NPASS Compound

Structure

NPC45850 OpenBabel07101718272D 21 23 0 0 1 0 0 0 0 0999 V2000 -0.6501 1.1695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7207 -3.1352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5788 0.2177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.4714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6371 -1.1035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7895 -0.4870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2123 0.0909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0722 -1.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9296 -0.0729 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8608 -1.4387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1410 -0.6105 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6371 -1.1035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6371 -0.3678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6371 -0.3678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7207 -1.8528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2123 -1.5622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0125 -2.4955 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 -1.4637 0.1094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5093 -1.3152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7920 -2.8046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 2 17 1 0 0 0 0 3 11 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 14 1 0 0 0 0 6 10 2 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 6 1 6 0 0 0 9 11 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 6 0 0 0 12 13 2 0 0 0 0 12 16 1 0 0 0 0 13 18 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.13
Volume:	292.168
LogP:	-0.884
LogD:	0.455
LogS:	-2.021
# Rotatable Bonds:	2
TPSA:	82.19
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.766
Synthetic Accessibility Score:	5.241
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.502
MDCK Permeability:	2.425995990051888e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.081
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.22
Plasma Protein Binding (PPB):	41.53949737548828%
Volume Distribution (VD):	0.541
Pgp-substrate:	62.1448974609375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.583
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.076
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.192
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.663

ADMET: Excretion

Clearance (CL):	4.744
Half-life (T1/2):	0.872

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.263
Drug-inuced Liver Injury (DILI):	0.05
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.1
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.851
Carcinogencity:	0.343
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.657

Download Data

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

Natural Product: NPC45850

Natural Product ID:	NPC45850
*Common Name:**	Lycoparin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WGXNRDCZCRXOMJ-YRXQGLPXSA-N
Standard InCHI:	InChI=1S/C16H18N2O3/c1-3-11-9-6-10(15(20)21)8-16(11,17-2)12-4-5-14(19)18-13(12)7-9/h3-6,9,11,17H,1,7-8H2,2H3,(H,18,19)(H,20,21)/t9-,11+,16+/m0/s1
SMILES:	C=C[C@@H]1[C@H]2C=C(C[C@@]1(c1ccc(nc1C2)O)NC)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483513
PubChem CID:	44586220
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000056] Quinolones and derivatives

*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
NPO17043	Lycopodium casuarinoides	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18485717]
NPO17043	Lycopodium casuarinoides	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7931368]
NPO17043	Lycopodium casuarinoides	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17043	Lycopodium casuarinoides	Species	Lycopodiaceae	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

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT914	Individual Protein	Acetylcholinesterase	Bos taurus	IC50	>	200000.0	nM	PMID[508240]

