NPASS Compound

Structure

NPC244087 OpenBabel07101718202D 24 24 0 0 0 0 0 0 0 0999 V2000 4.2731 6.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2731 7.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4071 6.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4071 8.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4071 5.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5411 7.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5411 4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5411 6.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5411 3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 6.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 3.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 5.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 2.5878 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 0.1280 -2.6736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 18 1 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 16 20 2 0 0 0 0 17 21 2 0 0 0 0 18 22 3 0 0 0 0 19 21 1 0 0 0 0 19 24 2 0 0 0 0 20 23 1 0 0 0 0 21 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.27
Volume:	380.817
LogP:	6.928
LogD:	4.055
LogS:	-5.452
# Rotatable Bonds:	16
TPSA:	56.65
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.283
Synthetic Accessibility Score:	2.601
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.04
MDCK Permeability:	2.0838375348830596e-05
Pgp-inhibitor:	0.071
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.975
30% Bioavailability (F30%):	0.898

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.484
Plasma Protein Binding (PPB):	97.46983337402344%
Volume Distribution (VD):	2.499
Pgp-substrate:	0.8881475925445557%

ADMET: Metabolism

CYP1A2-inhibitor:	0.408
CYP1A2-substrate:	0.183
CYP2C19-inhibitor:	0.519
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.207
CYP2C9-substrate:	0.973
CYP2D6-inhibitor:	0.253
CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.377
CYP3A4-substrate:	0.049

ADMET: Excretion

Clearance (CL):	3.465
Half-life (T1/2):	0.294

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.114
Drug-inuced Liver Injury (DILI):	0.141
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.104
Maximum Recommended Daily Dose:	0.677
Skin Sensitization:	0.943
Carcinogencity:	0.236
Eye Corrosion:	0.907
Eye Irritation:	0.977
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC244087

Natural Product ID:	NPC244087
*Common Name:**	Mycalenitrile 13
IUPAC Name:	16-(5-formyl-1H-pyrrol-2-yl)hexadecanenitrile
Synonyms:	Mycalenitrile 13
Standard InCHIKey:	CGYVXGBLZXYHLD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H34N2O/c22-18-14-12-10-8-6-4-2-1-3-5-7-9-11-13-15-20-16-17-21(19-24)23-20/h16-17,19,23H,1-15H2
SMILES:	C(CCCCCCCC#N)CCCCCCCc1ccc(C=O)[nH]1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1081170
PubChem CID:	44604945
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000124] Aldehydes [CHEMONTID:0003213] Aryl-aldehydes

*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
NPO32868	Mycale sp.	Species	Mycalidae	Eukaryota	n.a.	New Zealand	n.a.	PMID[10843597]
NPO32868	Mycale sp.	Species	Mycalidae	Eukaryota	n.a.	Thai	n.a.	PMID[12608869]
NPO32868	Mycale sp.	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19845338]
NPO32868	Mycale sp.	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	PMID[31833368]
NPO32868	Mycale sp.	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599273]

☑ 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
PROTEIN FAMILY	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	10000.0	nM	PMID[565695]

