NPASS Compound

Structure

NPC88877 OpenBabel07101718282D 22 22 0 0 1 0 0 0 0 0999 V2000 -2.0981 -6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8301 -6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -1.5388 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 0.5000 -4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -3.0388 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 -2.9641 -5.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -2.5388 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 1.3660 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 -2.5388 0.0000 C 0 0 1 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 2.2321 -4.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -4.5388 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -3.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 12 2 0 0 0 0 5 13 1 0 0 0 0 6 10 2 0 0 0 0 6 14 1 0 0 0 0 7 11 1 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 9 15 1 0 0 0 0 9 21 1 0 0 0 0 12 15 1 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 13 22 1 0 0 0 0 14 19 2 0 0 0 0 15 16 1 6 0 0 0 16 8 1 1 0 0 0 16 22 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.15
Volume:	322.164
LogP:	2.083
LogD:	1.778
LogS:	-2.665
# Rotatable Bonds:	7
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.428
Synthetic Accessibility Score:	4.286
Fsp3:	0.471
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.559
MDCK Permeability:	4.9855971155921e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.184
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.586
Plasma Protein Binding (PPB):	56.19696044921875%
Volume Distribution (VD):	0.619
Pgp-substrate:	54.877037048339844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.425
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.617
CYP2C19-substrate:	0.527
CYP2C9-inhibitor:	0.472
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.123
CYP3A4-inhibitor:	0.128
CYP3A4-substrate:	0.247

ADMET: Excretion

Clearance (CL):	8.798
Half-life (T1/2):	0.771

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.16
Drug-inuced Liver Injury (DILI):	0.802
AMES Toxicity:	0.307
Rat Oral Acute Toxicity:	0.954
Maximum Recommended Daily Dose:	0.239
Skin Sensitization:	0.93
Carcinogencity:	0.711
Eye Corrosion:	0.974
Eye Irritation:	0.972
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC88877

Natural Product ID:	NPC88877
*Common Name:**	[(1S,2E)-3,7-Dimethyl-1-[(3S)-4-Methylidene-5-Oxooxolan-3-Yl]-5-Oxoocta-2,6-Dienyl] Acetate
IUPAC Name:	[(1S,2E)-3,7-dimethyl-1-[(3S)-4-methylidene-5-oxooxolan-3-yl]-5-oxoocta-2,6-dienyl] acetate
Synonyms:	4-O-Acetylanthecotulide
Standard InCHIKey:	PESOQZBIMLBDHX-IRZHHCKBSA-N
Standard InCHI:	InChI=1S/C17H22O5/c1-10(2)6-14(19)7-11(3)8-16(22-13(5)18)15-9-21-17(20)12(15)4/h6,8,15-16H,4,7,9H2,1-3,5H3/b11-8+/t15-,16+/m1/s1
SMILES:	C/C(=C[C@@H]([C@@H]1COC(=O)C1=C)OC(=O)C)/CC(=O)C=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496445
PubChem CID:	11522381
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene 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
NPO20111	Anthemis auriculata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643047]
NPO20111	Anthemis auriculata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO20111	Anthemis auriculata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	11

Activity Type	# Activity
Organism	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	81700.0	nM	PMID[482279]
NPT172	Organism	Proteus mirabilis	Proteus mirabilis	MIC	=	163400.0	nM	PMID[482279]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	MIC	=	81700.0	nM	PMID[482279]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	163400.0	nM	PMID[482279]
NPT3729	Organism	Pseudomonas tolaasii	Pseudomonas tolaasii	MIC	=	163400.0	nM	PMID[482279]
NPT3608	Organism	Salmonella enteritidis	Salmonella enterica subsp. enterica serovar Enteritidis	MIC	=	163400.0	nM	PMID[482279]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	81700.0	nM	PMID[482279]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	81700.0	nM	PMID[482279]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	40800.0	nM	PMID[482279]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	81700.0	nM	PMID[482279]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	81700.0	nM	PMID[482279]

