPD4506	Discontinued
0.7273	Intermediate Similarity	NPD8100	Phase 3
0.7265	Intermediate Similarity	NPD7452	Approved
0.7265	Intermediate Similarity	NPD7453	Approved
0.7252	Intermediate Similarity	NPD4795	Phase 2
0.7249	Intermediate Similarity	NPD4429	Discontinued
0.7248	Intermediate Similarity	NPD5003	Discontinued
0.7243	Intermediate Similarity	NPD6276	Discontinued
0.7232	Intermediate Similarity	NPD2510	Approved
0.7232	Intermediate Similarity	NPD2509	Approved
0.7229	Intermediate Similarity	NPD5507	Approved
0.7229	Intermediate Similarity	NPD5506	Approved
0.722	Intermediate Similarity	NPD6716	Phase 1
0.722	Intermediate Similarity	NPD3003	Approved
0.7215	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5416	Discontinued
0.7202	Intermediate Similarity	NPD5488	Discontinued
0.7202	Intermediate Similarity	NPD5512	Phase 3
0.7197	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7222	Phase 2
0.7185	Intermediate Similarity	NPD6964	Approved
0.7185	Intermediate Similarity	NPD6963	Approved
0.7184	Intermediate Similarity	NPD8101	Phase 3
0.7179	Intermediate Similarity	NPD7603	Discontinued
0.7175	Intermediate Similarity	NPD3947	Discontinued
0.7174	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5612	Discontinued
0.7161	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD2187	Approved
0.7156	Intermediate Similarity	NPD2189	Approved
0.7149	Intermediate Similarity	NPD1739	Approved
0.7149	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD1740	Approved
0.7143	Intermediate Similarity	NPD5601	Phase 2
0.7143	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD7284	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6209	Approved
0.7118	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5429	Discontinued
0.7106	Intermediate Similarity	NPD7426	Phase 1
0.7105	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD1768	Approved
0.7098	Intermediate Similarity	NPD4035	Approved
0.7098	Intermediate Similarity	NPD4037	Approved
0.7098	Intermediate Similarity	NPD4034	Approved
0.7098	Intermediate Similarity	NPD4122	Approved
0.7098	Intermediate Similarity	NPD4038	Approved
0.7098	Intermediate Similarity	NPD32	Approved
0.7098	Intermediate Similarity	NPD4036	Approved
0.7098	Intermediate Similarity	NPD31	Approved
0.7098	Intermediate Similarity	NPD4039	Approved
0.7098	Intermediate Similarity	NPD4033	Approved
0.7093	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7994	Phase 2
0.7074	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD4368	Phase 2
0.7052	Intermediate Similarity	NPD8489	Phase 1
0.7051	Intermediate Similarity	NPD2564	Approved
0.7051	Intermediate Similarity	NPD2565	Phase 2
0.7043	Intermediate Similarity	NPD5902	Approved
0.7043	Intermediate Similarity	NPD5903	Approved
0.7039	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7069	Discontinued
0.7027	Intermediate Similarity	NPD3825	Phase 3
0.7026	Intermediate Similarity	NPD6568	Discontinued
0.7022	Intermediate Similarity	NPD5901	Discontinued
0.7017	Intermediate Similarity	NPD5479	Discontinued
0.7012	Intermediate Similarity	NPD7853	Phase 2
0.7004	Intermediate Similarity	NPD3259	Approved
0.7004	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD4154	Approved
0.7	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD7194	Discontinued
0.6992	Remote Similarity	NPD8359	Phase 2
0.6992	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5256	Discontinued
0.6991	Remote Similarity	NPD5530	Phase 1
0.6991	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD3507	Phase 2
0.6987	Remote Similarity	NPD7688	Phase 1
0.698	Remote Similarity	NPD5450	Discontinued
0.6974	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7417	Discontinued
0.6966	Remote Similarity	NPD5930	Phase 3
0.6964	Remote Similarity	NPD7868	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4203	Approved
0.6963	Remote Similarity	NPD4204	Approved
0.6958	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6530	Approved
0.6957	Remote Similarity	NPD3816	Phase 1
0.6957	Remote Similarity	NPD6228	Discontinued
0.6957	Remote Similarity	NPD3815	Phase 1
0.6957	Remote Similarity	NPD6531	Approved
0.6955	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD7395	Discontinued
0.6952	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5022	Discontinued
0.6941	Remote Similarity	NPD5913	Phase 3
0.6941	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD2844	Phase 3
0.6937	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD3243	Approved
0.6926	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3402	Phase 1
0.6923	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4602	Approved
0.6916	Remote Similarity	NPD8403	Phase 1
0.6913	Remote Similarity	NPD4502	Phase 2
0.6907	Remote Similarity	NPD6995	Phase 1
0.6905	Remote Similarity	NPD6961	Discontinued
0.6905	Remote Similarity	NPD8255	Phase 2
0.6892	Remote Similarity	NPD6550	Discontinued
0.6891	Remote Similarity	NPD3263	Phase 3
0.6889	Remote Similarity	NPD6238	Discontinued
0.6888	Remote Similarity	NPD5015	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