NPASS Compound

Structure

NPC114033 OpenBabel07101719522D 23 23 0 0 0 0 0 0 0 0999 V2000 12.1208 0.5727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9397 -1.1498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3347 2.9225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3292 2.8180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7469 2.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7360 1.9044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7524 2.2180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7305 1.7999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1646 1.4090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1372 0.8863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1701 1.5135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1317 0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5823 0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5385 -0.1317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.8090 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 0.5000 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5330 -0.2363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 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 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4680 -2.2382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 4 2 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 19 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 21 1 0 0 0 0 18 23 2 0 0 0 0 20 22 1 0 0 0 0 21 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	317.27
Volume:	372.457
LogP:	6.906
LogD:	4.866
LogS:	-3.236
# Rotatable Bonds:	14
TPSA:	32.86
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.238
Synthetic Accessibility Score:	2.713
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.855
MDCK Permeability:	2.2365218683262356e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.926
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.544
Plasma Protein Binding (PPB):	98.5296859741211%
Volume Distribution (VD):	4.472
Pgp-substrate:	0.9291855692863464%

ADMET: Metabolism

CYP1A2-inhibitor:	0.388
CYP1A2-substrate:	0.215
CYP2C19-inhibitor:	0.619
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.57
CYP2C9-substrate:	0.982
CYP2D6-inhibitor:	0.456
CYP2D6-substrate:	0.415
CYP3A4-inhibitor:	0.605
CYP3A4-substrate:	0.119

ADMET: Excretion

Clearance (CL):	3.729
Half-life (T1/2):	0.643

ADMET: Toxicity

hERG Blockers:	0.253
Human Hepatotoxicity (H-HT):	0.114
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.139
Skin Sensitization:	0.947
Carcinogencity:	0.09
Eye Corrosion:	0.531
Eye Irritation:	0.966
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC114033

Natural Product ID:	NPC114033
*Common Name:**	Mycalazal 17
IUPAC Name:	5-[(Z)-14-methylpentadec-7-enyl]-1H-pyrrole-2-carbaldehyde
Synonyms:	Mycalazal 17
Standard InCHIKey:	LFQGTEBVKFINCF-ARJAWSKDSA-N
Standard InCHI:	InChI=1S/C21H35NO/c1-19(2)14-12-10-8-6-4-3-5-7-9-11-13-15-20-16-17-21(18-23)22-20/h3-4,16-19,22H,5-15H2,1-2H3/b4-3-
SMILES:	O=Cc1ccc([nH]1)CCCCCC/C=CCCCCCC(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1080442
PubChem CID:	44605147
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	=	20000.0	nM	PMID[556082]

