NPASS Compound

Structure

NPC45409 OpenBabel07101719142D 29 29 0 0 1 0 0 0 0 0999 V2000 4.0428 -5.4817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4190 -2.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0549 -7.6959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6786 -10.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3212 -3.1653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9449 -6.0997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0032 -0.5909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5780 -3.8344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1132 -2.1871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7370 -5.1216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9543 -0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8959 -6.4087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3607 -8.0560 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 4.7859 -4.8126 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1622 -1.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1039 -7.3869 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 6.5686 -9.0342 0.0000 C 0 0 2 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 1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5197 -9.3432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8255 -9.7033 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2628 -8.6740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7276 -10.3213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 28 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 16 1 1 6 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 20 24 1 6 0 0 0 21 25 2 0 0 0 0 21 29 1 0 0 0 0 22 26 1 1 0 0 0 22 29 1 0 0 0 0 23 27 2 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.24
Volume:	434.73
LogP:	3.939
LogD:	3.742
LogS:	-4.378
# Rotatable Bonds:	14
TPSA:	96.97
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.269
Synthetic Accessibility Score:	4.211
Fsp3:	0.565
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.785
MDCK Permeability:	2.7237025278736837e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.797

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	95.59442901611328%
Volume Distribution (VD):	0.348
Pgp-substrate:	3.012483835220337%

ADMET: Metabolism

CYP1A2-inhibitor:	0.367
CYP1A2-substrate:	0.907
CYP2C19-inhibitor:	0.567
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.902
CYP2C9-substrate:	0.983
CYP2D6-inhibitor:	0.59
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.196
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	7.082
Half-life (T1/2):	0.785

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.287
Drug-inuced Liver Injury (DILI):	0.714
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.6
Skin Sensitization:	0.927
Carcinogencity:	0.813
Eye Corrosion:	0.068
Eye Irritation:	0.102
Respiratory Toxicity:	0.789

Download Data

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

Natural Product: NPC45409

Natural Product ID:	NPC45409
*Common Name:**	Sarcotin N
IUPAC Name:	methyl (2R,4Z,8S,9E,11E)-2-hydroxy-15-[(2R)-2-hydroxy-5-oxo-2H-furan-3-yl]-4,8,12-trimethylpentadeca-4,9,11-trienoate
Synonyms:	Sarcotin N
Standard InCHIKey:	CXIXHKABKDGPQF-VWAJJWHNSA-N
Standard InCHI:	InChI=1S/C23H34O6/c1-16(10-6-12-18(3)14-20(24)23(27)28-4)8-5-9-17(2)11-7-13-19-15-21(25)29-22(19)26/h5,8-9,12,15-16,20,22,24,26H,6-7,10-11,13-14H2,1-4H3/b8-5+,17-9+,18-12-/t16-,20-,22-/m1/s1
SMILES:	COC(=O)[C@@H](C/C(=CCC[C@@H](/C=C/C=C(/CCCC1=CC(=O)O[C@H]1O)C)C)/C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461180
PubChem CID:	10024319
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO33166	Sarcotragus	Genus	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640517]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	19.4	ug ml-1	PMID[486019]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[486019]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	10.9	ug ml-1	PMID[486019]
NPT574	Cell Line	XF498	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[486019]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	21.7	ug ml-1	PMID[486019]

