NPASS Compound

Structure

NPC195704 OpenBabel07101719252D 26 26 0 0 0 0 0 0 0 0999 V2000 1.6750 -9.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -9.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -10.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 -11.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5411 -10.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4071 -11.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2731 -10.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2731 -9.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1391 -9.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1391 -8.0878 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 4.2731 -6.5878 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 -5.0878 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 -3.5878 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 -2.0878 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 -0.2788 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 0.0000 -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 2 3 1 0 0 0 0 3 4 2 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 2 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 23 2 0 0 0 0 21 24 2 0 0 0 0 22 24 1 0 0 0 0 22 26 2 0 0 0 0 23 25 1 0 0 0 0 24 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	355.29
Volume:	419.072
LogP:	5.552
LogD:	4.59
LogS:	-2.772
# Rotatable Bonds:	16
TPSA:	32.86
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.188
Synthetic Accessibility Score:	3.046
Fsp3:	0.542
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:	-5.042
MDCK Permeability:	6.082183608668856e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.178
Plasma Protein Binding (PPB):	99.55243682861328%
Volume Distribution (VD):	4.519
Pgp-substrate:	0.5794357061386108%

ADMET: Metabolism

CYP1A2-inhibitor:	0.448
CYP1A2-substrate:	0.591
CYP2C19-inhibitor:	0.681
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.603
CYP2C9-substrate:	0.978
CYP2D6-inhibitor:	0.755
CYP2D6-substrate:	0.923
CYP3A4-inhibitor:	0.855
CYP3A4-substrate:	0.116

ADMET: Excretion

Clearance (CL):	3.443
Half-life (T1/2):	0.902

ADMET: Toxicity

hERG Blockers:	0.258
Human Hepatotoxicity (H-HT):	0.229
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.863
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.547
Skin Sensitization:	0.962
Carcinogencity:	0.635
Eye Corrosion:	0.096
Eye Irritation:	0.604
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC195704

Natural Product ID:	NPC195704
*Common Name:**	Mycalazal 20
IUPAC Name:	5-[(10Z,13Z,16Z)-nonadeca-10,13,16-trienyl]-1H-pyrrole-2-carbaldehyde
Synonyms:	Mycalazal 20
Standard InCHIKey:	VEOUIFWXVMDSPJ-PDBXOOCHSA-N
Standard InCHI:	InChI=1S/C24H37NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23-20-21-24(22-26)25-23/h3-4,6-7,9-10,20-22,25H,2,5,8,11-19H2,1H3/b4-3-,7-6-,10-9-
SMILES:	CC/C=CC/C=CC/C=CCCCCCCCCCc1ccc([nH]1)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079378
PubChem CID:	44605150
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[525570]