☑ 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 NPC244087 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	650
0.1-0.2	9203
0.2-0.3	21426
0.3-0.4	6531
0.4-0.5	2720
0.5-0.6	1667
0.6-0.7	443
0.7-0.8	29
0.8-0.85	2
0.85-0.9	0
0.9-0.95	5
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC286529
1.0	High Similarity	NPC169308
1.0	High Similarity	NPC12831
1.0	High Similarity	NPC48171
1.0	High Similarity	NPC129753
1.0	High Similarity	NPC205604
1.0	High Similarity	NPC302717
1.0	High Similarity	NPC74928
1.0	High Similarity	NPC77582
1.0	High Similarity	NPC97230
1.0	High Similarity	NPC209281
1.0	High Similarity	NPC59839
1.0	High Similarity	NPC3698
0.9549	High Similarity	NPC195704
0.9549	High Similarity	NPC138596
0.9549	High Similarity	NPC14448
0.9549	High Similarity	NPC292434
0.9549	High Similarity	NPC64661
0.9549	High Similarity	NPC98156
0.9549	High Similarity	NPC200397
0.9549	High Similarity	NPC167200
0.9203	High Similarity	NPC114033
0.9203	High Similarity	NPC58268
0.9203	High Similarity	NPC129412
0.9203	High Similarity	NPC101130
0.8112	Intermediate Similarity	NPC23215
0.7829	Intermediate Similarity	NPC13432
0.7756	Intermediate Similarity	NPC76982
0.774	Intermediate Similarity	NPC291517
0.7724	Intermediate Similarity	NPC20021
0.7635	Intermediate Similarity	NPC472288
0.7551	Intermediate Similarity	NPC150592
0.7517	Intermediate Similarity	NPC71236
0.7407	Intermediate Similarity	NPC115232
0.7329	Intermediate Similarity	NPC313823
0.729	Intermediate Similarity	NPC260041
0.7289	Intermediate Similarity	NPC252572
0.7202	Intermediate Similarity	NPC151635
0.7195	Intermediate Similarity	NPC42372
0.7169	Intermediate Similarity	NPC471943
0.711	Intermediate Similarity	NPC133003
0.7107	Intermediate Similarity	NPC471655
0.7093	Intermediate Similarity	NPC102755
0.7091	Intermediate Similarity	NPC71132
0.7076	Intermediate Similarity	NPC477042
0.7076	Intermediate Similarity	NPC88110
0.7073	Intermediate Similarity	NPC214106
0.7052	Intermediate Similarity	NPC477003
0.7041	Intermediate Similarity	NPC293216
0.7017	Intermediate Similarity	NPC472296
0.7017	Intermediate Similarity	NPC472297
0.6988	Remote Similarity	NPC233380
0.6959	Remote Similarity	NPC284775
0.6951	Remote Similarity	NPC474492
0.6949	Remote Similarity	NPC324091
0.6928	Remote Similarity	NPC206148
0.6897	Remote Similarity	NPC117027
0.6897	Remote Similarity	NPC159125
0.6872	Remote Similarity	NPC472292
0.6871	Remote Similarity	NPC33229
0.6851	Remote Similarity	NPC472293
0.6839	Remote Similarity	NPC470677
0.6833	Remote Similarity	NPC269886
0.6833	Remote Similarity	NPC247735
0.6833	Remote Similarity	NPC472295
0.6833	Remote Similarity	NPC81802
0.6833	Remote Similarity	NPC472210
0.6831	Remote Similarity	NPC477045
0.6826	Remote Similarity	NPC271797
0.6826	Remote Similarity	NPC21174
0.6824	Remote Similarity	NPC262338
0.6816	Remote Similarity	NPC476460
0.6807	Remote Similarity	NPC100104
0.6807	Remote Similarity	NPC470680
0.6798	Remote Similarity	NPC209917
0.6786	Remote Similarity	NPC2414
0.6784	Remote Similarity	NPC161861
0.677	Remote Similarity	NPC100726
0.6758	Remote Similarity	NPC102592
0.6758	Remote Similarity	NPC79356
0.6743	Remote Similarity	NPC191415
0.674	Remote Similarity	NPC304203
0.6727	Remote Similarity	NPC142688
0.6725	Remote Similarity	NPC54214
0.6705	Remote Similarity	NPC470205
0.6704	Remote Similarity	NPC473666
0.6689	Remote Similarity	NPC41174
0.6687	Remote Similarity	NPC473878
0.6687	Remote Similarity	NPC52110
0.6686	Remote Similarity	NPC80528
0.6685	Remote Similarity	NPC477041
0.6685	Remote Similarity	NPC477044
0.6667	Remote Similarity	NPC474236
0.6667	Remote Similarity	NPC110158
0.6667	Remote Similarity	NPC242116