☑ 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 NPC45850 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	320
0.1-0.2	2036
0.2-0.3	9558
0.3-0.4	10766
0.4-0.5	14126
0.5-0.6	3723
0.6-0.7	2053
0.7-0.8	97
0.8-0.85	6
0.85-0.9	8
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9651	High Similarity	NPC183805
0.9064	High Similarity	NPC259545
0.8857	High Similarity	NPC232340
0.8713	High Similarity	NPC32028
0.8655	High Similarity	NPC47298
0.8655	High Similarity	NPC315214
0.8621	High Similarity	NPC126481
0.8605	High Similarity	NPC159319
0.8523	High Similarity	NPC471294
0.8197	Intermediate Similarity	NPC133306
0.8066	Intermediate Similarity	NPC303225
0.7872	Intermediate Similarity	NPC194040
0.7833	Intermediate Similarity	NPC469928
0.7831	Intermediate Similarity	NPC206186
0.7745	Intermediate Similarity	NPC330009
0.7727	Intermediate Similarity	NPC476098
0.759	Intermediate Similarity	NPC276517
0.754	Intermediate Similarity	NPC84347
0.7525	Intermediate Similarity	NPC280714
0.75	Intermediate Similarity	NPC309845
0.7487	Intermediate Similarity	NPC213308
0.7475	Intermediate Similarity	NPC306376
0.7463	Intermediate Similarity	NPC9894
0.7452	Intermediate Similarity	NPC469727
0.7438	Intermediate Similarity	NPC53344
0.7438	Intermediate Similarity	NPC270918
0.7418	Intermediate Similarity	NPC84508
0.7413	Intermediate Similarity	NPC474116
0.7402	Intermediate Similarity	NPC39679
0.74	Intermediate Similarity	NPC315491
0.74	Intermediate Similarity	NPC45459
0.7346	Intermediate Similarity	NPC472099
0.7344	Intermediate Similarity	NPC243058
0.7337	Intermediate Similarity	NPC78767
0.7337	Intermediate Similarity	NPC473814
0.7337	Intermediate Similarity	NPC156704
0.7333	Intermediate Similarity	NPC96321
0.733	Intermediate Similarity	NPC471304
0.7327	Intermediate Similarity	NPC162730
0.7323	Intermediate Similarity	NPC146724
0.7306	Intermediate Similarity	NPC320394
0.7277	Intermediate Similarity	NPC67659
0.7273	Intermediate Similarity	NPC60553
0.7273	Intermediate Similarity	NPC237740
0.7268	Intermediate Similarity	NPC116573
0.7255	Intermediate Similarity	NPC314648
0.7251	Intermediate Similarity	NPC473041
0.725	Intermediate Similarity	NPC90229
0.725	Intermediate Similarity	NPC141454
0.725	Intermediate Similarity	NPC74153
0.7246	Intermediate Similarity	NPC234999
0.7245	Intermediate Similarity	NPC128751
0.7245	Intermediate Similarity	NPC246700
0.7243	Intermediate Similarity	NPC51388
0.7238	Intermediate Similarity	NPC152768
0.7238	Intermediate Similarity	NPC148183
0.7236	Intermediate Similarity	NPC93390
0.7231	Intermediate Similarity	NPC90415
0.7228	Intermediate Similarity	NPC249040
0.7216	Intermediate Similarity	NPC203635
0.7212	Intermediate Similarity	NPC220337
0.7212	Intermediate Similarity	NPC23294
0.7212	Intermediate Similarity	NPC87413
0.7208	Intermediate Similarity	NPC83111
0.7208	Intermediate Similarity	NPC106833
0.7208	Intermediate Similarity	NPC329858
0.7208	Intermediate Similarity	NPC469497
0.7207	Intermediate Similarity	NPC161292
0.7206	Intermediate Similarity	NPC317572
0.7204	Intermediate Similarity	NPC473057
0.72	Intermediate Similarity	NPC245916
0.719	Intermediate Similarity	NPC118228
0.7189	Intermediate Similarity	NPC322644
0.7188	Intermediate Similarity	NPC219336
0.7188	Intermediate Similarity	NPC164340
0.7188	Intermediate Similarity	NPC88363
0.7184	Intermediate Similarity	NPC88008
0.7177	Intermediate Similarity	NPC475778
0.7169	Intermediate Similarity	NPC475720
0.7169	Intermediate Similarity	NPC474192
0.7167	Intermediate Similarity	NPC257142
0.7163	Intermediate Similarity	NPC303951
0.7157	Intermediate Similarity	NPC102338
0.7157	Intermediate Similarity	NPC63199
0.7157	Intermediate Similarity	NPC111602
0.7157	Intermediate Similarity	NPC196251
0.7156	Intermediate Similarity	NPC74969
0.7156	Intermediate Similarity	NPC3207
0.7156	Intermediate Similarity	NPC208522
0.7143	Intermediate Similarity	NPC250448
0.7143	Intermediate Similarity	NPC160381
0.7136	Intermediate Similarity	NPC300156
0.7136	Intermediate Similarity	NPC74360
0.7135	Intermediate Similarity	NPC219848
0.7135	Intermediate Similarity	NPC15573
0.7135	Intermediate Similarity	NPC183662