☑ 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 NPC45409 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	187
0.1-0.2	1177
0.2-0.3	5107
0.3-0.4	13380
0.4-0.5	13337
0.5-0.6	6746
0.6-0.7	2353
0.7-0.8	400
0.8-0.85	4
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC475879
0.875	High Similarity	NPC474098
0.875	High Similarity	NPC475995
0.8706	High Similarity	NPC475706
0.8523	High Similarity	NPC475739
0.8391	Intermediate Similarity	NPC474424
0.8372	Intermediate Similarity	NPC475714
0.8046	Intermediate Similarity	NPC474028
0.8046	Intermediate Similarity	NPC474439
0.7952	Intermediate Similarity	NPC315843
0.7952	Intermediate Similarity	NPC107654
0.7865	Intermediate Similarity	NPC161670
0.7805	Intermediate Similarity	NPC473361
0.7805	Intermediate Similarity	NPC329904
0.7778	Intermediate Similarity	NPC471494
0.7727	Intermediate Similarity	NPC112868
0.7711	Intermediate Similarity	NPC316185
0.7701	Intermediate Similarity	NPC321728
0.7701	Intermediate Similarity	NPC99651
0.7692	Intermediate Similarity	NPC311163
0.7683	Intermediate Similarity	NPC475004
0.764	Intermediate Similarity	NPC471298
0.764	Intermediate Similarity	NPC324170
0.764	Intermediate Similarity	NPC471296
0.7634	Intermediate Similarity	NPC139418
0.7586	Intermediate Similarity	NPC108816
0.7586	Intermediate Similarity	NPC93763
0.7582	Intermediate Similarity	NPC21469
0.7579	Intermediate Similarity	NPC238090
0.7579	Intermediate Similarity	NPC469692
0.7579	Intermediate Similarity	NPC472196
0.7579	Intermediate Similarity	NPC469645
0.7579	Intermediate Similarity	NPC472195
0.7561	Intermediate Similarity	NPC474823
0.7556	Intermediate Similarity	NPC253801
0.7556	Intermediate Similarity	NPC284472
0.7556	Intermediate Similarity	NPC471297
0.7556	Intermediate Similarity	NPC286770
0.7556	Intermediate Similarity	NPC229799
0.7553	Intermediate Similarity	NPC473904
0.7553	Intermediate Similarity	NPC473448
0.7551	Intermediate Similarity	NPC161855
0.7551	Intermediate Similarity	NPC475653
0.7551	Intermediate Similarity	NPC203627
0.7529	Intermediate Similarity	NPC470686
0.7528	Intermediate Similarity	NPC325031
0.7526	Intermediate Similarity	NPC473291
0.7526	Intermediate Similarity	NPC255410
0.75	Intermediate Similarity	NPC159698
0.75	Intermediate Similarity	NPC471537
0.75	Intermediate Similarity	NPC471599
0.75	Intermediate Similarity	NPC211892
0.75	Intermediate Similarity	NPC261721
0.75	Intermediate Similarity	NPC473596
0.75	Intermediate Similarity	NPC279267
0.75	Intermediate Similarity	NPC208473
0.75	Intermediate Similarity	NPC470255
0.75	Intermediate Similarity	NPC69082
0.75	Intermediate Similarity	NPC121825
0.7475	Intermediate Similarity	NPC477720
0.7473	Intermediate Similarity	NPC475035
0.7473	Intermediate Similarity	NPC266718
0.7473	Intermediate Similarity	NPC471301
0.7473	Intermediate Similarity	NPC473308
0.7471	Intermediate Similarity	NPC7563
0.7471	Intermediate Similarity	NPC320630
0.7471	Intermediate Similarity	NPC116177
0.7451	Intermediate Similarity	NPC469852
0.7451	Intermediate Similarity	NPC472749
0.7451	Intermediate Similarity	NPC472751
0.7449	Intermediate Similarity	NPC120299
0.7444	Intermediate Similarity	NPC11332
0.7444	Intermediate Similarity	NPC310450
0.7444	Intermediate Similarity	NPC73310
0.7444	Intermediate Similarity	NPC473712
0.7444	Intermediate Similarity	NPC474959
0.7444	Intermediate Similarity	NPC475046
0.7444	Intermediate Similarity	NPC475159
0.7444	Intermediate Similarity	NPC180363
0.7444	Intermediate Similarity	NPC145914
0.7444	Intermediate Similarity	NPC473529
0.7444	Intermediate Similarity	NPC323251
0.7444	Intermediate Similarity	NPC94875
0.7444	Intermediate Similarity	NPC329829
0.7444	Intermediate Similarity	NPC131002
0.7444	Intermediate Similarity	NPC473780
0.7444	Intermediate Similarity	NPC11383
0.7444	Intermediate Similarity	NPC65930
0.7442	Intermediate Similarity	NPC260396
0.7442	Intermediate Similarity	NPC478192
0.7442	Intermediate Similarity	NPC478196
0.7442	Intermediate Similarity	NPC478195
0.7442	Intermediate Similarity	NPC478194
0.7442	Intermediate Similarity	NPC478193
0.7442	Intermediate Similarity	NPC478191
0.7426	Intermediate Similarity	NPC472750
0.7426	Intermediate Similarity	NPC472747
