NPASS Compound

Structure

NPC475739 OpenBabel07101719252D 31 32 0 0 1 0 0 0 0 0999 V2000 -5.5388 2.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0388 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0388 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2707 -3.9432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0388 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5388 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0388 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5388 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0388 2.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0388 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5388 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0388 2.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0388 0.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.3752 -2.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0388 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -8.6321 -2.2796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2413 -2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6540 -2.4875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1548 -2.8554 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 -10.0334 -1.4706 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 1 16 1 0 0 0 0 2 17 1 0 0 0 0 4 19 1 0 0 0 0 5 8 1 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 2 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 20 1 0 0 0 0 14 18 1 0 0 0 0 14 21 2 0 0 0 0 15 20 2 0 0 0 0 15 22 1 0 0 0 0 18 3 1 6 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 23 1 0 0 0 0 21 30 1 0 0 0 0 22 26 1 0 0 0 0 22 31 1 0 0 0 0 23 27 1 0 0 0 0 24 28 2 0 0 0 0 24 30 1 0 0 0 0 25 29 2 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.24
Volume:	458.129
LogP:	4.092
LogD:	3.653
LogS:	-3.937
# Rotatable Bonds:	11
TPSA:	107.2
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.289
Synthetic Accessibility Score:	3.784
Fsp3:	0.44
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.056
MDCK Permeability:	1.3867229426978156e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.722
Human Intestinal Absorption (HIA):	0.502
20% Bioavailability (F20%):	0.812
30% Bioavailability (F30%):	0.117

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	99.6957015991211%
Volume Distribution (VD):	2.693
Pgp-substrate:	0.753937840461731%

ADMET: Metabolism

CYP1A2-inhibitor:	0.262
CYP1A2-substrate:	0.923
CYP2C19-inhibitor:	0.089
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.624
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.629
CYP2D6-substrate:	0.911
CYP3A4-inhibitor:	0.05
CYP3A4-substrate:	0.137

ADMET: Excretion

Clearance (CL):	5.502
Half-life (T1/2):	0.963

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.473
Drug-inuced Liver Injury (DILI):	0.457
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.645
Skin Sensitization:	0.916
Carcinogencity:	0.648
Eye Corrosion:	0.006
Eye Irritation:	0.685
Respiratory Toxicity:	0.097

Download Data

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

Natural Product: NPC475739

Natural Product ID:	NPC475739
*Common Name:**	5-Hydroxy-3-((R,4Z,8Z)-13-(3-Hydroxy-4-Methyl-5-Oxofuran-2(5H)-Ylidene)-4,8,12-Trimethyltrideca-4,8-Dienyl)Furan-2(5H)-One
IUPAC Name:	(5Z)-4-hydroxy-5-[(2R,5Z,9Z)-13-(2-hydroxy-5-oxo-2H-furan-4-yl)-2,6,10-trimethyltrideca-5,9-dienylidene]-3-methylfuran-2-one
Synonyms:
Standard InCHIKey:	NIYLZGMUFLNCHW-MTQZVVNSSA-N
Standard InCHI:	InChI=1S/C25H34O6/c1-16(10-6-12-18(3)14-21-23(27)19(4)24(28)30-21)8-5-9-17(2)11-7-13-20-15-22(26)31-25(20)29/h9-10,14-15,18,22,26-27H,5-8,11-13H2,1-4H3/b16-10-,17-9-,21-14-/t18-,22?/m1/s1
SMILES:	CC1=C(C(=CC(C)CCC=C(C)CCC=C(C)CCCC2=CC(OC2=O)O)OC1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513507
PubChem CID:	54729897
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
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678655]
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350153]
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18341287]

☑ 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
MIC	9
Others	1

Activity Type	# Activity
Cell Line	1
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	>	100.0	ug.mL-1	PMID[569901]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	100.0	ug.mL-1	PMID[569901]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[569901]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[569901]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[569901]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[569901]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[569901]