☑ 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 NPC114033 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	354
0.1-0.2	4293
0.2-0.3	19685
0.3-0.4	12646
0.4-0.5	2757
0.5-0.6	2056
0.6-0.7	808
0.7-0.8	68
0.8-0.85	4
0.85-0.9	0
0.9-0.95	14
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC101130
1.0	High Similarity	NPC129412
1.0	High Similarity	NPC58268
0.9624	High Similarity	NPC200397
0.9624	High Similarity	NPC195704
0.9624	High Similarity	NPC167200
0.9624	High Similarity	NPC98156
0.9624	High Similarity	NPC138596
0.9624	High Similarity	NPC292434
0.9624	High Similarity	NPC14448
0.9624	High Similarity	NPC64661
0.9203	High Similarity	NPC48171
0.9203	High Similarity	NPC205604
0.9203	High Similarity	NPC74928
0.9203	High Similarity	NPC77582
0.9203	High Similarity	NPC129753
0.9203	High Similarity	NPC97230
0.9203	High Similarity	NPC12831
0.9203	High Similarity	NPC169308
0.9203	High Similarity	NPC244087
0.9203	High Similarity	NPC209281
0.9203	High Similarity	NPC3698
0.9203	High Similarity	NPC59839
0.9203	High Similarity	NPC302717
0.9203	High Similarity	NPC286529
0.817	Intermediate Similarity	NPC76982
0.8056	Intermediate Similarity	NPC23215
0.7911	Intermediate Similarity	NPC115232
0.7808	Intermediate Similarity	NPC291517
0.7778	Intermediate Similarity	NPC13432
0.7688	Intermediate Similarity	NPC71132
0.7651	Intermediate Similarity	NPC477042
0.7586	Intermediate Similarity	NPC71236
0.7584	Intermediate Similarity	NPC472288
0.7578	Intermediate Similarity	NPC42372
0.7576	Intermediate Similarity	NPC151635
0.7562	Intermediate Similarity	NPC214106
0.7561	Intermediate Similarity	NPC252572
0.7551	Intermediate Similarity	NPC20021
0.7515	Intermediate Similarity	NPC293216
0.7471	Intermediate Similarity	NPC133003
0.7458	Intermediate Similarity	NPC472297
0.7458	Intermediate Similarity	NPC472296
0.7383	Intermediate Similarity	NPC150592
0.736	Intermediate Similarity	NPC477045
0.7353	Intermediate Similarity	NPC102755
0.7337	Intermediate Similarity	NPC88110
0.7333	Intermediate Similarity	NPC471943
0.7314	Intermediate Similarity	NPC472292
0.731	Intermediate Similarity	NPC477003
0.7301	Intermediate Similarity	NPC21174
0.7301	Intermediate Similarity	NPC271797
0.7299	Intermediate Similarity	NPC324091
0.7294	Intermediate Similarity	NPC470677
0.7288	Intermediate Similarity	NPC472293
0.7279	Intermediate Similarity	NPC313823
0.7278	Intermediate Similarity	NPC471655
0.7273	Intermediate Similarity	NPC81802
0.7273	Intermediate Similarity	NPC269886
0.7273	Intermediate Similarity	NPC247735
0.7273	Intermediate Similarity	NPC472210
0.7273	Intermediate Similarity	NPC472295
0.7251	Intermediate Similarity	NPC159125
0.7244	Intermediate Similarity	NPC260041
0.7241	Intermediate Similarity	NPC209917
0.7222	Intermediate Similarity	NPC474492
0.7219	Intermediate Similarity	NPC284775
0.7207	Intermediate Similarity	NPC477041
0.7207	Intermediate Similarity	NPC477044
0.7178	Intermediate Similarity	NPC100104
0.7178	Intermediate Similarity	NPC470680
0.7152	Intermediate Similarity	NPC233380
0.7151	Intermediate Similarity	NPC117027
0.7143	Intermediate Similarity	NPC161861
0.7134	Intermediate Similarity	NPC242116
0.7103	Intermediate Similarity	NPC41174
0.7095	Intermediate Similarity	NPC79356
0.7095	Intermediate Similarity	NPC102592
0.7093	Intermediate Similarity	NPC191415
0.7083	Intermediate Similarity	NPC262338
0.7063	Intermediate Similarity	NPC473878
0.7062	Intermediate Similarity	NPC476460
0.7045	Intermediate Similarity	NPC473666
0.7044	Intermediate Similarity	NPC100726
0.7039	Intermediate Similarity	NPC19692
0.7039	Intermediate Similarity	NPC220151
0.7029	Intermediate Similarity	NPC160381
0.7022	Intermediate Similarity	NPC472113
0.702	Intermediate Similarity	NPC475450
0.7012	Intermediate Similarity	NPC80681
0.7011	Intermediate Similarity	NPC110158