☑ 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 NPC88877 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	174
0.1-0.2	1893
0.2-0.3	8642
0.3-0.4	16973
0.4-0.5	8236
0.5-0.6	4897
0.6-0.7	1480
0.7-0.8	354
0.8-0.85	35
0.85-0.9	5
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476591
0.9242	High Similarity	NPC470256
0.913	High Similarity	NPC114727
0.913	High Similarity	NPC476590
0.9091	High Similarity	NPC194871
0.9062	High Similarity	NPC474658
0.8767	High Similarity	NPC270126
0.8615	High Similarity	NPC151648
0.8592	High Similarity	NPC476355
0.8493	Intermediate Similarity	NPC141789
0.8493	Intermediate Similarity	NPC171204
0.8493	Intermediate Similarity	NPC97516
0.8493	Intermediate Similarity	NPC476028
0.84	Intermediate Similarity	NPC281132
0.8382	Intermediate Similarity	NPC248125
0.8356	Intermediate Similarity	NPC123360
0.8356	Intermediate Similarity	NPC68819
0.8333	Intermediate Similarity	NPC259599
0.8333	Intermediate Similarity	NPC140287
0.8333	Intermediate Similarity	NPC294434
0.8333	Intermediate Similarity	NPC117746
0.8333	Intermediate Similarity	NPC15499
0.831	Intermediate Similarity	NPC163003
0.8289	Intermediate Similarity	NPC301477
0.8289	Intermediate Similarity	NPC281949
0.8289	Intermediate Similarity	NPC25684
0.8267	Intermediate Similarity	NPC178277
0.8261	Intermediate Similarity	NPC203335
0.8133	Intermediate Similarity	NPC93763
0.8133	Intermediate Similarity	NPC108816
0.8082	Intermediate Similarity	NPC474758
0.8077	Intermediate Similarity	NPC40746
0.8077	Intermediate Similarity	NPC169575
0.8077	Intermediate Similarity	NPC116543
0.8052	Intermediate Similarity	NPC141810
0.8052	Intermediate Similarity	NPC471325
0.8	Intermediate Similarity	NPC10572
0.8	Intermediate Similarity	NPC57744
0.8	Intermediate Similarity	NPC107787
0.7975	Intermediate Similarity	NPC115786
0.7949	Intermediate Similarity	NPC173609
0.7945	Intermediate Similarity	NPC58956
0.7945	Intermediate Similarity	NPC269206
0.7945	Intermediate Similarity	NPC295633
0.791	Intermediate Similarity	NPC79756
0.7895	Intermediate Similarity	NPC128276
0.7875	Intermediate Similarity	NPC78089
0.7875	Intermediate Similarity	NPC470755
0.7848	Intermediate Similarity	NPC131669
0.7848	Intermediate Similarity	NPC473390
0.7848	Intermediate Similarity	NPC59097
0.7821	Intermediate Similarity	NPC24417
0.7792	Intermediate Similarity	NPC99651
0.7792	Intermediate Similarity	NPC617
0.7792	Intermediate Similarity	NPC98557
0.7792	Intermediate Similarity	NPC167881
0.7778	Intermediate Similarity	NPC475461
0.7778	Intermediate Similarity	NPC305475
0.7763	Intermediate Similarity	NPC41780
0.7763	Intermediate Similarity	NPC7563
0.7763	Intermediate Similarity	NPC470240
0.7763	Intermediate Similarity	NPC187568
0.7763	Intermediate Similarity	NPC476794
0.7763	Intermediate Similarity	NPC116177
0.7763	Intermediate Similarity	NPC320630
0.7763	Intermediate Similarity	NPC65603
0.775	Intermediate Similarity	NPC96259
0.775	Intermediate Similarity	NPC141193
0.775	Intermediate Similarity	NPC476804
0.775	Intermediate Similarity	NPC158756
0.7733	Intermediate Similarity	NPC155587
0.7733	Intermediate Similarity	NPC329852
0.7733	Intermediate Similarity	NPC193351
0.7733	Intermediate Similarity	NPC226669
0.7733	Intermediate Similarity	NPC138408
0.7722	Intermediate Similarity	NPC229825
0.7714	Intermediate Similarity	NPC470688
0.7703	Intermediate Similarity	NPC287878
0.7681	Intermediate Similarity	NPC68110
0.7681	Intermediate Similarity	NPC474774
0.7662	Intermediate Similarity	NPC267231
0.7654	Intermediate Similarity	NPC165162
0.7654	Intermediate Similarity	NPC255307
0.7632	Intermediate Similarity	NPC235906
0.7625	Intermediate Similarity	NPC474703
0.7625	Intermediate Similarity	NPC318468
0.7625	Intermediate Similarity	NPC475947
0.7625	Intermediate Similarity	NPC170286
0.7619	Intermediate Similarity	NPC144133
0.7619	Intermediate Similarity	NPC179394
0.7595	Intermediate Similarity	NPC275507
0.7595	Intermediate Similarity	NPC42470
0.759	Intermediate Similarity	NPC476805
0.759	Intermediate Similarity	NPC475819
0.7564	Intermediate Similarity	NPC264227
0.7564	Intermediate Similarity	NPC63649
0.7564	Intermediate Similarity	NPC473980
0.7564	Intermediate Similarity	NPC471299