☑ 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 NPC195704 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	374
0.1-0.2	7539
0.2-0.3	21052
0.3-0.4	8595
0.4-0.5	2650
0.5-0.6	1841
0.6-0.7	570
0.7-0.8	46
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC167200
1.0	High Similarity	NPC64661
1.0	High Similarity	NPC200397
1.0	High Similarity	NPC98156
1.0	High Similarity	NPC292434
1.0	High Similarity	NPC14448
1.0	High Similarity	NPC138596
0.9624	High Similarity	NPC58268
0.9624	High Similarity	NPC129412
0.9624	High Similarity	NPC101130
0.9624	High Similarity	NPC114033
0.9549	High Similarity	NPC205604
0.9549	High Similarity	NPC77582
0.9549	High Similarity	NPC286529
0.9549	High Similarity	NPC12831
0.9549	High Similarity	NPC129753
0.9549	High Similarity	NPC169308
0.9549	High Similarity	NPC48171
0.9549	High Similarity	NPC59839
0.9549	High Similarity	NPC209281
0.9549	High Similarity	NPC244087
0.9549	High Similarity	NPC74928
0.9549	High Similarity	NPC302717
0.9549	High Similarity	NPC97230
0.9549	High Similarity	NPC3698
0.8345	Intermediate Similarity	NPC23215
0.8085	Intermediate Similarity	NPC291517
0.8041	Intermediate Similarity	NPC13432
0.7961	Intermediate Similarity	NPC76982
0.7857	Intermediate Similarity	NPC71236
0.7847	Intermediate Similarity	NPC472288
0.7817	Intermediate Similarity	NPC20021
0.7707	Intermediate Similarity	NPC115232
0.7639	Intermediate Similarity	NPC150592
0.7535	Intermediate Similarity	NPC313823
0.7483	Intermediate Similarity	NPC260041
0.7378	Intermediate Similarity	NPC151635
0.7375	Intermediate Similarity	NPC42372
0.7375	Intermediate Similarity	NPC71132
0.7362	Intermediate Similarity	NPC252572
0.7358	Intermediate Similarity	NPC214106
0.7349	Intermediate Similarity	NPC477042
0.7317	Intermediate Similarity	NPC293216
0.7278	Intermediate Similarity	NPC133003
0.7239	Intermediate Similarity	NPC471943
0.7179	Intermediate Similarity	NPC471655
0.7175	Intermediate Similarity	NPC472297
0.7175	Intermediate Similarity	NPC472296
0.716	Intermediate Similarity	NPC102755
0.7143	Intermediate Similarity	NPC88110
0.7118	Intermediate Similarity	NPC477003
0.711	Intermediate Similarity	NPC324091
0.7101	Intermediate Similarity	NPC470677
0.7079	Intermediate Similarity	NPC477045
0.7059	Intermediate Similarity	NPC159125
0.7055	Intermediate Similarity	NPC233380
0.7052	Intermediate Similarity	NPC209917
0.7044	Intermediate Similarity	NPC33229
0.7029	Intermediate Similarity	NPC472292
0.7024	Intermediate Similarity	NPC284775
0.7019	Intermediate Similarity	NPC474492
0.7006	Intermediate Similarity	NPC472293
0.7	Intermediate Similarity	NPC142688
0.6994	Remote Similarity	NPC271797
0.6994	Remote Similarity	NPC206148
0.6994	Remote Similarity	NPC21174
0.6993	Remote Similarity	NPC41174
0.6989	Remote Similarity	NPC81802
0.6989	Remote Similarity	NPC247735
0.6989	Remote Similarity	NPC472295
0.6989	Remote Similarity	NPC269886
0.6989	Remote Similarity	NPC472210
0.6975	Remote Similarity	NPC100104
0.6975	Remote Similarity	NPC470680
0.6959	Remote Similarity	NPC117027
0.6946	Remote Similarity	NPC161861
0.6943	Remote Similarity	NPC100726
0.6933	Remote Similarity	NPC242116
0.6927	Remote Similarity	NPC477041
0.6927	Remote Similarity	NPC477044
0.691	Remote Similarity	NPC102592
0.691	Remote Similarity	NPC79356
0.6901	Remote Similarity	NPC191415
0.6886	Remote Similarity	NPC54214
0.6886	Remote Similarity	NPC262338
0.6875	Remote Similarity	NPC476460
0.6857	Remote Similarity	NPC473666
0.6855	Remote Similarity	NPC52110
0.6855	Remote Similarity	NPC473878
0.6848	Remote Similarity	NPC2414
0.6839	Remote Similarity	NPC160381
0.6821	Remote Similarity	NPC110158
0.6818	Remote Similarity	NPC85443
0.681	Remote Similarity	NPC80681