0.7006	Intermediate Similarity	NPC470509
0.7006	Intermediate Similarity	NPC114637
0.6983	Remote Similarity	NPC304203
0.6982	Remote Similarity	NPC6982
0.6973	Remote Similarity	NPC477043
0.6954	Remote Similarity	NPC475428
0.6954	Remote Similarity	NPC470205
0.6949	Remote Similarity	NPC102338
0.6949	Remote Similarity	NPC196251
0.6949	Remote Similarity	NPC63199
0.6949	Remote Similarity	NPC111602
0.6946	Remote Similarity	NPC2414
0.6936	Remote Similarity	NPC469896
0.6932	Remote Similarity	NPC135601
0.6932	Remote Similarity	NPC141612
0.6932	Remote Similarity	NPC17273
0.6919	Remote Similarity	NPC234987
0.6913	Remote Similarity	NPC250361
0.691	Remote Similarity	NPC472112
0.6887	Remote Similarity	NPC473587
0.6871	Remote Similarity	NPC251391
0.6868	Remote Similarity	NPC141454
0.6855	Remote Similarity	NPC242556
0.6848	Remote Similarity	NPC299594
0.6842	Remote Similarity	NPC22079
0.6839	Remote Similarity	NPC79777
0.6839	Remote Similarity	NPC91179
0.6836	Remote Similarity	NPC476527
0.6833	Remote Similarity	NPC47190
0.6829	Remote Similarity	NPC33229
0.6828	Remote Similarity	NPC165599
0.6828	Remote Similarity	NPC317701
0.6821	Remote Similarity	NPC14113
0.6821	Remote Similarity	NPC83774
0.6821	Remote Similarity	NPC473762
0.6821	Remote Similarity	NPC84827
0.6821	Remote Similarity	NPC145885
0.6818	Remote Similarity	NPC21429
0.6813	Remote Similarity	NPC470440
0.6813	Remote Similarity	NPC467188
0.681	Remote Similarity	NPC470679
0.681	Remote Similarity	NPC217021
0.68	Remote Similarity	NPC113626
0.6797	Remote Similarity	NPC179365
0.6796	Remote Similarity	NPC326422
0.6796	Remote Similarity	NPC267343
0.6793	Remote Similarity	NPC477004
0.6788	Remote Similarity	NPC142688
0.6786	Remote Similarity	NPC206148
0.6786	Remote Similarity	NPC274981
0.6786	Remote Similarity	NPC8104
0.6782	Remote Similarity	NPC219336
0.6772	Remote Similarity	NPC469780
0.6772	Remote Similarity	NPC469783
0.6772	Remote Similarity	NPC59084
0.6772	Remote Similarity	NPC469761
0.6772	Remote Similarity	NPC469779
0.6772	Remote Similarity	NPC469768
0.6772	Remote Similarity	NPC469767
0.6772	Remote Similarity	NPC469784
0.6765	Remote Similarity	NPC70949
0.676	Remote Similarity	NPC175474
0.6753	Remote Similarity	NPC473930
0.6752	Remote Similarity	NPC104049
0.6748	Remote Similarity	NPC24678
0.6748	Remote Similarity	NPC105818
0.6743	Remote Similarity	NPC234403
0.6743	Remote Similarity	NPC61011
0.6739	Remote Similarity	NPC195457
0.673	Remote Similarity	NPC63157
0.673	Remote Similarity	NPC473868
0.673	Remote Similarity	NPC469766
0.6727	Remote Similarity	NPC470507
0.6727	Remote Similarity	NPC209362
0.6724	Remote Similarity	NPC15573
0.6724	Remote Similarity	NPC183662
0.6724	Remote Similarity	NPC217372
0.6723	Remote Similarity	NPC228835
0.6722	Remote Similarity	NPC154339
0.672	Remote Similarity	NPC471944
0.6711	Remote Similarity	NPC471589
0.6708	Remote Similarity	NPC314372
0.6707	Remote Similarity	NPC472260
0.6707	Remote Similarity	NPC70406
0.6706	Remote Similarity	NPC326479
0.6705	Remote Similarity	NPC37268
0.6705	Remote Similarity	NPC186068
0.6703	Remote Similarity	NPC237414
0.6702	Remote Similarity	NPC132539
0.6702	Remote Similarity	NPC303951
0.6687	Remote Similarity	NPC37548
0.6687	Remote Similarity	NPC469785
0.6687	Remote Similarity	NPC190296
0.6687	Remote Similarity	NPC123906
0.6687	Remote Similarity	NPC124005
0.6686	Remote Similarity	NPC54214
0.6686	Remote Similarity	NPC271734
0.6686	Remote Similarity	NPC11126
0.6686	Remote Similarity	NPC126709
0.6686	Remote Similarity	NPC213468
0.6686	Remote Similarity	NPC248041
0.6685	Remote Similarity	NPC241025
0.6685	Remote Similarity	NPC138370
0.6685	Remote Similarity	NPC167710
0.6684	Remote Similarity	NPC472291
0.6667	Remote Similarity	NPC469765
0.6667	Remote Similarity	NPC2949
0.6667	Remote Similarity	NPC221873
0.6667	Remote Similarity	NPC78020