0.7423	Intermediate Similarity	NPC300710
0.7419	Intermediate Similarity	NPC313658
0.7419	Intermediate Similarity	NPC316138
0.7419	Intermediate Similarity	NPC475678
0.74	Intermediate Similarity	NPC20673
0.74	Intermediate Similarity	NPC219038
0.7396	Intermediate Similarity	NPC282644
0.7396	Intermediate Similarity	NPC473723
0.7396	Intermediate Similarity	NPC475173
0.7396	Intermediate Similarity	NPC320552
0.7396	Intermediate Similarity	NPC473561
0.7396	Intermediate Similarity	NPC11456
0.7396	Intermediate Similarity	NPC29798
0.7396	Intermediate Similarity	NPC473663
0.7391	Intermediate Similarity	NPC475034
0.7391	Intermediate Similarity	NPC11804
0.7391	Intermediate Similarity	NPC82795
0.7391	Intermediate Similarity	NPC286338
0.7391	Intermediate Similarity	NPC66346
0.7391	Intermediate Similarity	NPC322529
0.7391	Intermediate Similarity	NPC471300
0.7391	Intermediate Similarity	NPC283085
0.7391	Intermediate Similarity	NPC471223
0.7391	Intermediate Similarity	NPC473478
0.7391	Intermediate Similarity	NPC473669
0.7391	Intermediate Similarity	NPC474860
0.7391	Intermediate Similarity	NPC182383
0.7391	Intermediate Similarity	NPC231009
0.7391	Intermediate Similarity	NPC103284
0.7391	Intermediate Similarity	NPC107986
0.7391	Intermediate Similarity	NPC67081
0.7391	Intermediate Similarity	NPC473651
0.7391	Intermediate Similarity	NPC223871
0.7391	Intermediate Similarity	NPC132496
0.7391	Intermediate Similarity	NPC110710
0.7391	Intermediate Similarity	NPC1083
0.7386	Intermediate Similarity	NPC267231
0.7381	Intermediate Similarity	NPC4299
0.7379	Intermediate Similarity	NPC469853
0.7368	Intermediate Similarity	NPC327253
0.7368	Intermediate Similarity	NPC281942
0.7368	Intermediate Similarity	NPC474761
0.7368	Intermediate Similarity	NPC476004
0.7368	Intermediate Similarity	NPC118078
0.7368	Intermediate Similarity	NPC232426
0.7368	Intermediate Similarity	NPC473311
0.7368	Intermediate Similarity	NPC316228
0.7363	Intermediate Similarity	NPC144415
0.7363	Intermediate Similarity	NPC169575
0.7363	Intermediate Similarity	NPC40746
0.7363	Intermediate Similarity	NPC16488
0.7363	Intermediate Similarity	NPC142111
0.7363	Intermediate Similarity	NPC161045
0.7363	Intermediate Similarity	NPC473315
0.7353	Intermediate Similarity	NPC472748
0.7347	Intermediate Similarity	NPC288350
0.7347	Intermediate Similarity	NPC173329
0.7347	Intermediate Similarity	NPC306041
0.734	Intermediate Similarity	NPC470137
0.7333	Intermediate Similarity	NPC315731
0.7333	Intermediate Similarity	NPC474894
0.7326	Intermediate Similarity	NPC227396
0.732	Intermediate Similarity	NPC294293
0.7312	Intermediate Similarity	NPC114694
0.7312	Intermediate Similarity	NPC231096
0.7312	Intermediate Similarity	NPC240695
0.7312	Intermediate Similarity	NPC134865
0.7312	Intermediate Similarity	NPC134807
0.7312	Intermediate Similarity	NPC61527
0.7312	Intermediate Similarity	NPC219498
0.7312	Intermediate Similarity	NPC171174
0.7312	Intermediate Similarity	NPC475581
0.7312	Intermediate Similarity	NPC103523
0.7312	Intermediate Similarity	NPC164393
0.7312	Intermediate Similarity	NPC316426
0.7312	Intermediate Similarity	NPC473687
0.7312	Intermediate Similarity	NPC204686
0.7312	Intermediate Similarity	NPC62118
0.7312	Intermediate Similarity	NPC142117
0.7312	Intermediate Similarity	NPC469483
0.7312	Intermediate Similarity	NPC469910
0.7312	Intermediate Similarity	NPC309211
0.7312	Intermediate Similarity	NPC47937
0.7312	Intermediate Similarity	NPC308412
0.7312	Intermediate Similarity	NPC112685
0.7312	Intermediate Similarity	NPC107717
0.7312	Intermediate Similarity	NPC315395
0.7312	Intermediate Similarity	NPC134885
0.7312	Intermediate Similarity	NPC210218
0.7312	Intermediate Similarity	NPC232555
0.7303	Intermediate Similarity	NPC475210
0.7303	Intermediate Similarity	NPC1180
0.73	Intermediate Similarity	NPC469864
0.73	Intermediate Similarity	NPC244878
0.73	Intermediate Similarity	NPC469872
0.7294	Intermediate Similarity	NPC477086
0.7294	Intermediate Similarity	NPC477087
0.7292	Intermediate Similarity	NPC141831
0.7292	Intermediate Similarity	NPC472010
0.7292	Intermediate Similarity	NPC472197
0.7292	Intermediate Similarity	NPC473707
0.7292	Intermediate Similarity	NPC472199
0.7292	Intermediate Similarity	NPC473321