☑ 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 NPC475739 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	189
0.1-0.2	1274
0.2-0.3	5426
0.3-0.4	13545
0.4-0.5	14098
0.5-0.6	6102
0.6-0.7	1813
0.7-0.8	238
0.8-0.85	4
0.85-0.9	2
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9398	High Similarity	NPC474424
0.9277	High Similarity	NPC475706
0.9157	High Similarity	NPC475714
0.908	High Similarity	NPC474098
0.908	High Similarity	NPC475995
0.881	High Similarity	NPC474028
0.881	High Similarity	NPC474439
0.8523	High Similarity	NPC45409
0.8242	Intermediate Similarity	NPC475879
0.7753	Intermediate Similarity	NPC329829
0.7753	Intermediate Similarity	NPC473712
0.7753	Intermediate Similarity	NPC131002
0.7753	Intermediate Similarity	NPC473780
0.7753	Intermediate Similarity	NPC65930
0.7753	Intermediate Similarity	NPC94875
0.7753	Intermediate Similarity	NPC11332
0.7753	Intermediate Similarity	NPC145914
0.7753	Intermediate Similarity	NPC73310
0.7753	Intermediate Similarity	NPC473529
0.7753	Intermediate Similarity	NPC475159
0.7753	Intermediate Similarity	NPC180363
0.7753	Intermediate Similarity	NPC471296
0.7742	Intermediate Similarity	NPC139418
0.7717	Intermediate Similarity	NPC475678
0.7667	Intermediate Similarity	NPC253801
0.7667	Intermediate Similarity	NPC144415
0.766	Intermediate Similarity	NPC473904
0.7619	Intermediate Similarity	NPC84038
0.7586	Intermediate Similarity	NPC68156
0.7582	Intermediate Similarity	NPC163093
0.7582	Intermediate Similarity	NPC156804
0.7529	Intermediate Similarity	NPC474705
0.75	Intermediate Similarity	NPC39167
0.75	Intermediate Similarity	NPC475173
0.75	Intermediate Similarity	NPC21469
0.75	Intermediate Similarity	NPC473663
0.75	Intermediate Similarity	NPC475268
0.75	Intermediate Similarity	NPC329838
0.75	Intermediate Similarity	NPC292809
0.75	Intermediate Similarity	NPC93763
0.75	Intermediate Similarity	NPC477018
0.75	Intermediate Similarity	NPC473156
0.75	Intermediate Similarity	NPC103284
0.75	Intermediate Similarity	NPC231009
0.75	Intermediate Similarity	NPC473671
0.75	Intermediate Similarity	NPC473520
0.75	Intermediate Similarity	NPC473669
0.75	Intermediate Similarity	NPC329615
0.75	Intermediate Similarity	NPC471300
0.75	Intermediate Similarity	NPC477014
0.75	Intermediate Similarity	NPC202055
0.75	Intermediate Similarity	NPC82795
0.75	Intermediate Similarity	NPC322529
0.75	Intermediate Similarity	NPC120398
0.75	Intermediate Similarity	NPC108816
0.75	Intermediate Similarity	NPC477013
0.75	Intermediate Similarity	NPC235809
0.75	Intermediate Similarity	NPC473723
0.75	Intermediate Similarity	NPC39279
0.75	Intermediate Similarity	NPC474860
0.75	Intermediate Similarity	NPC132496
0.75	Intermediate Similarity	NPC110710
0.75	Intermediate Similarity	NPC223871
0.75	Intermediate Similarity	NPC77871
