NPASS Compound

Structure

NPC471516 OpenBabel07101719522D 26 30 0 0 1 0 0 0 0 0999 V2000 -2.9684 -1.2675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9704 -2.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0190 -1.4434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5906 1.2639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5906 0.2984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7544 1.7466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7544 -0.1844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0077 -0.5771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1122 0.2680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5675 -0.7811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4858 -0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6857 -0.1327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1223 -1.5256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3920 -0.7092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9183 1.2639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7765 -0.9092 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9183 0.2984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 -0.9673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5675 0.7811 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2000 -0.6154 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4858 0.4828 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.5047 -2.2597 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3258 -0.2331 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0210 -1.8775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 26 1 0 0 0 0 3 15 2 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 16 2 0 0 0 0 7 18 2 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 21 1 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 21 1 1 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 19 25 2 0 0 0 0 19 26 1 0 0 0 0 20 22 1 6 0 0 0 20 23 1 0 0 0 0 22 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	353.2
Volume:	370.471
LogP:	3.019
LogD:	2.71
LogS:	-4.642
# Rotatable Bonds:	3
TPSA:	49.77
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.655
Synthetic Accessibility Score:	6.167
Fsp3:	0.591
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:	-5.098
MDCK Permeability:	2.3825017706258222e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.944

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.987
Plasma Protein Binding (PPB):	64.51689910888672%
Volume Distribution (VD):	2.159
Pgp-substrate:	25.139894485473633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.683
CYP2C19-inhibitor:	0.873
CYP2C19-substrate:	0.937
CYP2C9-inhibitor:	0.717
CYP2C9-substrate:	0.316
CYP2D6-inhibitor:	0.268
CYP2D6-substrate:	0.551
CYP3A4-inhibitor:	0.849
CYP3A4-substrate:	0.934

ADMET: Excretion

Clearance (CL):	8.911
Half-life (T1/2):	0.164

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.791
Drug-inuced Liver Injury (DILI):	0.062
AMES Toxicity:	0.949
Rat Oral Acute Toxicity:	0.983
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.02
Carcinogencity:	0.966
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC471516

Natural Product ID:	NPC471516
*Common Name:**	Vincophylline
IUPAC Name:	n.a.
Synonyms:	Vincophylline
Standard InCHIKey:	GELIUKJJIMDVFO-WUDOCDFTSA-N
