NPASS Compound

Structure

NPC259626 OpenBabel07101719512D 36 43 0 0 1 0 0 0 0 0999 V2000 -3.5287 -4.1093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9227 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0567 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6167 2.1694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5305 -4.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7575 -1.8611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2435 -1.2826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9793 1.8209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9796 -3.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3802 1.1828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0134 -1.7295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9855 -0.5724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2304 1.9053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8346 -1.5509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5685 -2.5149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7554 -1.0193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2414 -0.4407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6974 1.3724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9814 -3.3943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1906 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1906 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4199 0.6451 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7818 -1.6235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0567 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0921 0.3000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0712 1.3313 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4305 -2.5597 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 -1.4010 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.5340 -4.2887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0567 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 28 1 0 0 0 0 3 28 1 0 0 0 0 4 32 1 0 0 0 0 5 9 1 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 22 1 0 0 0 0 10 18 1 0 0 0 0 11 19 2 0 0 0 0 12 20 2 0 0 0 0 13 21 2 0 0 0 0 14 16 1 0 0 0 0 14 29 1 0 0 0 0 15 17 1 0 0 0 0 16 33 1 0 0 0 0 17 34 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 29 1 0 0 0 0 20 31 1 0 0 0 0 21 23 1 0 0 0 0 21 32 1 0 0 0 0 22 33 1 0 0 0 0 22 35 2 0 0 0 0 23 30 1 0 0 0 0 24 25 1 0 0 0 0 24 34 1 1 0 0 0 25 28 1 0 0 0 0 25 36 1 1 0 0 0 26 30 1 6 0 0 0 26 31 1 0 0 0 0 26 32 1 0 0 0 0 27 29 1 1 0 0 0 27 33 1 0 0 0 0 27 34 1 0 0 0 0 28 36 1 0 0 0 0 29 30 1 1 0 0 0 30 15 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.28
Volume:	502.097
LogP:	4.498
LogD:	3.558
LogS:	-5.464
# Rotatable Bonds:	4
TPSA:	51.35
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	8
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.656
Synthetic Accessibility Score:	6.309
Fsp3:	0.567
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.307
MDCK Permeability:	2.5862564143608324e-05
Pgp-inhibitor:	0.863
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.836
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.752
Plasma Protein Binding (PPB):	77.48905944824219%
Volume Distribution (VD):	2.367
Pgp-substrate:	15.287759780883789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.176
CYP2C19-inhibitor:	0.716
CYP2C19-substrate:	0.936
CYP2C9-inhibitor:	0.705
CYP2C9-substrate:	0.147
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.738
CYP3A4-inhibitor:	0.929
CYP3A4-substrate:	0.858

ADMET: Excretion

Clearance (CL):	7.671
Half-life (T1/2):	0.104

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.692
Drug-inuced Liver Injury (DILI):	0.114
AMES Toxicity:	0.122
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.778
Carcinogencity:	0.735
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.887

Download Data

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

Natural Product: NPC259626

Natural Product ID:	NPC259626
*Common Name:**	Communesin H
IUPAC Name:	n.a.
Synonyms:	Communesin H
Standard InCHIKey:	RMGREFLDMCGIFA-WFMSWEOJSA-N
Standard InCHI:	InChI=1S/C30H36N4O2/c1-5-9-22(35)33-16-14-29-19-11-6-7-12-20(19)31-26-30(29)15-17-34(27(29)33)24(25-28(2,3)36-25)18-10-8-13-21(23(18)30)32(26)4/h6-8,10-13,24-27,31H,5,9,14-17H2,1-4H3/t24-,25+,26+,27+,29-,30-/m1/s1
SMILES:	CCCC(=O)N1CC[C@]23[C@@H]1N1CC[C@]43[C@@H](Nc3c2cccc3)N(c2c4c([C@@H]1[C@@H]1OC1(C)C)ccc2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL524329
PubChem CID:	11190910
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001913] Alpha carbolines

*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
NPO32528	penicillium rivulum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730257]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ID50	>	12.5	ug ml-1	PMID[508817]