0.75	Intermediate Similarity	NPC25764
0.75	Intermediate Similarity	NPC107986
0.75	Intermediate Similarity	NPC66346
0.75	Intermediate Similarity	NPC11456
0.75	Intermediate Similarity	NPC471567
0.75	Intermediate Similarity	NPC283085
0.75	Intermediate Similarity	NPC67183
0.75	Intermediate Similarity	NPC1083
0.75	Intermediate Similarity	NPC100921
0.75	Intermediate Similarity	NPC470400
0.75	Intermediate Similarity	NPC473561
0.75	Intermediate Similarity	NPC473651
0.75	Intermediate Similarity	NPC9678
0.75	Intermediate Similarity	NPC319036
0.75	Intermediate Similarity	NPC286338
0.75	Intermediate Similarity	NPC473478
0.7474	Intermediate Similarity	NPC473448
0.7473	Intermediate Similarity	NPC475947
0.7471	Intermediate Similarity	NPC123360
0.7442	Intermediate Similarity	NPC470686
0.7419	Intermediate Similarity	NPC25703
0.7419	Intermediate Similarity	NPC219498
0.7419	Intermediate Similarity	NPC232555
0.7419	Intermediate Similarity	NPC469483
0.7419	Intermediate Similarity	NPC241360
0.7419	Intermediate Similarity	NPC69082
0.7419	Intermediate Similarity	NPC279267
0.7419	Intermediate Similarity	NPC477015
0.7419	Intermediate Similarity	NPC142117
0.7419	Intermediate Similarity	NPC240695
0.7419	Intermediate Similarity	NPC134865
0.7419	Intermediate Similarity	NPC112685
0.7419	Intermediate Similarity	NPC475581
0.7419	Intermediate Similarity	NPC231096
0.7419	Intermediate Similarity	NPC293136
0.7419	Intermediate Similarity	NPC134807
0.7419	Intermediate Similarity	NPC103523
0.7419	Intermediate Similarity	NPC477010
0.7419	Intermediate Similarity	NPC132940
0.7419	Intermediate Similarity	NPC308412
0.7419	Intermediate Similarity	NPC210218
0.7419	Intermediate Similarity	NPC204686
0.7419	Intermediate Similarity	NPC309211
0.7419	Intermediate Similarity	NPC282815
0.7419	Intermediate Similarity	NPC114694
0.7419	Intermediate Similarity	NPC107717
0.7419	Intermediate Similarity	NPC473687
0.7419	Intermediate Similarity	NPC164393
0.7419	Intermediate Similarity	NPC134885
0.7419	Intermediate Similarity	NPC219652
0.7419	Intermediate Similarity	NPC473840
0.7419	Intermediate Similarity	NPC171174
0.7419	Intermediate Similarity	NPC62118
0.7396	Intermediate Similarity	NPC477783
0.7396	Intermediate Similarity	NPC473707
0.7391	Intermediate Similarity	NPC243618
0.7391	Intermediate Similarity	NPC70424
0.7386	Intermediate Similarity	NPC7563
0.7386	Intermediate Similarity	NPC116177
0.7386	Intermediate Similarity	NPC316324
0.7386	Intermediate Similarity	NPC320630
0.7368	Intermediate Similarity	NPC251528
0.7363	Intermediate Similarity	NPC474291
0.7356	Intermediate Similarity	NPC478194
0.7356	Intermediate Similarity	NPC478191
0.7356	Intermediate Similarity	NPC478195
0.7356	Intermediate Similarity	NPC478193
0.7356	Intermediate Similarity	NPC478196