Standard InCHI:	InChI=1S/C22H27NO3/c1-3-15-13-23-11-10-22-18-7-5-4-6-16(18)12-20(22,23)9-8-17(15)21(22,14-24)19(25)26-2/h3-7,17,24H,8-14H2,1-2H3/b15-3-/t17-,20-,21?,22-/m1/s1
SMILES:	C/C=C1/CN2CC[C@]34C([C@@H]1CC[C@]23Cc1c4cccc1)(CO)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253985
PubChem CID:	44445385
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000020] Fluorenes

*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
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17939738]
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	leaf and stem-bark	Pahang, Malaysia	1996-JUL	PMID[18078327]
NPO19270	Kopsia singapurensis	Species	Apocynaceae	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	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[450524]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[450524]

☑ 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 NPC471516 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	184
0.1-0.2	898
0.2-0.3	2371
0.3-0.4	12160
0.4-0.5	22984
0.5-0.6	3783
0.6-0.7	310
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7324	Intermediate Similarity	NPC169485
0.7324	Intermediate Similarity	NPC291027
0.7324	Intermediate Similarity	NPC84281
0.7324	Intermediate Similarity	NPC317474
0.7324	Intermediate Similarity	NPC213126
0.7	Intermediate Similarity	NPC475427
0.7	Intermediate Similarity	NPC476441
0.698	Remote Similarity	NPC69496
0.6928	Remote Similarity	NPC478140
0.6914	Remote Similarity	NPC52262
0.6884	Remote Similarity	NPC158854
0.6842	Remote Similarity	NPC245836
0.6842	Remote Similarity	NPC233910
0.6807	Remote Similarity	NPC225319
0.6807	Remote Similarity	NPC73644
0.68	Remote Similarity	NPC116057
0.6792	Remote Similarity	NPC475578
0.6776	Remote Similarity	NPC473962
0.6766	Remote Similarity	NPC99632
0.6766	Remote Similarity	NPC282339
0.6713	Remote Similarity	NPC9274
0.6711	Remote Similarity	NPC183722
0.6708	Remote Similarity	NPC212799
0.6707	Remote Similarity	NPC478076
0.6707	Remote Similarity	NPC201424
0.6703	Remote Similarity	NPC475489
0.6687	Remote Similarity	NPC211525
0.6687	Remote Similarity	NPC153694
0.6686	Remote Similarity	NPC476425
0.6667	Remote Similarity	NPC264728
0.6667	Remote Similarity	NPC473297
0.6667	Remote Similarity	NPC142326
0.6667	Remote Similarity	NPC246913
0.6667	Remote Similarity	NPC94751
0.6648	Remote Similarity	NPC476428
0.6647	Remote Similarity	NPC97380
0.6647	Remote Similarity	NPC310403
0.6647	Remote Similarity	NPC148468
0.6647	Remote Similarity	NPC263709
0.6647	Remote Similarity	NPC63210
0.6647	Remote Similarity	NPC243673
0.6647	Remote Similarity	NPC278887
0.6646	Remote Similarity	NPC161069
0.6646	Remote Similarity	NPC57976
0.6645	Remote Similarity	NPC76785
0.6645	Remote Similarity	NPC273907
0.6645	Remote Similarity	NPC293377
0.6645	Remote Similarity	NPC79465
0.6645	Remote Similarity	NPC260045
0.6645	Remote Similarity	NPC90194
0.6645	Remote Similarity	NPC475318
0.6645	Remote Similarity	NPC474787
0.6645	Remote Similarity	NPC118099
0.6645	Remote Similarity	NPC151706
0.6645	Remote Similarity	NPC476102
0.6645	Remote Similarity	NPC474855
0.6645	Remote Similarity	NPC475598
0.6645	Remote Similarity	NPC49577
0.6645	Remote Similarity	NPC474811
0.6645	Remote Similarity	NPC9687
0.6623	Remote Similarity	NPC313663
0.6612	Remote Similarity	NPC221687
0.6607	Remote Similarity	NPC474058