☑ 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 NPC259626 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	289
0.1-0.2	1398
0.2-0.3	6727
0.3-0.4	24143
0.4-0.5	6389
0.5-0.6	3238
0.6-0.7	438
0.7-0.8	67
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9939	High Similarity	NPC2933
0.9878	High Similarity	NPC256288
0.9701	High Similarity	NPC473615
0.9643	High Similarity	NPC229484
0.9586	High Similarity	NPC292675
0.8415	Intermediate Similarity	NPC109787
0.8023	Intermediate Similarity	NPC285622
0.7744	Intermediate Similarity	NPC477173
0.7727	Intermediate Similarity	NPC286871
0.7704	Intermediate Similarity	NPC470488
0.7627	Intermediate Similarity	NPC176983
0.7551	Intermediate Similarity	NPC477179
0.7527	Intermediate Similarity	NPC139085
0.7527	Intermediate Similarity	NPC214626
0.7527	Intermediate Similarity	NPC251212
0.7514	Intermediate Similarity	NPC471122
0.7513	Intermediate Similarity	NPC254850
0.7513	Intermediate Similarity	NPC477178
0.7513	Intermediate Similarity	NPC477180
0.7513	Intermediate Similarity	NPC477181
0.75	Intermediate Similarity	NPC29285
0.7487	Intermediate Similarity	NPC470491
0.7487	Intermediate Similarity	NPC471945
0.7487	Intermediate Similarity	NPC471950
0.7487	Intermediate Similarity	NPC475259
0.7475	Intermediate Similarity	NPC477174
0.7475	Intermediate Similarity	NPC470490
0.7472	Intermediate Similarity	NPC68650
0.7472	Intermediate Similarity	NPC309531
0.7472	Intermediate Similarity	NPC472102
0.7458	Intermediate Similarity	NPC113946
0.745	Intermediate Similarity	NPC471951
0.745	Intermediate Similarity	NPC471946
0.7444	Intermediate Similarity	NPC472106
0.7444	Intermediate Similarity	NPC471124
0.7433	Intermediate Similarity	NPC477159
0.7424	Intermediate Similarity	NPC470489
0.7403	Intermediate Similarity	NPC279527
0.7403	Intermediate Similarity	NPC214960
0.736	Intermediate Similarity	NPC222029
0.7354	Intermediate Similarity	NPC307396
0.7337	Intermediate Similarity	NPC473743
0.7337	Intermediate Similarity	NPC177261
0.7333	Intermediate Similarity	NPC472101
0.7333	Intermediate Similarity	NPC472120
0.7327	Intermediate Similarity	NPC475359
0.7327	Intermediate Similarity	NPC191817
0.7323	Intermediate Similarity	NPC471436
0.7318	Intermediate Similarity	NPC276085
0.7277	Intermediate Similarity	NPC285841
0.7243	Intermediate Similarity	NPC242269
0.7241	Intermediate Similarity	NPC264589
0.7238	Intermediate Similarity	NPC99632
0.7238	Intermediate Similarity	NPC282339
0.7219	Intermediate Similarity	NPC260075
0.7202	Intermediate Similarity	NPC473298
0.7202	Intermediate Similarity	NPC105055
0.7202	Intermediate Similarity	NPC22689
0.7175	Intermediate Similarity	NPC66936
0.7165	Intermediate Similarity	NPC25401
0.7158	Intermediate Similarity	NPC159963
0.7157	Intermediate Similarity	NPC162440
0.7143	Intermediate Similarity	NPC85651
0.7118	Intermediate Similarity	NPC471123
0.7098	Intermediate Similarity	NPC181928
0.7088	Intermediate Similarity	NPC225319
0.7083	Intermediate Similarity	NPC476095
0.7077	Intermediate Similarity	NPC276430
0.7053	Intermediate Similarity	NPC473006
0.7049	Intermediate Similarity	NPC472117
0.7026	Intermediate Similarity	NPC128582
0.7022	Intermediate Similarity	NPC473329
0.701	Intermediate Similarity	NPC14994
0.7005	Intermediate Similarity	NPC355
0.7	Intermediate Similarity	NPC248601
0.6983	Remote Similarity	NPC475763
0.6976	Remote Similarity	NPC285192
0.6974	Remote Similarity	NPC284706
0.6973	Remote Similarity	NPC475420
0.6968	Remote Similarity	NPC96901
0.6965	Remote Similarity	NPC138830
0.6965	Remote Similarity	NPC67904
0.6952	Remote Similarity	NPC471197
0.6936	Remote Similarity	NPC469560
0.6931	Remote Similarity	NPC475097
0.6927	Remote Similarity	NPC318086
0.6919	Remote Similarity	NPC471198
0.6907	Remote Similarity	NPC52262
0.6902	Remote Similarity	NPC143457
0.6895	Remote Similarity	NPC203202