0.7135	Intermediate Similarity	NPC217372
0.7128	Intermediate Similarity	NPC207851
0.7128	Intermediate Similarity	NPC41717
0.7124	Intermediate Similarity	NPC469734
0.7123	Intermediate Similarity	NPC293151
0.7123	Intermediate Similarity	NPC474701
0.7121	Intermediate Similarity	NPC314333
0.712	Intermediate Similarity	NPC139763
0.7107	Intermediate Similarity	NPC278434
0.7101	Intermediate Similarity	NPC193238
0.7101	Intermediate Similarity	NPC315545
0.7101	Intermediate Similarity	NPC314297
0.71	Intermediate Similarity	NPC473821
0.71	Intermediate Similarity	NPC230403
0.7098	Intermediate Similarity	NPC72980
0.7098	Intermediate Similarity	NPC213468
0.7098	Intermediate Similarity	NPC256268
0.7095	Intermediate Similarity	NPC110182
0.7095	Intermediate Similarity	NPC219087
0.7092	Intermediate Similarity	NPC94943
0.7092	Intermediate Similarity	NPC314002
0.7089	Intermediate Similarity	NPC264285
0.7087	Intermediate Similarity	NPC185742
0.7087	Intermediate Similarity	NPC475847
0.7085	Intermediate Similarity	NPC41679
0.7081	Intermediate Similarity	NPC470020
0.7079	Intermediate Similarity	NPC153042
0.7075	Intermediate Similarity	NPC322064
0.7074	Intermediate Similarity	NPC471178
0.7073	Intermediate Similarity	NPC328596
0.7073	Intermediate Similarity	NPC328318
0.7071	Intermediate Similarity	NPC44354
0.7071	Intermediate Similarity	NPC175474
0.707	Intermediate Similarity	NPC280799
0.7067	Intermediate Similarity	NPC171787
0.7067	Intermediate Similarity	NPC86834
0.7067	Intermediate Similarity	NPC477111
0.7067	Intermediate Similarity	NPC210828
0.7064	Intermediate Similarity	NPC478078
0.7059	Intermediate Similarity	NPC473105
0.7056	Intermediate Similarity	NPC171171
0.7053	Intermediate Similarity	NPC313345
0.7053	Intermediate Similarity	NPC175602
0.7053	Intermediate Similarity	NPC314855
0.7053	Intermediate Similarity	NPC313796
0.7053	Intermediate Similarity	NPC315638
0.7051	Intermediate Similarity	NPC473449
0.705	Intermediate Similarity	NPC99666
0.7049	Intermediate Similarity	NPC284348
0.7049	Intermediate Similarity	NPC153769
0.7048	Intermediate Similarity	NPC294375
0.7047	Intermediate Similarity	NPC111275
0.7041	Intermediate Similarity	NPC204717
0.7041	Intermediate Similarity	NPC190007
0.7039	Intermediate Similarity	NPC165599
0.7039	Intermediate Similarity	NPC98715
0.7039	Intermediate Similarity	NPC134848
0.7035	Intermediate Similarity	NPC144381
0.7035	Intermediate Similarity	NPC5630
0.7033	Intermediate Similarity	NPC271862
0.7033	Intermediate Similarity	NPC61038
0.7032	Intermediate Similarity	NPC311906
0.703	Intermediate Similarity	NPC11445
0.7023	Intermediate Similarity	NPC276657
0.7022	Intermediate Similarity	NPC245657
0.702	Intermediate Similarity	NPC46580
0.7019	Intermediate Similarity	NPC321428
0.7019	Intermediate Similarity	NPC183777
0.7019	Intermediate Similarity	NPC4687
0.7019	Intermediate Similarity	NPC283117
0.7018	Intermediate Similarity	NPC319232
0.7018	Intermediate Similarity	NPC24370
0.7014	Intermediate Similarity	NPC207686
0.7014	Intermediate Similarity	NPC472098
0.7014	Intermediate Similarity	NPC49547
0.701	Intermediate Similarity	NPC241024
0.7009	Intermediate Similarity	NPC184408
0.7005	Intermediate Similarity	NPC322482
0.7005	Intermediate Similarity	NPC475070
0.7	Intermediate Similarity	NPC314834
0.6991	Remote Similarity	NPC60621
0.699	Remote Similarity	NPC212535
0.699	Remote Similarity	NPC220765
0.699	Remote Similarity	NPC19679
0.6986	Remote Similarity	NPC475910
0.6986	Remote Similarity	NPC127677
0.6986	Remote Similarity	NPC258062
0.6981	Remote Similarity	NPC317752
0.6981	Remote Similarity	NPC478074
0.698	Remote Similarity	NPC220151
0.698	Remote Similarity	NPC195239
0.698	Remote Similarity	NPC19692
0.698	Remote Similarity	NPC157828
0.6979	Remote Similarity	NPC474409
0.6979	Remote Similarity	NPC477976
0.6978	Remote Similarity	NPC475816
0.6976	Remote Similarity	NPC79129
0.6976	Remote Similarity	NPC81654
0.6976	Remote Similarity	NPC313985
0.6976	Remote Similarity	NPC49196
0.6976	Remote Similarity	NPC249150
0.6976	Remote Similarity	NPC195461
0.6976	Remote Similarity	NPC329793
0.6974	Remote Similarity	NPC471997