0.6605	Remote Similarity	NPC476757
0.6603	Remote Similarity	NPC208725
0.6599	Remote Similarity	NPC478014
0.6599	Remote Similarity	NPC478015
0.6599	Remote Similarity	NPC478016
0.6597	Remote Similarity	NPC473573
0.6591	Remote Similarity	NPC11149
0.6582	Remote Similarity	NPC243162
0.6579	Remote Similarity	NPC472413
0.6579	Remote Similarity	NPC40488
0.6576	Remote Similarity	NPC97100
0.6576	Remote Similarity	NPC473375
0.6568	Remote Similarity	NPC476750
0.6567	Remote Similarity	NPC226041
0.6547	Remote Similarity	NPC85560
0.6547	Remote Similarity	NPC244933
0.6544	Remote Similarity	NPC128248
0.6544	Remote Similarity	NPC133809
0.6544	Remote Similarity	NPC136810
0.6544	Remote Similarity	NPC225079
0.6541	Remote Similarity	NPC90967
0.6527	Remote Similarity	NPC93343
0.6524	Remote Similarity	NPC470274
0.6519	Remote Similarity	NPC120393
0.6509	Remote Similarity	NPC315368
0.6503	Remote Similarity	NPC94602
0.65	Remote Similarity	NPC476978
0.6493	Remote Similarity	NPC469893
0.6491	Remote Similarity	NPC470069
0.6491	Remote Similarity	NPC52059
0.649	Remote Similarity	NPC474847
0.6486	Remote Similarity	NPC80150
0.6485	Remote Similarity	NPC122590
0.6483	Remote Similarity	NPC188010
0.6481	Remote Similarity	NPC328824
0.6481	Remote Similarity	NPC138775
0.6478	Remote Similarity	NPC239770
0.6474	Remote Similarity	NPC90693
0.6474	Remote Similarity	NPC64897
0.6471	Remote Similarity	NPC221825
0.6467	Remote Similarity	NPC161827
0.6467	Remote Similarity	NPC184195
0.6467	Remote Similarity	NPC166521
0.6467	Remote Similarity	NPC281470
0.6467	Remote Similarity	NPC172769
0.6467	Remote Similarity	NPC124690
0.6467	Remote Similarity	NPC205
0.646	Remote Similarity	NPC5620
0.6456	Remote Similarity	NPC281104
0.6447	Remote Similarity	NPC65310
0.6444	Remote Similarity	NPC469892
0.6444	Remote Similarity	NPC469890
0.6444	Remote Similarity	NPC469891
0.6429	Remote Similarity	NPC29285
0.6429	Remote Similarity	NPC217801
0.642	Remote Similarity	NPC311330
0.6413	Remote Similarity	NPC163578
0.6413	Remote Similarity	NPC108276
0.6402	Remote Similarity	NPC471512
0.6402	Remote Similarity	NPC2501
0.64	Remote Similarity	NPC96901
0.64	Remote Similarity	NPC251212
0.64	Remote Similarity	NPC214626
0.64	Remote Similarity	NPC139085
0.6384	Remote Similarity	NPC476326
0.6382	Remote Similarity	NPC472414
0.6382	Remote Similarity	NPC79698
0.6379	Remote Similarity	NPC476749
0.6375	Remote Similarity	NPC150712
0.6369	Remote Similarity	NPC475962
0.6359	Remote Similarity	NPC40539
0.6358	Remote Similarity	NPC6975
0.6358	Remote Similarity	NPC472415
0.6357	Remote Similarity	NPC471186
0.6353	Remote Similarity	NPC36495
0.6347	Remote Similarity	NPC275839
0.6346	Remote Similarity	NPC42423
0.6341	Remote Similarity	NPC264589
0.6325	Remote Similarity	NPC162104
0.6319	Remote Similarity	NPC314358
0.6316	Remote Similarity	NPC248117
0.6307	Remote Similarity	NPC293255
0.6307	Remote Similarity	NPC181138
0.6307	Remote Similarity	NPC21752
0.6307	Remote Similarity	NPC298851
0.6307	Remote Similarity	NPC276993
0.6307	Remote Similarity	NPC210415
0.6306	Remote Similarity	NPC3202
0.6304	Remote Similarity	NPC105055
0.6304	Remote Similarity	NPC22689
0.6303	Remote Similarity	NPC129666
0.6301	Remote Similarity	NPC472106
0.6296	Remote Similarity	NPC475128
0.6286	Remote Similarity	NPC19136
0.6282	Remote Similarity	NPC130309
0.628	Remote Similarity	NPC44649
0.628	Remote Similarity	NPC260194