0.6647	Remote Similarity	NPC470509
0.6646	Remote Similarity	NPC85443
0.6612	Remote Similarity	NPC19692
0.6612	Remote Similarity	NPC220151
0.6607	Remote Similarity	NPC473706
0.6606	Remote Similarity	NPC251391
0.6593	Remote Similarity	NPC472113
0.6592	Remote Similarity	NPC17273
0.6592	Remote Similarity	NPC141612
0.6592	Remote Similarity	NPC476527
0.6592	Remote Similarity	NPC135601
0.6592	Remote Similarity	NPC160381
0.6591	Remote Similarity	NPC469896
0.6591	Remote Similarity	NPC79777
0.6587	Remote Similarity	NPC27296
0.6573	Remote Similarity	NPC21429
0.6564	Remote Similarity	NPC477134
0.6559	Remote Similarity	NPC477004
0.6557	Remote Similarity	NPC326422
0.6552	Remote Similarity	NPC37268
0.655	Remote Similarity	NPC114637
0.6548	Remote Similarity	NPC80681
0.6545	Remote Similarity	NPC472260
0.6543	Remote Similarity	NPC467188
0.6541	Remote Similarity	NPC141454
0.6532	Remote Similarity	NPC6982
0.6529	Remote Similarity	NPC476418
0.6529	Remote Similarity	NPC274981
0.6529	Remote Similarity	NPC8104
0.6519	Remote Similarity	NPC102338
0.6519	Remote Similarity	NPC63199
0.6519	Remote Similarity	NPC196251
0.6519	Remote Similarity	NPC111602
0.6516	Remote Similarity	NPC475450
0.6513	Remote Similarity	NPC250361
0.6508	Remote Similarity	NPC317701
0.6508	Remote Similarity	NPC165599
0.65	Remote Similarity	NPC63571
0.65	Remote Similarity	NPC279081
0.6497	Remote Similarity	NPC91179
0.6497	Remote Similarity	NPC234403
0.6489	Remote Similarity	NPC471944
0.6488	Remote Similarity	NPC299594
0.6484	Remote Similarity	NPC472112
0.6481	Remote Similarity	NPC242556
0.6478	Remote Similarity	NPC104049
0.6477	Remote Similarity	NPC145885
0.6477	Remote Similarity	NPC84827
0.6477	Remote Similarity	NPC217372
0.6477	Remote Similarity	NPC15573
0.6477	Remote Similarity	NPC183662
0.6477	Remote Similarity	NPC14113
0.6477	Remote Similarity	NPC234987
0.6474	Remote Similarity	NPC477043
0.6467	Remote Similarity	NPC209362
0.6464	Remote Similarity	NPC310633
0.6457	Remote Similarity	NPC186068
0.6452	Remote Similarity	NPC167710
0.6452	Remote Similarity	NPC22079
0.6447	Remote Similarity	NPC472285
0.6446	Remote Similarity	NPC70406
0.6446	Remote Similarity	NPC217021
0.6446	Remote Similarity	NPC470679
0.6444	Remote Similarity	NPC241025
0.6442	Remote Similarity	NPC470440
0.6441	Remote Similarity	NPC219336
0.6433	Remote Similarity	NPC306160
0.6429	Remote Similarity	NPC473762
0.6429	Remote Similarity	NPC471589
0.6429	Remote Similarity	NPC469785
0.6429	Remote Similarity	NPC221873
0.6424	Remote Similarity	NPC123906
0.6413	Remote Similarity	NPC47190
0.6409	Remote Similarity	NPC111566
0.6406	Remote Similarity	NPC244741
0.6398	Remote Similarity	NPC469768
0.6398	Remote Similarity	NPC469783
0.6398	Remote Similarity	NPC469779
0.6398	Remote Similarity	NPC469784
0.6398	Remote Similarity	NPC469767
0.6398	Remote Similarity	NPC469780
0.6398	Remote Similarity	NPC230002
0.6398	Remote Similarity	NPC469761
0.6395	Remote Similarity	NPC474383
0.6393	Remote Similarity	NPC475874
0.6393	Remote Similarity	NPC154339
0.6391	Remote Similarity	NPC213914
0.6391	Remote Similarity	NPC469762
0.6387	Remote Similarity	NPC473587
0.6387	Remote Similarity	NPC132539
0.6386	Remote Similarity	NPC105818
0.6386	Remote Similarity	NPC24678
0.6386	Remote Similarity	NPC313889
0.6384	Remote Similarity	NPC83774
0.6374	Remote Similarity	NPC473946
0.6374	Remote Similarity	NPC23476
0.6374	Remote Similarity	NPC26491
0.6374	Remote Similarity	NPC477415
0.6374	Remote Similarity	NPC474259
0.6369	Remote Similarity	NPC113626
0.6369	Remote Similarity	NPC472861
0.6369	Remote Similarity	NPC473930
0.6369	Remote Similarity	NPC75135
0.6369	Remote Similarity	NPC184932
0.6369	Remote Similarity	NPC470507