0.7356	Intermediate Similarity	NPC469414
0.7356	Intermediate Similarity	NPC329826
0.7356	Intermediate Similarity	NPC478192
0.7347	Intermediate Similarity	NPC476487
0.7347	Intermediate Similarity	NPC476488
0.734	Intermediate Similarity	NPC178215
0.734	Intermediate Similarity	NPC154097
0.734	Intermediate Similarity	NPC20533
0.734	Intermediate Similarity	NPC473995
0.734	Intermediate Similarity	NPC476583
0.734	Intermediate Similarity	NPC159750
0.734	Intermediate Similarity	NPC258068
0.734	Intermediate Similarity	NPC470401
0.734	Intermediate Similarity	NPC473649
0.734	Intermediate Similarity	NPC477012
0.732	Intermediate Similarity	NPC59646
0.7312	Intermediate Similarity	NPC182383
0.73	Intermediate Similarity	NPC187268
0.7292	Intermediate Similarity	NPC477782
0.7292	Intermediate Similarity	NPC474232
0.7292	Intermediate Similarity	NPC166554
0.7292	Intermediate Similarity	NPC476004
0.7292	Intermediate Similarity	NPC474761
0.7283	Intermediate Similarity	NPC40746
0.7283	Intermediate Similarity	NPC169575
0.7273	Intermediate Similarity	NPC306041
0.7263	Intermediate Similarity	NPC48338
0.7263	Intermediate Similarity	NPC133730
0.7263	Intermediate Similarity	NPC151403
0.7263	Intermediate Similarity	NPC20339
0.7263	Intermediate Similarity	NPC39754
0.7263	Intermediate Similarity	NPC40376
0.7263	Intermediate Similarity	NPC320458
0.7263	Intermediate Similarity	NPC171135
0.7263	Intermediate Similarity	NPC169511
0.7263	Intermediate Similarity	NPC81045
0.7263	Intermediate Similarity	NPC473905
0.7263	Intermediate Similarity	NPC61257
0.7263	Intermediate Similarity	NPC287164
0.7263	Intermediate Similarity	NPC261952
0.7263	Intermediate Similarity	NPC234077
0.7263	Intermediate Similarity	NPC233551
0.7263	Intermediate Similarity	NPC191929
0.7263	Intermediate Similarity	NPC21208
0.7263	Intermediate Similarity	NPC320569
0.7263	Intermediate Similarity	NPC274446
0.7263	Intermediate Similarity	NPC89001
0.7263	Intermediate Similarity	NPC242364
0.7263	Intermediate Similarity	NPC280621
0.7263	Intermediate Similarity	NPC172821
0.7263	Intermediate Similarity	NPC100454
0.7255	Intermediate Similarity	NPC471599
0.7253	Intermediate Similarity	NPC42470
0.7253	Intermediate Similarity	NPC325031
0.7245	Intermediate Similarity	NPC470521
0.7245	Intermediate Similarity	NPC475572
0.7241	Intermediate Similarity	NPC140287
0.7241	Intermediate Similarity	NPC107654
0.7241	Intermediate Similarity	NPC315843
0.7241	Intermediate Similarity	NPC476355
0.7234	Intermediate Similarity	NPC469910
0.7234	Intermediate Similarity	NPC47937
0.7228	Intermediate Similarity	NPC477720
0.7228	Intermediate Similarity	NPC469872
0.7228	Intermediate Similarity	NPC469864
0.7216	Intermediate Similarity	NPC473321
0.7212	Intermediate Similarity	NPC153095
0.7204	Intermediate Similarity	NPC9868