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 NPC45850 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	570
0.2-0.3	726
0.3-0.4	1245
0.4-0.5	2902
0.5-0.6	2628
0.6-0.7	843
0.7-0.8	27
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8655	High Similarity	NPD1685	Approved
0.8655	High Similarity	NPD1684	Approved
0.861	High Similarity	NPD5497	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2916	Discontinued
0.7734	Intermediate Similarity	NPD3243	Approved
0.764	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6376	Discontinued
0.746	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD2844	Phase 3
0.7435	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD5901	Discontinued
0.7411	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD484	Approved
0.7373	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD2177	Approved
0.735	Intermediate Similarity	NPD2176	Approved
0.735	Intermediate Similarity	NPD2175	Phase 3
0.7347	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD7010	Phase 3
0.7282	Intermediate Similarity	NPD4948	Discontinued
0.725	Intermediate Similarity	NPD5003	Discontinued
0.7234	Intermediate Similarity	NPD1325	Approved
0.7234	Intermediate Similarity	NPD1326	Approved
0.7214	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5939	Approved
0.7212	Intermediate Similarity	NPD5936	Approved
0.719	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5416	Discontinued
0.7121	Intermediate Similarity	NPD4499	Approved
0.7107	Intermediate Similarity	NPD2383	Phase 1
0.7087	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5020	Approved
0.705	Intermediate Similarity	NPD6665	Discontinued
0.7049	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6158	Phase 2
0.7047	Intermediate Similarity	NPD6159	Phase 2
0.7043	Intermediate Similarity	NPD6724	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD2564	Approved
0.7035	Intermediate Similarity	NPD2565	Phase 2
0.703	Intermediate Similarity	NPD5512	Phase 3
0.7026	Intermediate Similarity	NPD4204	Approved
0.7026	Intermediate Similarity	NPD3178	Discontinued
0.7026	Intermediate Similarity	NPD4203	Approved
0.7024	Intermediate Similarity	NPD4511	Phase 1
0.7021	Intermediate Similarity	NPD5088	Discontinued
0.7021	Intermediate Similarity	NPD862	Approved
0.7021	Intermediate Similarity	NPD861	Approved
0.7021	Intermediate Similarity	NPD863	Approved
0.7019	Intermediate Similarity	NPD5429	Discontinued
0.7019	Intermediate Similarity	NPD6290	Phase 2
0.7015	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7395	Discontinued
0.7009	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6323	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2382	Approved
0.6995	Remote Similarity	NPD2380	Approved
0.6995	Remote Similarity	NPD2381	Approved
0.6995	Remote Similarity	NPD749	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD925	Approved
0.6984	Remote Similarity	NPD926	Approved
0.6981	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4400	Approved
0.6976	Remote Similarity	NPD4600	Approved
0.6976	Remote Similarity	NPD4601	Approved
0.6974	Remote Similarity	NPD5445	Approved
0.6974	Remote Similarity	NPD5488	Discontinued
0.697	Remote Similarity	NPD3315	Phase 3
0.6967	Remote Similarity	NPD4502	Phase 2
0.6961	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2920	Discontinued
0.6957	Remote Similarity	NPD2882	Phase 1
0.6954	Remote Similarity	NPD2096	Phase 2
0.6954	Remote Similarity	NPD2091	Phase 2
0.6952	Remote Similarity	NPD6529	Discontinued
0.6948	Remote Similarity	NPD5293	Phase 2
0.6948	Remote Similarity	NPD4897	Phase 2
0.6948	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5632	Approved
0.693	Remote Similarity	NPD7878	Phase 2
0.6927	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6999	Discontinued
0.6915	Remote Similarity	NPD2336	Approved
0.6912	Remote Similarity	NPD5506	Approved
0.6912	Remote Similarity	NPD5507	Approved
0.6912	Remote Similarity	NPD7948	Phase 1