0.628	Remote Similarity	NPC145113
0.6279	Remote Similarity	NPC286871
0.6279	Remote Similarity	NPC472120
0.6279	Remote Similarity	NPC472101
0.6277	Remote Similarity	NPC322598
0.6276	Remote Similarity	NPC242957
0.6276	Remote Similarity	NPC206414
0.6276	Remote Similarity	NPC306977
0.6276	Remote Similarity	NPC287055
0.6268	Remote Similarity	NPC21929
0.6266	Remote Similarity	NPC132847
0.6258	Remote Similarity	NPC473922
0.6258	Remote Similarity	NPC209509
0.6258	Remote Similarity	NPC71271
0.6258	Remote Similarity	NPC316008
0.6258	Remote Similarity	NPC313867
0.6257	Remote Similarity	NPC203005
0.6257	Remote Similarity	NPC321211
0.6257	Remote Similarity	NPC235460
0.6257	Remote Similarity	NPC193410
0.6257	Remote Similarity	NPC99043
0.6257	Remote Similarity	NPC218594
0.625	Remote Similarity	NPC68967
0.6242	Remote Similarity	NPC310467
0.623	Remote Similarity	NPC282092
0.6229	Remote Similarity	NPC469462
0.6225	Remote Similarity	NPC202521
0.6224	Remote Similarity	NPC475006
0.6221	Remote Similarity	NPC472102
0.6221	Remote Similarity	NPC309531
0.622	Remote Similarity	NPC262077
0.622	Remote Similarity	NPC262216
0.6216	Remote Similarity	NPC212891
0.6216	Remote Similarity	NPC474059
0.6211	Remote Similarity	NPC153007
0.6211	Remote Similarity	NPC239762
0.6211	Remote Similarity	NPC163392
0.6199	Remote Similarity	NPC61013
0.6199	Remote Similarity	NPC123241
0.6197	Remote Similarity	NPC274089

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 NPC471516 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	128
0.1-0.2	509
0.2-0.3	930
0.3-0.4	2604
0.4-0.5	3702
0.5-0.6	1119
0.6-0.7	150
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7324	Intermediate Similarity	NPD2608	Approved
0.7324	Intermediate Similarity	NPD4215	Approved
0.7324	Intermediate Similarity	NPD4218	Approved
0.7324	Intermediate Similarity	NPD2611	Approved
0.7324	Intermediate Similarity	NPD3131	Approved
0.7324	Intermediate Similarity	NPD3132	Approved
0.7324	Intermediate Similarity	NPD2610	Approved
0.7324	Intermediate Similarity	NPD2609	Approved
0.7324	Intermediate Similarity	NPD4217	Approved
0.7324	Intermediate Similarity	NPD4216	Approved
0.7324	Intermediate Similarity	NPD2612	Approved
0.7246	Intermediate Similarity	NPD4766	Approved
0.7174	Intermediate Similarity	NPD3598	Phase 3
0.7042	Intermediate Similarity	NPD2994	Approved
0.698	Remote Similarity	NPD2613	Approved
0.6972	Remote Similarity	NPD2116	Approved
0.6972	Remote Similarity	NPD2115	Approved
0.6972	Remote Similarity	NPD2117	Pre-registration
0.6897	Remote Similarity	NPD2946	Phase 2
0.6884	Remote Similarity	NPD1752	Approved
0.6884	Remote Similarity	NPD1756	Approved
0.6875	Remote Similarity	NPD3031	Approved
0.6875	Remote Similarity	NPD3030	Approved
0.6875	Remote Similarity	NPD3032	Approved
0.6857	Remote Similarity	NPD2607	Approved
0.6849	Remote Similarity	NPD3529	Phase 2
0.6849	Remote Similarity	NPD5618	Discontinued
0.6842	Remote Similarity	NPD3614	Approved
0.6842	Remote Similarity	NPD4745	Approved
0.6842	Remote Similarity	NPD3087	Approved
0.6842	Remote Similarity	NPD2570	Approved
0.6842	Remote Similarity	NPD3090	Approved
0.6842	Remote Similarity	NPD3088	Approved
0.6842	Remote Similarity	NPD2566	Approved
0.6842	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2573	Approved
0.6842	Remote Similarity	NPD3089	Approved
0.6842	Remote Similarity	NPD3615	Approved