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 NPC244087 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	267
0.1-0.2	843
0.2-0.3	1560
0.3-0.4	2645
0.4-0.5	2777
0.5-0.6	950
0.6-0.7	107
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
0.7246	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD3178	Discontinued
0.6897	Remote Similarity	NPD3318	Approved
0.6897	Remote Similarity	NPD3319	Phase 1
0.6897	Remote Similarity	NPD3320	Approved
0.6857	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD1630	Approved
0.6786	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5473	Discontinued
0.6748	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD2213	Approved
0.6747	Remote Similarity	NPD2214	Approved
0.6726	Remote Similarity	NPD1631	Approved
0.6707	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD2844	Phase 3
0.6592	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.658	Remote Similarity	NPD7455	Approved
0.658	Remote Similarity	NPD7454	Approved
0.657	Remote Similarity	NPD1573	Approved
0.657	Remote Similarity	NPD1575	Approved
0.6494	Remote Similarity	NPD4524	Discontinued
0.6474	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD5787	Discontinued
0.646	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD1586	Approved
0.6448	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD4811	Discontinued
0.6413	Remote Similarity	NPD1896	Approved
0.6413	Remote Similarity	NPD4922	Phase 2
0.6404	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD3835	Phase 3
0.6386	Remote Similarity	NPD3833	Phase 3
0.6384	Remote Similarity	NPD2753	Discontinued
0.6384	Remote Similarity	NPD7865	Approved
0.6384	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5400	Approved
0.6364	Remote Similarity	NPD482	Approved
0.6358	Remote Similarity	NPD5020	Approved
0.6358	Remote Similarity	NPD1592	Phase 3
0.6348	Remote Similarity	NPD1587	Approved
0.6333	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD2095	Phase 2
0.6333	Remote Similarity	NPD2092	Phase 2
0.6333	Remote Similarity	NPD2094	Phase 2
0.6328	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD1031	Discontinued
0.631	Remote Similarity	NPD1871	Approved
0.6298	Remote Similarity	NPD2091	Phase 2
0.6298	Remote Similarity	NPD2096	Phase 2
0.6296	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD4463	Approved
0.6287	Remote Similarity	NPD4462	Approved
0.6278	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD7864	Approved
0.6264	Remote Similarity	NPD7863	Approved
0.625	Remote Similarity	NPD198	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6176	Phase 1
0.6243	Remote Similarity	NPD1745	Approved
0.6242	Remote Similarity	NPD9396	Approved
0.6242	Remote Similarity	NPD9392	Approved
0.6236	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD4804	Approved
0.6235	Remote Similarity	NPD786	Approved
0.6229	Remote Similarity	NPD1343	Approved
0.6229	Remote Similarity	NPD7866	Approved
0.6223	Remote Similarity	NPD4848	Phase 1
0.6218	Remote Similarity	NPD5901	Discontinued
0.6218	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4499	Approved
0.6211	Remote Similarity	NPD201	Phase 2
0.6211	Remote Similarity	NPD200	Phase 2
0.6211	Remote Similarity	NPD1262	Discovery
0.6209	Remote Similarity	NPD7564	Discontinued
0.6209	Remote Similarity	NPD1096	Discontinued
0.6203	Remote Similarity	NPD460	Discontinued
0.6196	Remote Similarity	NPD3246	Discontinued
0.6186	Remote Similarity	NPD2008	Discontinued
0.6186	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5254	Discontinued
0.6178	Remote Similarity	NPD4501	Approved
0.6178	Remote Similarity	NPD4500	Approved
0.6173	Remote Similarity	NPD4506	Discontinued
0.617	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD3077	Approved
0.6167	Remote Similarity	NPD3079	Approved
0.6167	Remote Similarity	NPD3078	Approved
0.6167	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD3076	Approved
0.6164	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD4805	Approved
0.6159	Remote Similarity	NPD1722	Approved
0.615	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD7727	Phase 2
0.6146	Remote Similarity	NPD7817	Phase 1