0.6895	Remote Similarity	NPC264482
0.689	Remote Similarity	NPC471663
0.6884	Remote Similarity	NPC34717
0.6878	Remote Similarity	NPC473880
0.6878	Remote Similarity	NPC225400
0.6878	Remote Similarity	NPC476425
0.6875	Remote Similarity	NPC11149
0.6853	Remote Similarity	NPC473569
0.6848	Remote Similarity	NPC193410
0.6845	Remote Similarity	NPC472114
0.6845	Remote Similarity	NPC472538
0.6845	Remote Similarity	NPC470786
0.6845	Remote Similarity	NPC472115
0.6845	Remote Similarity	NPC471155
0.6842	Remote Similarity	NPC470548
0.6832	Remote Similarity	NPC106118
0.6829	Remote Similarity	NPC329833
0.6816	Remote Similarity	NPC90967
0.6813	Remote Similarity	NPC478076
0.6812	Remote Similarity	NPC270241
0.6811	Remote Similarity	NPC248117
0.6806	Remote Similarity	NPC320147
0.68	Remote Similarity	NPC243626
0.68	Remote Similarity	NPC230313
0.6793	Remote Similarity	NPC61013
0.6772	Remote Similarity	NPC472118
0.6771	Remote Similarity	NPC186669
0.6761	Remote Similarity	NPC22082
0.6761	Remote Similarity	NPC186284
0.6758	Remote Similarity	NPC470730
0.6758	Remote Similarity	NPC477176
0.6758	Remote Similarity	NPC477175
0.6758	Remote Similarity	NPC470729
0.6742	Remote Similarity	NPC472103
0.6736	Remote Similarity	NPC218594
0.6736	Remote Similarity	NPC6974
0.6736	Remote Similarity	NPC99043
0.6735	Remote Similarity	NPC473007
0.6732	Remote Similarity	NPC473005
0.6727	Remote Similarity	NPC475969
0.6727	Remote Similarity	NPC474877
0.6727	Remote Similarity	NPC475859
0.6722	Remote Similarity	NPC212799
0.672	Remote Similarity	NPC224970
0.672	Remote Similarity	NPC223595
0.672	Remote Similarity	NPC167724
0.6719	Remote Similarity	NPC476441
0.6716	Remote Similarity	NPC221687
0.6705	Remote Similarity	NPC130251
0.67	Remote Similarity	NPC100863
0.6697	Remote Similarity	NPC165743
0.6686	Remote Similarity	NPC252794
0.6684	Remote Similarity	NPC472121
0.6683	Remote Similarity	NPC472539
0.6683	Remote Similarity	NPC470787
0.6683	Remote Similarity	NPC472540
0.6667	Remote Similarity	NPC13367
0.6667	Remote Similarity	NPC36495
0.6667	Remote Similarity	NPC472100
0.6667	Remote Similarity	NPC470485
0.665	Remote Similarity	NPC322621
0.665	Remote Similarity	NPC472542
0.665	Remote Similarity	NPC472541
0.6649	Remote Similarity	NPC321211
0.6649	Remote Similarity	NPC475094
0.6647	Remote Similarity	NPC145754
0.6632	Remote Similarity	NPC33507
0.6619	Remote Similarity	NPC477160
0.6613	Remote Similarity	NPC469428
0.6613	Remote Similarity	NPC123241
0.6605	Remote Similarity	NPC77777
0.6601	Remote Similarity	NPC97100
0.6601	Remote Similarity	NPC473375
0.66	Remote Similarity	NPC473008
0.6598	Remote Similarity	NPC476326
0.6597	Remote Similarity	NPC469915
0.6596	Remote Similarity	NPC469741
0.6596	Remote Similarity	NPC293458
0.6587	Remote Similarity	NPC475915
0.6567	Remote Similarity	NPC470483
0.6558	Remote Similarity	NPC244425
0.6558	Remote Similarity	NPC15384
0.6556	Remote Similarity	NPC311330
0.6553	Remote Similarity	NPC475489
0.6548	Remote Similarity	NPC19679
0.6546	Remote Similarity	NPC129624
0.6545	Remote Similarity	NPC63047
0.6545	Remote Similarity	NPC475248
0.6543	Remote Similarity	NPC201424
0.6538	Remote Similarity	NPC295548
0.6535	Remote Similarity	NPC473004
0.6526	Remote Similarity	NPC159815
0.6522	Remote Similarity	NPC471512
0.6519	Remote Similarity	NPC116519
0.6515	Remote Similarity	NPC97584
0.6515	Remote Similarity	NPC245741
0.6512	Remote Similarity	NPC251936
0.6502	Remote Similarity	NPC477177
0.6488	Remote Similarity	NPC471199
0.648	Remote Similarity	NPC301760
0.6476	Remote Similarity	NPC277350
0.6474	Remote Similarity	NPC313757
0.6468	Remote Similarity	NPC272174
0.6465	Remote Similarity	NPC478157
0.645	Remote Similarity	NPC282092
0.6447	Remote Similarity	NPC286994
0.6445	Remote Similarity	NPC477065
0.6444	Remote Similarity	NPC63279
0.6441	Remote Similarity	NPC267508
0.6438	Remote Similarity	NPC474896