0.6909	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5100	Phase 3
0.6904	Remote Similarity	NPD2092	Phase 2
0.6904	Remote Similarity	NPD2095	Phase 2
0.6904	Remote Similarity	NPD2094	Phase 2
0.6897	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD3925	Approved
0.6895	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD750	Phase 2
0.6881	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5937	Approved
0.6878	Remote Similarity	NPD7778	Approved
0.6878	Remote Similarity	NPD7777	Approved
0.6878	Remote Similarity	NPD5014	Discontinued
0.6878	Remote Similarity	NPD53	Approved
0.6875	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6641	Approved
0.6872	Remote Similarity	NPD6642	Approved
0.6869	Remote Similarity	NPD6178	Phase 3
0.6866	Remote Similarity	NPD6242	Discontinued
0.6864	Remote Similarity	NPD3263	Phase 3
0.6862	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD5065	Approved
0.6856	Remote Similarity	NPD482	Approved
0.6853	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3947	Discontinued
0.6842	Remote Similarity	NPD5426	Phase 3
0.6839	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD4889	Approved
0.6833	Remote Similarity	NPD4845	Discontinued
0.6832	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD2510	Approved
0.6825	Remote Similarity	NPD2509	Approved
0.6816	Remote Similarity	NPD7234	Approved
0.6816	Remote Similarity	NPD7233	Approved
0.6812	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4501	Approved
0.6812	Remote Similarity	NPD4500	Approved
0.681	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD6282	Discontinued
0.6804	Remote Similarity	NPD6995	Phase 1
0.6802	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3404	Approved
0.6794	Remote Similarity	NPD4044	Discontinued
0.6784	Remote Similarity	NPD1096	Discontinued
0.6783	Remote Similarity	NPD3962	Phase 2
0.6783	Remote Similarity	NPD3959	Phase 2
0.678	Remote Similarity	NPD2307	Discontinued
0.6776	Remote Similarity	NPD7069	Discontinued
0.6773	Remote Similarity	NPD3222	Phase 2
0.6772	Remote Similarity	NPD5255	Approved
0.6771	Remote Similarity	NPD424	Approved
0.6771	Remote Similarity	NPD425	Approved
0.6771	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6492	Phase 2
0.6763	Remote Similarity	NPD3814	Phase 1
0.6762	Remote Similarity	NPD8282	Approved
0.6762	Remote Similarity	NPD56	Approved
0.6762	Remote Similarity	NPD6987	Phase 1
0.6762	Remote Similarity	NPD8283	Approved
0.6761	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3394	Approved
0.6759	Remote Similarity	NPD3393	Approved
0.6759	Remote Similarity	NPD3389	Approved
0.6758	Remote Similarity	NPD7726	Phase 1
0.6754	Remote Similarity	NPD1631	Approved
0.6751	Remote Similarity	NPD3920	Phase 2
0.675	Remote Similarity	NPD2762	Phase 2
0.6744	Remote Similarity	NPD3795	Approved
0.6744	Remote Similarity	NPD3794	Approved
0.6743	Remote Similarity	NPD3258	Approved
0.6742	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5086	Approved
0.6736	Remote Similarity	NPD2781	Approved
0.6733	Remote Similarity	NPD1534	Approved
0.6732	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.673	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5530	Phase 1
0.6729	Remote Similarity	NPD7470	Discontinued
0.6726	Remote Similarity	NPD2951	Discontinued
0.6724	Remote Similarity	NPD8358	Approved
0.6722	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD2896	Discontinued
0.6719	Remote Similarity	NPD2780	Approved
0.6719	Remote Similarity	NPD2782	Approved
0.6717	Remote Similarity	NPD6452	Discontinued
0.6717	Remote Similarity	NPD5473	Discontinued
0.6716	Remote Similarity	NPD5256	Discontinued
0.6715	Remote Similarity	NPD2727	Phase 2
0.6715	Remote Similarity	NPD4397	Phase 1
0.6714	Remote Similarity	NPD4506	Discontinued
0.6712	Remote Similarity	NPD7603	Discontinued
0.6703	Remote Similarity	NPD4702	Approved
0.6703	Remote Similarity	NPD4703	Approved
0.6701	Remote Similarity	NPD1575	Approved
0.6701	Remote Similarity	NPD1573	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