0.6842	Remote Similarity	NPD3616	Approved
0.6842	Remote Similarity	NPD2574	Discontinued
0.6842	Remote Similarity	NPD2571	Approved
0.6842	Remote Similarity	NPD4746	Phase 3
0.6835	Remote Similarity	NPD5927	Discontinued
0.6809	Remote Similarity	NPD2650	Approved
0.6809	Remote Similarity	NPD2652	Approved
0.6806	Remote Similarity	NPD4479	Discontinued
0.6783	Remote Similarity	NPD5162	Approved
0.6759	Remote Similarity	NPD5981	Approved
0.6753	Remote Similarity	NPD4686	Approved
0.6753	Remote Similarity	NPD4685	Phase 3
0.6753	Remote Similarity	NPD4684	Phase 3
0.6736	Remote Similarity	NPD6065	Approved
0.6714	Remote Similarity	NPD3643	Approved
0.6714	Remote Similarity	NPD3644	Approved
0.6714	Remote Similarity	NPD3642	Approved
0.671	Remote Similarity	NPD5725	Approved
0.671	Remote Similarity	NPD6073	Approved
0.6689	Remote Similarity	NPD5759	Approved
0.6688	Remote Similarity	NPD6623	Phase 3
0.6688	Remote Similarity	NPD7511	Approved
0.6688	Remote Similarity	NPD7512	Approved
0.6667	Remote Similarity	NPD6564	Approved
0.6667	Remote Similarity	NPD6563	Approved
0.6667	Remote Similarity	NPD6565	Approved
0.6667	Remote Similarity	NPD4621	Approved
0.6667	Remote Similarity	NPD4619	Approved
0.6645	Remote Similarity	NPD5263	Approved
0.6645	Remote Similarity	NPD4676	Approved
0.6623	Remote Similarity	NPD7714	Approved
0.6623	Remote Similarity	NPD7715	Approved
0.6603	Remote Similarity	NPD8173	Phase 2
0.6603	Remote Similarity	NPD8172	Phase 2
0.6584	Remote Similarity	NPD7295	Approved
0.6581	Remote Similarity	NPD8416	Discontinued
0.6579	Remote Similarity	NPD4177	Approved
0.6579	Remote Similarity	NPD4175	Approved
0.6552	Remote Similarity	NPD4576	Approved
0.6552	Remote Similarity	NPD4574	Approved
0.6547	Remote Similarity	NPD5705	Approved
0.6547	Remote Similarity	NPD5706	Approved
0.6547	Remote Similarity	NPD5704	Approved
0.6538	Remote Similarity	NPD8643	Discontinued
0.6531	Remote Similarity	NPD6993	Approved
0.6531	Remote Similarity	NPD6994	Approved
0.6528	Remote Similarity	NPD1711	Phase 2
0.6525	Remote Similarity	NPD4234	Approved
0.6525	Remote Similarity	NPD4233	Approved
0.6522	Remote Similarity	NPD7487	Discontinued
0.6519	Remote Similarity	NPD3648	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7436	Approved
0.651	Remote Similarity	NPD7437	Approved
0.6507	Remote Similarity	NPD5990	Approved
0.6507	Remote Similarity	NPD5991	Approved
0.6503	Remote Similarity	NPD8165	Discontinued
0.6497	Remote Similarity	NPD7510	Approved
0.6485	Remote Similarity	NPD7606	Phase 3
0.6474	Remote Similarity	NPD5184	Approved
0.6474	Remote Similarity	NPD5182	Approved
0.6474	Remote Similarity	NPD5185	Approved
0.6471	Remote Similarity	NPD3664	Approved
0.6471	Remote Similarity	NPD3663	Approved
0.6471	Remote Similarity	NPD3662	Phase 3
0.6471	Remote Similarity	NPD3661	Approved
0.6467	Remote Similarity	NPD3071	Approved
0.6467	Remote Similarity	NPD3073	Approved
0.6467	Remote Similarity	NPD2584	Suspended
0.6467	Remote Similarity	NPD3072	Approved
0.646	Remote Similarity	NPD2820	Phase 3
0.6456	Remote Similarity	NPD2569	Approved
0.6456	Remote Similarity	NPD2567	Approved
0.6447	Remote Similarity	NPD2625	Approved
0.6447	Remote Similarity	NPD2160	Approved
0.6447	Remote Similarity	NPD2628	Approved
0.6447	Remote Similarity	NPD2627	Approved
0.6447	Remote Similarity	NPD2159	Approved
0.6447	Remote Similarity	NPD2626	Approved