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 NPC259626 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	500
0.2-0.3	706
0.3-0.4	1611
0.4-0.5	3611
0.5-0.6	2360
0.6-0.7	193
0.7-0.8	1
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
0.7086	Intermediate Similarity	NPD7785	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD8240	Discontinued
0.7062	Intermediate Similarity	NPD5942	Approved
0.7062	Intermediate Similarity	NPD5941	Approved
0.7015	Intermediate Similarity	NPD6238	Discontinued
0.6875	Remote Similarity	NPD6879	Phase 2
0.6875	Remote Similarity	NPD6878	Phase 2
0.6868	Remote Similarity	NPD5743	Approved
0.6868	Remote Similarity	NPD5742	Approved
0.6868	Remote Similarity	NPD5741	Approved
0.6859	Remote Similarity	NPD5600	Discontinued
0.6813	Remote Similarity	NPD4120	Approved
0.6813	Remote Similarity	NPD4121	Phase 3
0.6789	Remote Similarity	NPD5997	Discontinued
0.6754	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5318	Discontinued
0.6685	Remote Similarity	NPD5024	Approved
0.6682	Remote Similarity	NPD7824	Approved
0.6667	Remote Similarity	NPD7599	Phase 2
0.6651	Remote Similarity	NPD7271	Approved
0.665	Remote Similarity	NPD6557	Phase 2
0.6631	Remote Similarity	NPD7600	Phase 2
0.6615	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7731	Approved
0.6591	Remote Similarity	NPD6358	Phase 2
0.6591	Remote Similarity	NPD7730	Approved
0.6583	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3625	Discontinued
0.6559	Remote Similarity	NPD7105	Phase 1
0.6545	Remote Similarity	NPD7890	Discontinued
0.6526	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD8630	Approved
0.6514	Remote Similarity	NPD5184	Approved
0.6514	Remote Similarity	NPD5182	Approved
0.6514	Remote Similarity	NPD5185	Approved
0.65	Remote Similarity	NPD4430	Phase 2
0.6491	Remote Similarity	NPD1950	Approved
0.6491	Remote Similarity	NPD1949	Approved
0.6491	Remote Similarity	NPD3240	Phase 2
0.6465	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7791	Approved
0.6444	Remote Similarity	NPD7790	Approved
0.6444	Remote Similarity	NPD7950	Approved
0.6444	Remote Similarity	NPD7952	Approved
0.6444	Remote Similarity	NPD7953	Approved
0.6444	Remote Similarity	NPD7789	Approved
0.6444	Remote Similarity	NPD7951	Approved
0.6444	Remote Similarity	NPD6768	Approved
0.6443	Remote Similarity	NPD7854	Phase 2
0.6441	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6644	Discontinued
0.6409	Remote Similarity	NPD6301	Phase 2
0.6404	Remote Similarity	NPD6342	Discontinued
0.6404	Remote Similarity	NPD6294	Approved
0.6404	Remote Similarity	NPD6295	Approved
0.64	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD2093	Discontinued
0.6387	Remote Similarity	NPD3790	Phase 2
0.6383	Remote Similarity	NPD1663	Discontinued
0.6379	Remote Similarity	NPD4365	Phase 2
0.6379	Remote Similarity	NPD8263	Discontinued
0.6374	Remote Similarity	NPD7487	Discontinued
0.6358	Remote Similarity	NPD5993	Phase 1
0.6355	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD4499	Approved
0.6351	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5060	Phase 1
0.6337	Remote Similarity	NPD6483	Approved
0.6337	Remote Similarity	NPD6484	Approved
0.6335	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7072	Phase 2
0.6324	Remote Similarity	NPD5042	Phase 1
0.6305	Remote Similarity	NPD7444	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD5180	Approved
0.6303	Remote Similarity	NPD5181	Approved
0.6303	Remote Similarity	NPD5179	Approved
0.6295	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6295	Remote Similarity	NPD6978	Phase 2
0.6292	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD3983	Phase 3
0.6287	Remote Similarity	NPD6069	Approved
0.6287	Remote Similarity	NPD6070	Approved
0.6284	Remote Similarity	NPD5918	Discontinued
0.6284	Remote Similarity	NPD2387	Approved
0.6283	Remote Similarity	NPD7688	Phase 1
0.6281	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.627	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD4976	Discontinued
0.6263	Remote Similarity	NPD8060	Phase 1
0.6263	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD5531	Discontinued
0.6256	Remote Similarity	NPD5183	Approved