0.7564	Intermediate Similarity	NPC472965
0.7564	Intermediate Similarity	NPC473981
0.7561	Intermediate Similarity	NPC150755
0.7561	Intermediate Similarity	NPC50637
0.7561	Intermediate Similarity	NPC469910
0.7534	Intermediate Similarity	NPC476059
0.7534	Intermediate Similarity	NPC473603
0.7532	Intermediate Similarity	NPC474760
0.7531	Intermediate Similarity	NPC159635
0.7531	Intermediate Similarity	NPC163615
0.7531	Intermediate Similarity	NPC191476
0.7531	Intermediate Similarity	NPC38569
0.7531	Intermediate Similarity	NPC114979
0.75	Intermediate Similarity	NPC478194
0.75	Intermediate Similarity	NPC478192
0.75	Intermediate Similarity	NPC166919
0.75	Intermediate Similarity	NPC11383
0.75	Intermediate Similarity	NPC478195
0.75	Intermediate Similarity	NPC475046
0.75	Intermediate Similarity	NPC310450
0.75	Intermediate Similarity	NPC474959
0.75	Intermediate Similarity	NPC475690
0.75	Intermediate Similarity	NPC21998
0.75	Intermediate Similarity	NPC478191
0.75	Intermediate Similarity	NPC478193
0.75	Intermediate Similarity	NPC478196
0.75	Intermediate Similarity	NPC26624
0.747	Intermediate Similarity	NPC266957
0.7468	Intermediate Similarity	NPC223904
0.7468	Intermediate Similarity	NPC302426
0.7465	Intermediate Similarity	NPC282760
0.7442	Intermediate Similarity	NPC288240
0.7442	Intermediate Similarity	NPC295204
0.7442	Intermediate Similarity	NPC165383
0.7442	Intermediate Similarity	NPC162205
0.7442	Intermediate Similarity	NPC273579
0.7439	Intermediate Similarity	NPC215364
0.7439	Intermediate Similarity	NPC155873
0.7436	Intermediate Similarity	NPC475699
0.7436	Intermediate Similarity	NPC471465
0.7436	Intermediate Similarity	NPC196653
0.7432	Intermediate Similarity	NPC469660
0.7432	Intermediate Similarity	NPC202011
0.7412	Intermediate Similarity	NPC129419
0.7412	Intermediate Similarity	NPC475855
0.7412	Intermediate Similarity	NPC473619
0.7407	Intermediate Similarity	NPC284472
0.7407	Intermediate Similarity	NPC229799
0.7407	Intermediate Similarity	NPC286770
0.7397	Intermediate Similarity	NPC218477
0.7381	Intermediate Similarity	NPC475902
0.7381	Intermediate Similarity	NPC476803
0.7381	Intermediate Similarity	NPC287089
0.7375	Intermediate Similarity	NPC255580
0.7375	Intermediate Similarity	NPC39411
0.7375	Intermediate Similarity	NPC52861
0.7349	Intermediate Similarity	NPC279859
0.7349	Intermediate Similarity	NPC469483
0.7349	Intermediate Similarity	NPC38576
0.7349	Intermediate Similarity	NPC284902
0.7333	Intermediate Similarity	NPC84038
0.7333	Intermediate Similarity	NPC129665
0.7333	Intermediate Similarity	NPC316185
0.7326	Intermediate Similarity	NPC123177
0.7326	Intermediate Similarity	NPC74103
0.7326	Intermediate Similarity	NPC473321
0.7326	Intermediate Similarity	NPC150978
0.7326	Intermediate Similarity	NPC70595
0.7326	Intermediate Similarity	NPC284185
0.7324	Intermediate Similarity	NPC148233
0.7324	Intermediate Similarity	NPC25747
0.7317	Intermediate Similarity	NPC41856
0.7308	Intermediate Similarity	NPC68156
0.7297	Intermediate Similarity	NPC151481
0.7297	Intermediate Similarity	NPC475982
0.7297	Intermediate Similarity	NPC470693
0.7294	Intermediate Similarity	NPC268298
0.7284	Intermediate Similarity	NPC89555
0.7284	Intermediate Similarity	NPC35556
0.7273	Intermediate Similarity	NPC161038
0.7273	Intermediate Similarity	NPC244166
0.7262	Intermediate Similarity	NPC231889
0.7262	Intermediate Similarity	NPC473248
0.7262	Intermediate Similarity	NPC160138
0.7262	Intermediate Similarity	NPC475703
0.726	Intermediate Similarity	NPC472266
0.725	Intermediate Similarity	NPC69271
0.725	Intermediate Similarity	NPC74673
0.7246	Intermediate Similarity	NPC286189
0.7241	Intermediate Similarity	NPC475302
0.7241	Intermediate Similarity	NPC125674
0.7241	Intermediate Similarity	NPC228451
0.7241	Intermediate Similarity	NPC469692
0.7241	Intermediate Similarity	NPC475838
0.7241	Intermediate Similarity	NPC469645
0.7237	Intermediate Similarity	NPC16349
0.7237	Intermediate Similarity	NPC222244
0.7237	Intermediate Similarity	NPC474705
0.7237	Intermediate Similarity	NPC284006
0.7229	Intermediate Similarity	NPC21469
0.7222	Intermediate Similarity	NPC470123
0.7222	Intermediate Similarity	NPC131174