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 NPC45409 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	1623
0.2-0.3	3803
0.3-0.4	2506
0.4-0.5	787
0.5-0.6	219
0.6-0.7	50
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
0.7374	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7838	Discovery
0.7283	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6698	Approved
0.7188	Intermediate Similarity	NPD46	Approved
0.7113	Intermediate Similarity	NPD7983	Approved
0.7033	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7154	Phase 3
0.6981	Remote Similarity	NPD6686	Approved
0.6914	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5785	Approved
0.6813	Remote Similarity	NPD4268	Approved
0.6813	Remote Similarity	NPD4271	Approved
0.6809	Remote Similarity	NPD5362	Discontinued
0.6789	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4756	Discovery
0.6702	Remote Similarity	NPD5209	Approved
0.6699	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD5363	Approved
0.6667	Remote Similarity	NPD7839	Suspended
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD3197	Phase 1
0.6667	Remote Similarity	NPD4822	Approved
0.6632	Remote Similarity	NPD5332	Approved
0.6632	Remote Similarity	NPD5331	Approved
0.6632	Remote Similarity	NPD6110	Phase 1
0.6628	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4790	Discontinued
0.6574	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8517	Approved
0.6552	Remote Similarity	NPD8515	Approved
0.6552	Remote Similarity	NPD8513	Phase 3
0.6552	Remote Similarity	NPD8516	Approved
0.6535	Remote Similarity	NPD5778	Approved
0.6535	Remote Similarity	NPD5779	Approved
0.6531	Remote Similarity	NPD4250	Approved
0.6531	Remote Similarity	NPD4251	Approved
0.6526	Remote Similarity	NPD4270	Approved
0.6526	Remote Similarity	NPD4269	Approved
0.6495	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4252	Approved
0.6486	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6109	Phase 1
0.6452	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7637	Suspended
0.6429	Remote Similarity	NPD4249	Approved
0.6429	Remote Similarity	NPD5786	Approved
0.6415	Remote Similarity	NPD5344	Discontinued
0.6396	Remote Similarity	NPD6371	Approved
0.6321	Remote Similarity	NPD7640	Approved
0.6321	Remote Similarity	NPD6648	Approved
0.6321	Remote Similarity	NPD7639	Approved
0.6304	Remote Similarity	NPD8039	Approved
0.6303	Remote Similarity	NPD7829	Approved
0.6303	Remote Similarity	NPD7830	Approved
0.6296	Remote Similarity	NPD6647	Phase 2
0.6283	Remote Similarity	NPD969	Suspended
0.625	Remote Similarity	NPD5369	Approved
0.625	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6101	Approved
0.6238	Remote Similarity	NPD5370	Suspended
0.6226	Remote Similarity	NPD7638	Approved
0.6207	Remote Similarity	NPD7115	Discovery
0.6207	Remote Similarity	NPD7505	Discontinued
0.6207	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6435	Approved
0.6186	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7641	Discontinued
0.6146	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD7503	Approved
0.6134	Remote Similarity	NPD8444	Approved
0.6117	Remote Similarity	NPD6411	Approved
0.6117	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD2067	Discontinued
0.6071	Remote Similarity	NPD9119	Approved
0.6071	Remote Similarity	NPD69	Approved