0.642	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD747	Discontinued
0.6408	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4761	Approved
0.64	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4762	Approved
0.6398	Remote Similarity	NPD2365	Approved
0.6397	Remote Similarity	NPD253	Approved
0.6395	Remote Similarity	NPD7522	Discontinued
0.6382	Remote Similarity	NPD5578	Approved
0.6382	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.638	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD4719	Phase 2
0.637	Remote Similarity	NPD4032	Approved
0.637	Remote Similarity	NPD4031	Approved
0.6369	Remote Similarity	NPD6309	Approved
0.6369	Remote Similarity	NPD5296	Approved
0.6369	Remote Similarity	NPD6310	Approved
0.6369	Remote Similarity	NPD6311	Approved
0.6364	Remote Similarity	NPD5204	Approved
0.6358	Remote Similarity	NPD7082	Approved
0.6353	Remote Similarity	NPD7599	Phase 2
0.6352	Remote Similarity	NPD6294	Approved
0.6352	Remote Similarity	NPD6295	Approved
0.6351	Remote Similarity	NPD6343	Approved
0.6351	Remote Similarity	NPD6345	Approved
0.6345	Remote Similarity	NPD1371	Approved
0.6345	Remote Similarity	NPD1374	Approved
0.6345	Remote Similarity	NPD1373	Approved
0.6345	Remote Similarity	NPD1370	Approved
0.6319	Remote Similarity	NPD7259	Approved
0.6319	Remote Similarity	NPD2575	Approved
0.6316	Remote Similarity	NPD7600	Phase 2
0.631	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7478	Approved
0.6291	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD7094	Approved
0.6276	Remote Similarity	NPD6858	Approved
0.6275	Remote Similarity	NPD6792	Phase 3
0.6267	Remote Similarity	NPD5305	Approved
0.6267	Remote Similarity	NPD5306	Approved
0.6267	Remote Similarity	NPD4416	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD7962	Phase 2
0.6242	Remote Similarity	NPD5581	Approved
0.6226	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4620	Approved
0.6218	Remote Similarity	NPD5201	Approved
0.6218	Remote Similarity	NPD4125	Approved
0.6218	Remote Similarity	NPD4617	Approved
0.6218	Remote Similarity	NPD5203	Approved
0.6209	Remote Similarity	NPD4677	Discontinued
0.6204	Remote Similarity	NPD4655	Approved
0.6204	Remote Similarity	NPD4657	Approved
0.6203	Remote Similarity	NPD7086	Phase 2
0.6203	Remote Similarity	NPD5747	Discontinued
0.6194	Remote Similarity	NPD4151	Approved
0.6193	Remote Similarity	NPD7315	Approved
0.6188	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD4806	Approved
0.6184	Remote Similarity	NPD3603	Phase 3
0.6184	Remote Similarity	NPD4807	Approved
0.6182	Remote Similarity	NPD8131	Suspended
0.6178	Remote Similarity	NPD4738	Phase 2
0.6176	Remote Similarity	NPD4094	Approved
0.6173	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD5121	Approved
0.6164	Remote Similarity	NPD5120	Approved
0.6164	Remote Similarity	NPD5119	Approved
0.6159	Remote Similarity	NPD5265	Approved
0.6159	Remote Similarity	NPD5264	Approved
0.6154	Remote Similarity	NPD3637	Approved
0.6154	Remote Similarity	NPD3635	Approved
0.6154	Remote Similarity	NPD3636	Approved
0.6154	Remote Similarity	NPD3626	Phase 3
0.6145	Remote Similarity	NPD6416	Phase 2
0.6143	Remote Similarity	NPD6024	Approved
0.6143	Remote Similarity	NPD6027	Approved
0.6135	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD2617	Discontinued
0.6125	Remote Similarity	NPD3908	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