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 NPC475739 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1817
0.2-0.3	3851
0.3-0.4	2357
0.4-0.5	766
0.5-0.6	170
0.6-0.7	21
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
0.7075	Intermediate Similarity	NPD6686	Approved
0.6939	Remote Similarity	NPD46	Approved
0.6939	Remote Similarity	NPD6698	Approved
0.6915	Remote Similarity	NPD7154	Phase 3
0.6813	Remote Similarity	NPD4756	Discovery
0.6796	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7838	Discovery
0.67	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5785	Approved
0.6562	Remote Similarity	NPD5362	Discontinued
0.6458	Remote Similarity	NPD5209	Approved
0.6429	Remote Similarity	NPD5363	Approved
0.6413	Remote Similarity	NPD8039	Approved
0.6364	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6371	Approved
0.6321	Remote Similarity	NPD4225	Approved
0.63	Remote Similarity	NPD4251	Approved
0.63	Remote Similarity	NPD4250	Approved
0.6286	Remote Similarity	NPD7839	Suspended
0.6283	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD6110	Phase 1
0.6218	Remote Similarity	NPD8513	Phase 3
0.6218	Remote Similarity	NPD8515	Approved
0.6218	Remote Similarity	NPD8516	Approved
0.6218	Remote Similarity	NPD8517	Approved
0.6211	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4249	Approved
0.619	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5778	Approved
0.6154	Remote Similarity	NPD5779	Approved
0.6148	Remote Similarity	NPD7507	Approved
0.614	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4270	Approved
0.6122	Remote Similarity	NPD4269	Approved
0.6116	Remote Similarity	NPD7830	Approved
0.6116	Remote Similarity	NPD7829	Approved
0.61	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7503	Approved
0.6082	Remote Similarity	NPD4252	Approved
0.6061	Remote Similarity	NPD5331	Approved
0.6061	Remote Similarity	NPD5332	Approved
0.6042	Remote Similarity	NPD4268	Approved
0.6042	Remote Similarity	NPD4271	Approved
0.604	Remote Similarity	NPD5786	Approved
0.6023	Remote Similarity	NPD3197	Phase 1
0.602	Remote Similarity	NPD4790	Discontinued
0.6017	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD7641	Discontinued
0.5963	Remote Similarity	NPD6648	Approved
0.5963	Remote Similarity	NPD7639	Approved
0.5963	Remote Similarity	NPD7640	Approved
0.596	Remote Similarity	NPD6435	Approved
0.5955	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6053	Discontinued
0.5946	Remote Similarity	NPD6647	Phase 2
0.5941	Remote Similarity	NPD1694	Approved
0.5929	Remote Similarity	NPD6412	Phase 2
0.5918	Remote Similarity	NPD4821	Approved
0.5918	Remote Similarity	NPD4820	Approved
0.5918	Remote Similarity	NPD4819	Approved
0.5918	Remote Similarity	NPD4822	Approved
0.5913	Remote Similarity	NPD2067	Discontinued
0.5909	Remote Similarity	NPD5344	Discontinued
0.5882	Remote Similarity	NPD7505	Discontinued
0.5872	Remote Similarity	NPD7638	Approved
0.5865	Remote Similarity	NPD6101	Approved
0.5865	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD5369	Approved
0.5833	Remote Similarity	NPD7327	Approved
0.5833	Remote Similarity	NPD7328	Approved
0.582	Remote Similarity	NPD8444	Approved
0.5798	Remote Similarity	NPD690	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD7516	Approved
0.5772	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD7623	Phase 3
0.5758	Remote Similarity	NPD5368	Approved
0.5755	Remote Similarity	NPD7637	Suspended
0.5755	Remote Similarity	NPD6411	Approved
0.5752	Remote Similarity	NPD5909	Discontinued
0.575	Remote Similarity	NPD7500	Approved
0.5738	Remote Similarity	NPD8294	Approved
0.5738	Remote Similarity	NPD8377	Approved
0.5732	Remote Similarity	NPD6927	Phase 3
0.5726	Remote Similarity	NPD7642	Approved
0.5714	Remote Similarity	NPD8074	Phase 3
0.5714	Remote Similarity	NPD1695	Approved
0.5714	Remote Similarity	NPD3704	Approved
0.5714	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5370	Suspended
0.5691	Remote Similarity	NPD8033	Approved
0.5691	Remote Similarity	NPD8296	Approved
0.5691	Remote Similarity	NPD8380	Approved
0.5691	Remote Similarity	NPD8378	Approved
0.5691	Remote Similarity	NPD8335	Approved
0.5691	Remote Similarity	NPD8379	Approved
0.569	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD969	Suspended
0.5636	Remote Similarity	NPD6083	Phase 2
0.5636	Remote Similarity	NPD6084	Phase 2
0.5635	Remote Similarity	NPD8451	Approved
0.5619	Remote Similarity	NPD6903	Approved
0.5619	Remote Similarity	NPD6672	Approved
0.5619	Remote Similarity	NPD5737	Approved
0.5607	Remote Similarity	NPD4810	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