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 NPC88877 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	2467
0.2-0.3	4323
0.3-0.4	1610
0.4-0.5	419
0.5-0.6	134
0.6-0.7	37
0.7-0.8	0
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
0.7284	Intermediate Similarity	NPD5209	Approved
0.7077	Intermediate Similarity	NPD6927	Phase 3
0.6986	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1694	Approved
0.6824	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1695	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5785	Approved
0.6629	Remote Similarity	NPD6698	Approved
0.6629	Remote Similarity	NPD46	Approved
0.6627	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4225	Approved
0.6444	Remote Similarity	NPD7838	Discovery
0.6437	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD5363	Approved
0.6395	Remote Similarity	NPD7154	Phase 3
0.6386	Remote Similarity	NPD4271	Approved
0.6386	Remote Similarity	NPD4268	Approved
0.6364	Remote Similarity	NPD5343	Approved
0.6364	Remote Similarity	NPD4249	Approved
0.6364	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4251	Approved
0.6292	Remote Similarity	NPD4250	Approved
0.6235	Remote Similarity	NPD4822	Approved
0.6235	Remote Similarity	NPD4821	Approved
0.6235	Remote Similarity	NPD4819	Approved
0.6235	Remote Similarity	NPD4252	Approved
0.6235	Remote Similarity	NPD4820	Approved
0.6176	Remote Similarity	NPD6371	Approved
0.6146	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD4270	Approved
0.6092	Remote Similarity	NPD6435	Approved
0.6092	Remote Similarity	NPD4269	Approved
0.6071	Remote Similarity	NPD4756	Discovery
0.6027	Remote Similarity	NPD8779	Phase 3
0.6024	Remote Similarity	NPD8039	Approved
0.6024	Remote Similarity	NPD1452	Discontinued
0.6023	Remote Similarity	NPD5362	Discontinued
0.6	Remote Similarity	NPD5786	Approved
0.6	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD5369	Approved
0.5909	Remote Similarity	NPD6096	Approved
0.5909	Remote Similarity	NPD6097	Approved
0.5895	Remote Similarity	NPD5282	Discontinued
0.5862	Remote Similarity	NPD5368	Approved
0.5851	Remote Similarity	NPD7983	Approved
0.5843	Remote Similarity	NPD6110	Phase 1
0.5843	Remote Similarity	NPD5331	Approved
0.5843	Remote Similarity	NPD5332	Approved
0.5825	Remote Similarity	NPD6686	Approved
0.5824	Remote Similarity	NPD7146	Approved
0.5824	Remote Similarity	NPD6409	Approved
0.5824	Remote Similarity	NPD7521	Approved
0.5824	Remote Similarity	NPD6684	Approved
0.5824	Remote Similarity	NPD5330	Approved
0.5824	Remote Similarity	NPD7334	Approved
0.5816	Remote Similarity	NPD7638	Approved
0.5806	Remote Similarity	NPD5370	Suspended
0.5795	Remote Similarity	NPD4790	Discontinued
0.5789	Remote Similarity	NPD6399	Phase 3
0.5789	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD7640	Approved
0.5758	Remote Similarity	NPD6648	Approved
0.5758	Remote Similarity	NPD7639	Approved
0.575	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5733	Remote Similarity	NPD69	Approved
0.5733	Remote Similarity	NPD9119	Approved
0.5733	Remote Similarity	NPD6109	Phase 1
0.5729	Remote Similarity	NPD7900	Approved
0.5729	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.57	Remote Similarity	NPD5344	Discontinued
0.5699	Remote Similarity	NPD6903	Approved
0.5699	Remote Similarity	NPD6672	Approved
0.5699	Remote Similarity	NPD5737	Approved
0.5699	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD7115	Discovery
0.5684	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD5693	Phase 1
0.5684	Remote Similarity	NPD7637	Suspended
0.566	Remote Similarity	NPD2204	Approved
0.566	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD6008	Approved
0.5625	Remote Similarity	NPD5779	Approved
0.5625	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5778	Approved
0.5616	Remote Similarity	NPD9298	Approved
0.5607	Remote Similarity	NPD6053	Discontinued
0.56	Remote Similarity	NPD9118	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