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 NPC114033 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	713
0.2-0.3	1247
0.3-0.4	2531
0.4-0.5	2854
0.5-0.6	1336
0.6-0.7	209
0.7-0.8	15
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
0.7622	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD3178	Discontinued
0.7368	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1630	Approved
0.7251	Intermediate Similarity	NPD3319	Phase 1
0.7251	Intermediate Similarity	NPD3318	Approved
0.7251	Intermediate Similarity	NPD3320	Approved
0.7222	Intermediate Similarity	NPD2214	Approved
0.7222	Intermediate Similarity	NPD2213	Approved
0.7209	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD1631	Approved
0.7135	Intermediate Similarity	NPD5473	Discontinued
0.7108	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD1573	Approved
0.7024	Intermediate Similarity	NPD1575	Approved
0.6901	Remote Similarity	NPD1586	Approved
0.6864	Remote Similarity	NPD2844	Phase 3
0.6845	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4524	Discontinued
0.6821	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD1587	Approved
0.6768	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.674	Remote Similarity	NPD1896	Approved
0.673	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5020	Approved
0.6724	Remote Similarity	NPD7865	Approved
0.6702	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1343	Approved
0.6667	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4463	Approved
0.6646	Remote Similarity	NPD3833	Phase 3
0.6646	Remote Similarity	NPD4462	Approved
0.6646	Remote Similarity	NPD3835	Phase 3
0.6645	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4499	Approved
0.663	Remote Similarity	NPD1871	Approved
0.6625	Remote Similarity	NPD1592	Phase 3
0.6609	Remote Similarity	NPD482	Approved
0.6608	Remote Similarity	NPD7864	Approved
0.6608	Remote Similarity	NPD7863	Approved
0.6606	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD786	Approved
0.6578	Remote Similarity	NPD4501	Approved
0.6578	Remote Similarity	NPD4500	Approved
0.6573	Remote Similarity	NPD2094	Phase 2
0.6573	Remote Similarity	NPD2092	Phase 2
0.6573	Remote Similarity	NPD2095	Phase 2
0.6571	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7866	Approved
0.6562	Remote Similarity	NPD4506	Discontinued
0.6561	Remote Similarity	NPD6176	Phase 1
0.6546	Remote Similarity	NPD7454	Approved
0.6546	Remote Similarity	NPD7455	Approved
0.6543	Remote Similarity	NPD5254	Discontinued
0.6536	Remote Similarity	NPD2091	Phase 2
0.6536	Remote Similarity	NPD7564	Discontinued
0.6536	Remote Similarity	NPD2096	Phase 2
0.6522	Remote Similarity	NPD460	Discontinued
0.6522	Remote Similarity	NPD1722	Approved
0.6519	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.651	Remote Similarity	NPD6376	Discontinued
0.6492	Remote Similarity	NPD2008	Discontinued
0.6492	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD1534	Approved
0.6478	Remote Similarity	NPD1262	Discovery
0.6478	Remote Similarity	NPD200	Phase 2
0.6478	Remote Similarity	NPD201	Phase 2
0.6474	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD4880	Discontinued
0.6455	Remote Similarity	NPD7817	Phase 1
0.6453	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4848	Phase 1
0.6444	Remote Similarity	NPD1096	Discontinued
0.6443	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.644	Remote Similarity	NPD8282	Approved
0.644	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.644	Remote Similarity	NPD56	Approved
0.644	Remote Similarity	NPD8098	Approved
0.644	Remote Similarity	NPD8283	Approved
0.644	Remote Similarity	NPD5901	Discontinued
0.6432	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD8423	Phase 2
0.6425	Remote Similarity	NPD8399	Phase 1
0.6425	Remote Similarity	NPD2510	Approved
0.6425	Remote Similarity	NPD2509	Approved
0.6424	Remote Similarity	NPD1270	Approved
0.6424	Remote Similarity	NPD5787	Discontinued
0.6417	Remote Similarity	NPD6664	Approved
0.6413	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD3076	Approved
0.6404	Remote Similarity	NPD3079	Approved