0.6066	Remote Similarity	NPD7507	Approved
0.6017	Remote Similarity	NPD7328	Approved
0.6017	Remote Similarity	NPD7327	Approved
0.6016	Remote Similarity	NPD8074	Phase 3
0.6	Remote Similarity	NPD8033	Approved
0.6	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6412	Phase 2
0.5979	Remote Similarity	NPD5368	Approved
0.5966	Remote Similarity	NPD7516	Approved
0.5952	Remote Similarity	NPD9118	Approved
0.595	Remote Similarity	NPD7623	Phase 3
0.595	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD8451	Approved
0.5932	Remote Similarity	NPD7500	Approved
0.5922	Remote Similarity	NPD689	Discontinued
0.592	Remote Similarity	NPD7319	Approved
0.5917	Remote Similarity	NPD8377	Approved
0.5917	Remote Similarity	NPD8294	Approved
0.5902	Remote Similarity	NPD7642	Approved
0.5887	Remote Similarity	NPD8448	Approved
0.5882	Remote Similarity	NPD7524	Approved
0.5868	Remote Similarity	NPD8296	Approved
0.5868	Remote Similarity	NPD8335	Approved
0.5868	Remote Similarity	NPD8378	Approved
0.5868	Remote Similarity	NPD8380	Approved
0.5868	Remote Similarity	NPD8379	Approved
0.5854	Remote Similarity	NPD8341	Approved
0.5854	Remote Similarity	NPD8299	Approved
0.5854	Remote Similarity	NPD8340	Approved
0.5854	Remote Similarity	NPD8342	Approved
0.5847	Remote Similarity	NPD2629	Approved
0.5846	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD1694	Approved
0.5842	Remote Similarity	NPD1696	Phase 3
0.5833	Remote Similarity	NPD6083	Phase 2
0.5833	Remote Similarity	NPD6084	Phase 2
0.5802	Remote Similarity	NPD6927	Phase 3
0.5784	Remote Similarity	NPD5279	Phase 3
0.5778	Remote Similarity	NPD3704	Approved
0.5776	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD2204	Approved
0.5766	Remote Similarity	NPD7632	Discontinued
0.576	Remote Similarity	NPD7746	Phase 1
0.576	Remote Similarity	NPD7747	Phase 1
0.5752	Remote Similarity	NPD4211	Phase 1
0.5748	Remote Similarity	NPD8391	Approved
0.5748	Remote Similarity	NPD8392	Approved
0.5748	Remote Similarity	NPD8390	Approved
0.5739	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.573	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD8297	Approved
0.5726	Remote Similarity	NPD6882	Approved
0.5726	Remote Similarity	NPD6053	Discontinued
0.5714	Remote Similarity	NPD690	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5703	Remote Similarity	NPD7260	Phase 2
0.5701	Remote Similarity	NPD5282	Discontinued
0.5698	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD8080	Discontinued
0.569	Remote Similarity	NPD6421	Discontinued
0.568	Remote Similarity	NPD8273	Phase 1
0.5673	Remote Similarity	NPD6672	Approved
0.5673	Remote Similarity	NPD5737	Approved
0.5652	Remote Similarity	NPD6899	Approved
0.5652	Remote Similarity	NPD6881	Approved
0.5648	Remote Similarity	NPD5695	Phase 3
0.5645	Remote Similarity	NPD8328	Phase 3
0.5644	Remote Similarity	NPD6695	Phase 3
0.5636	Remote Similarity	NPD9495	Approved
0.5631	Remote Similarity	NPD6422	Discontinued
0.5625	Remote Similarity	NPD8264	Approved
0.562	Remote Similarity	NPD694	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD6402	Approved
0.5614	Remote Similarity	NPD7128	Approved
0.5614	Remote Similarity	NPD5739	Approved
0.5614	Remote Similarity	NPD6675	Approved
0.5612	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD6399	Phase 3
0.5604	Remote Similarity	NPD6108	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