0.6256	Remote Similarity	NPD5186	Approved
0.625	Remote Similarity	NPD4783	Approved
0.625	Remote Similarity	NPD4781	Approved
0.625	Remote Similarity	NPD7595	Discontinued
0.6244	Remote Similarity	NPD6272	Phase 1
0.6243	Remote Similarity	NPD8128	Discontinued
0.6237	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD7716	Approved
0.6233	Remote Similarity	NPD7717	Approved
0.6231	Remote Similarity	NPD7775	Approved
0.623	Remote Similarity	NPD33	Approved
0.623	Remote Similarity	NPD2820	Phase 3
0.623	Remote Similarity	NPD4393	Approved
0.6223	Remote Similarity	NPD8400	Approved
0.6223	Remote Similarity	NPD8401	Approved
0.6223	Remote Similarity	NPD8402	Approved
0.6216	Remote Similarity	NPD7726	Phase 1
0.6215	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD6345	Approved
0.6213	Remote Similarity	NPD6343	Approved
0.6211	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD2913	Approved
0.6205	Remote Similarity	NPD2914	Approved
0.6197	Remote Similarity	NPD8114	Approved
0.6197	Remote Similarity	NPD8115	Approved
0.6195	Remote Similarity	NPD7780	Approved
0.6195	Remote Similarity	NPD7781	Approved
0.619	Remote Similarity	NPD2790	Discontinued
0.619	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD6995	Phase 1
0.6186	Remote Similarity	NPD7035	Approved
0.6186	Remote Similarity	NPD7036	Phase 3
0.6186	Remote Similarity	NPD4796	Discontinued
0.6183	Remote Similarity	NPD2426	Clinical (unspecified phase)
0.618	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.618	Remote Similarity	NPD7578	Phase 2
0.6178	Remote Similarity	NPD1769	Discontinued
0.6178	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD2365	Approved
0.6162	Remote Similarity	NPD5931	Phase 3
0.6162	Remote Similarity	NPD5933	Phase 3
0.6162	Remote Similarity	NPD5932	Phase 3
0.6162	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD4600	Approved
0.6161	Remote Similarity	NPD4601	Approved
0.6154	Remote Similarity	NPD6037	Discontinued
0.615	Remote Similarity	NPD4644	Clinical (unspecified phase)
0.615	Remote Similarity	NPD4682	Phase 2
0.6146	Remote Similarity	NPD8025	Phase 2
0.6146	Remote Similarity	NPD3388	Phase 1
0.6146	Remote Similarity	NPD4514	Approved
0.6142	Remote Similarity	NPD5633	Discontinued
0.6142	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.614	Remote Similarity	NPD8322	Phase 2
0.6138	Remote Similarity	NPD3248	Phase 1
0.6138	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD7543	Phase 2
0.6135	Remote Similarity	NPD7569	Approved
0.6135	Remote Similarity	NPD7570	Approved
0.6131	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6128	Remote Similarity	NPD7921	Approved
0.6127	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD5581	Approved
0.6122	Remote Similarity	NPD5830	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD2840	Approved
0.6111	Remote Similarity	NPD2791	Discontinued
0.6108	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5086	Approved
0.6105	Remote Similarity	NPD5579	Approved
0.6105	Remote Similarity	NPD5576	Approved
0.6101	Remote Similarity	NPD7470	Discontinued
0.61	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4317	Approved
0.6099	Remote Similarity	NPD7254	Discontinued
0.6098	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD1801	Approved
0.6096	Remote Similarity	NPD1802	Approved
0.6094	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD8016	Phase 3
0.6091	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6566	Discontinued
0.6085	Remote Similarity	NPD8352	Phase 1
0.6084	Remote Similarity	NPD2999	Approved
0.6084	Remote Similarity	NPD3001	Approved
0.6084	Remote Similarity	NPD2039	Approved
0.6084	Remote Similarity	NPD2038	Approved
0.6082	Remote Similarity	NPD19	Approved
0.6082	Remote Similarity	NPD1922	Discontinued
0.6082	Remote Similarity	NPD1742	Approved
0.6082	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD1743	Approved
0.608	Remote Similarity	NPD7940	Phase 3
0.608	Remote Similarity	NPD6259	Discontinued
0.608	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD8167	Discontinued
0.6077	Remote Similarity	NPD6073	Approved
0.6077	Remote Similarity	NPD6544	Discontinued

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