0.6807	Remote Similarity	NPC470509
0.6807	Remote Similarity	NPC114637
0.68	Remote Similarity	NPC475450
0.6798	Remote Similarity	NPC304203
0.677	Remote Similarity	NPC251391
0.6763	Remote Similarity	NPC470205
0.676	Remote Similarity	NPC220151
0.676	Remote Similarity	NPC19692
0.6748	Remote Similarity	NPC27296
0.6746	Remote Similarity	NPC80528
0.6744	Remote Similarity	NPC469896
0.6743	Remote Similarity	NPC141612
0.6743	Remote Similarity	NPC17273
0.6743	Remote Similarity	NPC135601
0.6742	Remote Similarity	NPC472113
0.6728	Remote Similarity	NPC474236
0.6709	Remote Similarity	NPC467188
0.6708	Remote Similarity	NPC472260
0.6703	Remote Similarity	NPC477043
0.6689	Remote Similarity	NPC250361
0.6687	Remote Similarity	NPC8104
0.6687	Remote Similarity	NPC476418
0.6686	Remote Similarity	NPC6982
0.6685	Remote Similarity	NPC141454
0.6667	Remote Similarity	NPC473587
0.6667	Remote Similarity	NPC196251
0.6667	Remote Similarity	NPC111602
0.6667	Remote Similarity	NPC473706
0.6667	Remote Similarity	NPC63199
0.6667	Remote Similarity	NPC213774
0.6667	Remote Similarity	NPC102338
0.6649	Remote Similarity	NPC317701
0.6649	Remote Similarity	NPC165599
0.6648	Remote Similarity	NPC476527
0.6647	Remote Similarity	NPC91179
0.6647	Remote Similarity	NPC79777
0.6646	Remote Similarity	NPC242556
0.6646	Remote Similarity	NPC299594
0.6645	Remote Similarity	NPC104049
0.6629	Remote Similarity	NPC472112
0.6629	Remote Similarity	NPC21429
0.6628	Remote Similarity	NPC84827
0.6628	Remote Similarity	NPC234987
0.6628	Remote Similarity	NPC145885
0.6628	Remote Similarity	NPC14113
0.6626	Remote Similarity	NPC75135
0.6626	Remote Similarity	NPC209362
0.6623	Remote Similarity	NPC475428
0.6623	Remote Similarity	NPC22079
0.6612	Remote Similarity	NPC477004
0.6611	Remote Similarity	NPC326422
0.6608	Remote Similarity	NPC37268
0.6605	Remote Similarity	NPC470679
0.6605	Remote Similarity	NPC217021
0.6605	Remote Similarity	NPC70406
0.6604	Remote Similarity	NPC470440
0.66	Remote Similarity	NPC473762
0.66	Remote Similarity	NPC471589
0.6591	Remote Similarity	NPC241025
0.659	Remote Similarity	NPC219336
0.6587	Remote Similarity	NPC306160
0.6587	Remote Similarity	NPC274981
0.6585	Remote Similarity	NPC169586
0.6584	Remote Similarity	NPC123906
0.6579	Remote Similarity	NPC179365
0.6568	Remote Similarity	NPC70949
0.6561	Remote Similarity	NPC469784
0.6561	Remote Similarity	NPC469761
0.6561	Remote Similarity	NPC469768
0.6561	Remote Similarity	NPC469767
0.6561	Remote Similarity	NPC469780
0.6561	Remote Similarity	NPC469783
0.6561	Remote Similarity	NPC469779
0.6556	Remote Similarity	NPC47190
0.6554	Remote Similarity	NPC63571
0.6552	Remote Similarity	NPC234403
0.6543	Remote Similarity	NPC313889
0.6543	Remote Similarity	NPC105818
0.6543	Remote Similarity	NPC24678
0.6541	Remote Similarity	NPC471944
0.6536	Remote Similarity	NPC473930
0.6536	Remote Similarity	NPC154339
0.6532	Remote Similarity	NPC15573
0.6532	Remote Similarity	NPC217372
0.6532	Remote Similarity	NPC183662
0.6532	Remote Similarity	NPC83774
0.6527	Remote Similarity	NPC26491
0.6526	Remote Similarity	NPC303951
0.6524	Remote Similarity	NPC470507
0.6524	Remote Similarity	NPC132539
0.6522	Remote Similarity	NPC105811
0.6519	Remote Similarity	NPC469766
0.6519	Remote Similarity	NPC267343
0.6517	Remote Similarity	NPC310633
0.6514	Remote Similarity	NPC113626
0.6512	Remote Similarity	NPC186068
0.6503	Remote Similarity	NPC167710
0.65	Remote Similarity	NPC138370
0.65	Remote Similarity	NPC314372
0.6495	Remote Similarity	NPC472285
0.6494	Remote Similarity	NPC248041
0.6494	Remote Similarity	NPC126709
0.6494	Remote Similarity	NPC11126
0.6492	Remote Similarity	NPC9894
0.6492	Remote Similarity	NPC23294
0.6489	Remote Similarity	NPC45190