0.6404	Remote Similarity	NPD3078	Approved
0.6404	Remote Similarity	NPD3077	Approved
0.6402	Remote Similarity	NPD4601	Approved
0.6402	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD4600	Approved
0.64	Remote Similarity	NPD1079	Discontinued
0.6398	Remote Similarity	NPD7619	Phase 3
0.6398	Remote Similarity	NPD7618	Phase 3
0.6395	Remote Similarity	NPD3583	Phase 2
0.6392	Remote Similarity	NPD7941	Phase 3
0.6392	Remote Similarity	NPD1600	Suspended
0.6389	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD3100	Discontinued
0.6384	Remote Similarity	NPD4075	Phase 2
0.6384	Remote Similarity	NPD3238	Discontinued
0.6383	Remote Similarity	NPD1982	Phase 1
0.6378	Remote Similarity	NPD8097	Phase 3
0.6378	Remote Similarity	NPD2411	Approved
0.6378	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD8096	Phase 3
0.6374	Remote Similarity	NPD5809	Phase 3
0.6374	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD1643	Phase 3
0.6368	Remote Similarity	NPD7727	Phase 2
0.6364	Remote Similarity	NPD750	Phase 2
0.6364	Remote Similarity	NPD3389	Approved
0.6364	Remote Similarity	NPD3394	Approved
0.6364	Remote Similarity	NPD3393	Approved
0.6358	Remote Similarity	NPD2915	Discontinued
0.6354	Remote Similarity	NPD8115	Approved
0.6354	Remote Similarity	NPD3947	Discontinued
0.6354	Remote Similarity	NPD8114	Approved
0.6352	Remote Similarity	NPD272	Approved
0.635	Remote Similarity	NPD6770	Approved
0.6348	Remote Similarity	NPD2753	Discontinued
0.6347	Remote Similarity	NPD2172	Phase 1
0.6346	Remote Similarity	NPD3654	Approved
0.6339	Remote Similarity	NPD3246	Discontinued
0.6339	Remote Similarity	NPD4988	Discontinued
0.633	Remote Similarity	NPD2880	Discontinued
0.633	Remote Similarity	NPD5003	Discontinued
0.631	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD3475	Approved
0.6306	Remote Similarity	NPD3476	Approved
0.6298	Remote Similarity	NPD1745	Approved
0.6294	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD4811	Discontinued
0.629	Remote Similarity	NPD4922	Phase 2
0.6287	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD3315	Phase 3
0.6282	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD1031	Discontinued
0.6281	Remote Similarity	NPD8160	Phase 2
0.628	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.628	Remote Similarity	NPD3717	Discontinued
0.6278	Remote Similarity	NPD2481	Approved
0.6278	Remote Similarity	NPD2479	Phase 3
0.6278	Remote Similarity	NPD3927	Phase 2
0.6275	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.627	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5199	Approved
0.6269	Remote Similarity	NPD5198	Approved
0.6264	Remote Similarity	NPD7482	Phase 2
0.6264	Remote Similarity	NPD7483	Phase 2
0.6258	Remote Similarity	NPD9599	Approved
0.6257	Remote Similarity	NPD3506	Approved
0.6257	Remote Similarity	NPD7869	Discontinued
0.6257	Remote Similarity	NPD3505	Approved
0.6256	Remote Similarity	NPD2442	Approved
0.6256	Remote Similarity	NPD2443	Approved
0.625	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD1619	Phase 3
0.6236	Remote Similarity	NPD4883	Approved
0.6235	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD5479	Discontinued
0.6231	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD7406	Phase 2
0.6222	Remote Similarity	NPD4079	Approved
0.6222	Remote Similarity	NPD4076	Approved
0.6218	Remote Similarity	NPD2119	Approved
0.6218	Remote Similarity	NPD2118	Approved
0.6213	Remote Similarity	NPD7882	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD7657	Approved
0.6212	Remote Similarity	NPD7656	Approved
0.6211	Remote Similarity	NPD7946	Pre-registration
0.6205	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD5104	Approved
0.62	Remote Similarity	NPD9396	Approved
0.62	Remote Similarity	NPD9392	Approved
0.6198	Remote Similarity	NPD5017	Discontinued
0.6196	Remote Similarity	NPD4804	Approved
0.6193	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.619	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD5146	Suspended
0.6188	Remote Similarity	NPD3385	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