0.6142	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD5809	Phase 3
0.614	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD680	Discontinued
0.6134	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD3947	Discontinued
0.6133	Remote Similarity	NPD1643	Phase 3
0.6129	Remote Similarity	NPD5685	Approved
0.6129	Remote Similarity	NPD5686	Approved
0.6122	Remote Similarity	NPD6376	Discontinued
0.6122	Remote Similarity	NPD2509	Approved
0.6122	Remote Similarity	NPD2510	Approved
0.6118	Remote Similarity	NPD1079	Discontinued
0.6117	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD9599	Approved
0.6092	Remote Similarity	NPD6771	Discontinued
0.6091	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD1600	Suspended
0.6089	Remote Similarity	NPD4883	Approved
0.6087	Remote Similarity	NPD272	Approved
0.6085	Remote Similarity	NPD7619	Phase 3
0.6085	Remote Similarity	NPD7618	Phase 3
0.6073	Remote Similarity	NPD1982	Phase 1
0.6071	Remote Similarity	NPD1270	Approved
0.607	Remote Similarity	NPD3394	Approved
0.607	Remote Similarity	NPD3393	Approved
0.607	Remote Similarity	NPD3389	Approved
0.6059	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD5199	Approved
0.6059	Remote Similarity	NPD5198	Approved
0.6057	Remote Similarity	NPD3583	Phase 2
0.6054	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD56	Approved
0.6051	Remote Similarity	NPD8098	Approved
0.6051	Remote Similarity	NPD8282	Approved
0.6051	Remote Similarity	NPD8114	Approved
0.6051	Remote Similarity	NPD8115	Approved
0.6051	Remote Similarity	NPD8283	Approved
0.6045	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD2481	Approved
0.6044	Remote Similarity	NPD3927	Phase 2
0.6044	Remote Similarity	NPD2479	Phase 3
0.6043	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6041	Remote Similarity	NPD8399	Phase 1
0.6041	Remote Similarity	NPD8423	Phase 2
0.6036	Remote Similarity	NPD3100	Discontinued
0.6036	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD750	Phase 2
0.6029	Remote Similarity	NPD5479	Discontinued
0.6023	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD2915	Discontinued
0.6022	Remote Similarity	NPD4988	Discontinued
0.6021	Remote Similarity	NPD6664	Approved
0.602	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.601	Remote Similarity	NPD4601	Approved
0.601	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.601	Remote Similarity	NPD4600	Approved
0.601	Remote Similarity	NPD7941	Phase 3
0.6	Remote Similarity	NPD2411	Approved
0.6	Remote Similarity	NPD2172	Phase 1
0.6	Remote Similarity	NPD5853	Phase 3
0.6	Remote Similarity	NPD5855	Phase 3
0.6	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8097	Phase 3
0.6	Remote Similarity	NPD8096	Phase 3
0.5989	Remote Similarity	NPD1534	Approved
0.5988	Remote Similarity	NPD4880	Discontinued
0.5988	Remote Similarity	NPD2061	Approved
0.598	Remote Similarity	NPD6770	Approved
0.5979	Remote Similarity	NPD5017	Discontinued
0.5978	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.5975	Remote Similarity	NPD1619	Phase 3
0.5975	Remote Similarity	NPD3654	Approved
0.5969	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.5967	Remote Similarity	NPD3238	Discontinued
0.5967	Remote Similarity	NPD4075	Phase 2
0.5964	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD9100	Approved
0.596	Remote Similarity	NPD2442	Approved
0.596	Remote Similarity	NPD2443	Approved
0.596	Remote Similarity	NPD6459	Phase 2
0.5952	Remote Similarity	NPD175	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD6579	Phase 2
0.5944	Remote Similarity	NPD3868	Phase 1
0.5943	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD2880	Discontinued
0.5938	Remote Similarity	NPD3476	Approved
0.5938	Remote Similarity	NPD3475	Approved
0.5936	Remote Similarity	NPD4948	Discontinued
0.593	Remote Similarity	NPD2837	Discontinued
0.5928	Remote Similarity	NPD9724	Phase 1
0.5928	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD1658	Discontinued
0.592	Remote Similarity	NPD7656	Approved
0.592	Remote Similarity	NPD7657	Approved
0.5916	Remote Similarity	NPD7406	Phase 2
0.5912	Remote Similarity	NPD2918	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