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 NPC195704 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	237
0.1-0.2	830
0.2-0.3	1456
0.3-0.4	2616
0.4-0.5	2786
0.5-0.6	1079
0.6-0.7	143
0.7-0.8	3
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
0.7423	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3178	Discontinued
0.7125	Intermediate Similarity	NPD1630	Approved
0.7059	Intermediate Similarity	NPD3318	Approved
0.7059	Intermediate Similarity	NPD3319	Phase 1
0.7059	Intermediate Similarity	NPD3320	Approved
0.7018	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1631	Approved
0.6981	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2213	Approved
0.6914	Remote Similarity	NPD2214	Approved
0.6842	Remote Similarity	NPD5473	Discontinued
0.6813	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2844	Phase 3
0.6743	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD1573	Approved
0.6726	Remote Similarity	NPD1575	Approved
0.6706	Remote Similarity	NPD1586	Approved
0.6647	Remote Similarity	NPD4524	Discontinued
0.6644	Remote Similarity	NPD5787	Discontinued
0.6624	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.659	Remote Similarity	NPD1587	Approved
0.6556	Remote Similarity	NPD1896	Approved
0.6552	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD3833	Phase 3
0.6543	Remote Similarity	NPD3835	Phase 3
0.6532	Remote Similarity	NPD7865	Approved
0.6532	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD1592	Phase 3
0.6519	Remote Similarity	NPD5020	Approved
0.6507	Remote Similarity	NPD4811	Discontinued
0.65	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.649	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.649	Remote Similarity	NPD1031	Discontinued
0.6474	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD1871	Approved
0.6442	Remote Similarity	NPD4463	Approved
0.6442	Remote Similarity	NPD4462	Approved
0.6429	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.642	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD482	Approved
0.6414	Remote Similarity	NPD9396	Approved
0.6414	Remote Similarity	NPD9392	Approved
0.6412	Remote Similarity	NPD7864	Approved
0.6412	Remote Similarity	NPD7863	Approved
0.6392	Remote Similarity	NPD786	Approved
0.6392	Remote Similarity	NPD4804	Approved
0.6384	Remote Similarity	NPD2092	Phase 2
0.6384	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD1745	Approved
0.6384	Remote Similarity	NPD2094	Phase 2
0.6384	Remote Similarity	NPD2095	Phase 2
0.6383	Remote Similarity	NPD6176	Phase 1
0.6379	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD1343	Approved
0.6374	Remote Similarity	NPD7866	Approved
0.6373	Remote Similarity	NPD7454	Approved
0.6373	Remote Similarity	NPD7455	Approved
0.6369	Remote Similarity	NPD201	Phase 2
0.6369	Remote Similarity	NPD200	Phase 2
0.6354	Remote Similarity	NPD4499	Approved
0.6348	Remote Similarity	NPD2096	Phase 2
0.6348	Remote Similarity	NPD2091	Phase 2
0.6348	Remote Similarity	NPD1096	Discontinued
0.6348	Remote Similarity	NPD7564	Discontinued
0.6339	Remote Similarity	NPD460	Discontinued
0.6335	Remote Similarity	NPD5254	Discontinued
0.6328	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2008	Discontinued
0.6312	Remote Similarity	NPD4805	Approved
0.631	Remote Similarity	NPD4501	Approved
0.631	Remote Similarity	NPD4500	Approved
0.6307	Remote Similarity	NPD3077	Approved
0.6307	Remote Similarity	NPD3079	Approved
0.6307	Remote Similarity	NPD3076	Approved
0.6307	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD3078	Approved
0.6306	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD4506	Discontinued
0.6296	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD1079	Discontinued
0.6277	Remote Similarity	NPD7727	Phase 2
0.6277	Remote Similarity	NPD7817	Phase 1
0.6271	Remote Similarity	NPD1643	Phase 3
0.627	Remote Similarity	NPD4848	Phase 1
0.6269	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD1262	Discovery
0.6264	Remote Similarity	NPD5686	Approved
0.6264	Remote Similarity	NPD5685	Approved
0.6263	Remote Similarity	NPD5901	Discontinued
0.6263	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD3947	Discontinued
0.625	Remote Similarity	NPD2509	Approved
0.625	Remote Similarity	NPD2510	Approved
0.625	Remote Similarity	NPD9599	Approved
0.625	Remote Similarity	NPD6376	Discontinued
0.625	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD3246	Discontinued
0.6242	Remote Similarity	NPD272	Approved
0.622	Remote Similarity	NPD1270	Approved
0.6218	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD1600	Suspended
0.6216	Remote Similarity	NPD7618	Phase 3
0.6216	Remote Similarity	NPD7619	Phase 3
0.6211	Remote Similarity	NPD1722	Approved
0.6209	Remote Similarity	NPD1534	Approved
0.6203	Remote Similarity	NPD1982	Phase 1
0.6199	Remote Similarity	NPD3583	Phase 2
0.6193	Remote Similarity	NPD3238	Discontinued
0.619	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD5809	Phase 3
0.6188	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD3100	Discontinued
0.6181	Remote Similarity	NPD4823	Approved
0.6181	Remote Similarity	NPD5198	Approved
0.6181	Remote Similarity	NPD4824	Approved
0.6181	Remote Similarity	NPD5199	Approved
0.618	Remote Similarity	NPD3927	Phase 2
0.6178	Remote Similarity	NPD8098	Approved
0.6178	Remote Similarity	NPD8115	Approved
0.6178	Remote Similarity	NPD8283	Approved
0.6178	Remote Similarity	NPD8114	Approved
0.6178	Remote Similarity	NPD56	Approved
0.6178	Remote Similarity	NPD8282	Approved
0.6171	Remote Similarity	NPD750	Phase 2
0.6166	Remote Similarity	NPD8399	Phase 1
0.6166	Remote Similarity	NPD8423	Phase 2
0.6163	Remote Similarity	NPD2915	Discontinued
0.6163	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD2753	Discontinued
0.6154	Remote Similarity	NPD4988	Discontinued
0.615	Remote Similarity	NPD6664	Approved
0.6145	Remote Similarity	NPD2172	Phase 1
0.6141	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD4880	Discontinued
0.6138	Remote Similarity	NPD4600	Approved
0.6138	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD4601	Approved
0.6136	Remote Similarity	NPD4883	Approved
0.6134	Remote Similarity	NPD7941	Phase 3
0.6129	Remote Similarity	NPD1619	Phase 3
0.6129	Remote Similarity	NPD3654	Approved
0.6122	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD8097	Phase 3
0.6122	Remote Similarity	NPD2411	Approved
0.6122	Remote Similarity	NPD8096	Phase 3
0.6111	Remote Similarity	NPD3393	Approved
0.6111	Remote Similarity	NPD3389	Approved
0.6111	Remote Similarity	NPD3394	Approved
0.6111	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD4922	Phase 2
0.6105	Remote Similarity	NPD5017	Discontinued
0.6102	Remote Similarity	NPD4075	Phase 2
0.61	Remote Similarity	NPD6770	Approved
0.6098	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.609	Remote Similarity	NPD3476	Approved
0.609	Remote Similarity	NPD3475	Approved
0.6089	Remote Similarity	NPD2479	Phase 3
0.6089	Remote Similarity	NPD2481	Approved
0.6087	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD6459	Phase 2
0.6082	Remote Similarity	NPD2442	Approved
0.6082	Remote Similarity	NPD2443	Approved
0.6074	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD9724	Phase 1
0.6068	Remote Similarity	NPD5479	Discontinued
0.6065	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6065	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD2880	Discontinued
0.6064	Remote Similarity	NPD5003	Discontinued
0.6062	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD9098	Phase 3
0.6056	Remote Similarity	NPD9099	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD1658	Discontinued
0.6053	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD5400	Approved
0.6043	Remote Similarity	NPD7406	Phase 2
0.6041	Remote Similarity	NPD7657	Approved
0.6041	Remote Similarity	NPD7656	Approved
0.6036	Remote Similarity	NPD2061	Approved
0.6036	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD7459	Phase 2
0.6032	Remote Similarity	NPD7946	Pre-registration
0.603	Remote Similarity	NPD8160	Phase 2
0.6023	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6013	Remote Similarity	NPD9100	Approved
0.6012	Remote Similarity	NPD5138	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