NPASS Compound

Structure

NPC474860 OpenBabel07101718322D 29 30 0 0 1 0 0 0 0 0999 V2000 3.0981 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -7.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4282 -4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.6728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -5.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1603 -4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -4.0388 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 3.0981 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -5.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1603 -5.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.4282 -4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0263 -6.0388 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 -1.2601 -1.2601 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 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 10 17 2 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 0 0 0 0 15 25 1 0 0 0 0 16 20 2 0 0 0 0 16 23 1 0 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 20 24 1 0 0 0 0 21 25 1 0 0 0 0 22 26 2 0 0 0 0 23 27 2 0 0 0 0 23 29 1 0 0 0 0 24 28 1 0 0 0 0 24 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.26
Volume:	443.185
LogP:	5.356
LogD:	4.359
LogS:	-4.222
# Rotatable Bonds:	8
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.48
Synthetic Accessibility Score:	4.271
Fsp3:	0.56
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.966
MDCK Permeability:	2.354872049181722e-05
Pgp-inhibitor:	0.093
Pgp-substrate:	0.041
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.761
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	94.88314056396484%
Volume Distribution (VD):	1.325
Pgp-substrate:	0.8600450158119202%

ADMET: Metabolism

CYP1A2-inhibitor:	0.101
CYP1A2-substrate:	0.411
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.493
CYP2C9-substrate:	0.975
CYP2D6-inhibitor:	0.565
CYP2D6-substrate:	0.892
CYP3A4-inhibitor:	0.144
CYP3A4-substrate:	0.157

ADMET: Excretion

Clearance (CL):	4.771
Half-life (T1/2):	0.683

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.19
Drug-inuced Liver Injury (DILI):	0.058
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.129
Maximum Recommended Daily Dose:	0.088
Skin Sensitization:	0.156
Carcinogencity:	0.35
Eye Corrosion:	0.01
Eye Irritation:	0.198
Respiratory Toxicity:	0.912

Download Data

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

Natural Product: NPC474860

Natural Product ID:	NPC474860
*Common Name:**	Acantholide B
IUPAC Name:	3-[(3E,7E)-4,8-dimethyl-10-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)deca-3,7-dienyl]-2-hydroxy-2H-furan-5-one
Synonyms:
Standard InCHIKey:	XPWNPMMYRFJXQW-SCNFBCNRSA-N
Standard InCHI:	InChI=1S/C25H36O4/c1-17(10-7-11-20-16-23(27)29-24(20)28)8-6-9-18(2)12-13-21-19(3)22(26)14-15-25(21,4)5/h9-10,16,24,28H,6-8,11-15H2,1-5H3/b17-10+,18-9+
SMILES:	CC1=C(C(CCC1=O)(C)C)CCC(=CCCC(=CCCC2=CC(=O)OC2O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485661
PubChem CID:	11223324
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
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510593]
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	Indonesia	n.a.	PMID[15568767]
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18257533]
NPO33221	hyrtios communis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23944963]
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834155]

☑ 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	1
IC50	2
Others	5

Activity Type	# Activity
Cell Line	3
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	ED50	>	10.0	ug ml-1	PMID[567402]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[567403]
NPT396	Cell Line	T47D	Homo sapiens	IC50	>	10000.0	nM	PMID[567403]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	10.0	mm	PMID[567402]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	12.0	mm	PMID[567402]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	9.0	mm	PMID[567402]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	10.0	mm	PMID[567402]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	IZ	=	10.0	mm	PMID[567402]

☑ 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 NPC474860 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	178
0.1-0.2	1146
0.2-0.3	5641
0.3-0.4	14187
0.4-0.5	10614
0.5-0.6	7024
0.6-0.7	3506
0.7-0.8	357
0.8-0.85	26
0.85-0.9	14
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471300
0.962	High Similarity	NPC471296
0.9146	High Similarity	NPC31086
0.8987	High Similarity	NPC473756
0.8902	High Similarity	NPC323251
0.8902	High Similarity	NPC471298
0.8795	High Similarity	NPC471297
0.869	High Similarity	NPC471301
0.869	High Similarity	NPC126518
0.8675	High Similarity	NPC324170
0.8625	High Similarity	NPC27205
0.8588	High Similarity	NPC163606
0.8539	High Similarity	NPC242069
0.8537	High Similarity	NPC471299
0.8523	High Similarity	NPC232426
0.8523	High Similarity	NPC477782
0.8523	High Similarity	NPC281942
0.8488	Intermediate Similarity	NPC211892
0.8471	Intermediate Similarity	NPC471302
0.8471	Intermediate Similarity	NPC474865
0.8427	Intermediate Similarity	NPC477783
0.8427	Intermediate Similarity	NPC141831
0.8415	Intermediate Similarity	NPC209135
0.8415	Intermediate Similarity	NPC474816
0.8352	Intermediate Similarity	NPC476488
0.8352	Intermediate Similarity	NPC476487
0.8333	Intermediate Similarity	NPC469939
0.8293	Intermediate Similarity	NPC262747
0.825	Intermediate Similarity	NPC476489
0.825	Intermediate Similarity	NPC476490
0.8202	Intermediate Similarity	NPC251528
0.8202	Intermediate Similarity	NPC5509
0.8193	Intermediate Similarity	NPC471220
0.8182	Intermediate Similarity	NPC312561
0.8182	Intermediate Similarity	NPC475678
0.8172	Intermediate Similarity	NPC475709
0.8125	Intermediate Similarity	NPC257618
0.8118	Intermediate Similarity	NPC475944
0.809	Intermediate Similarity	NPC474629
0.8068	Intermediate Similarity	NPC474062
0.8065	Intermediate Similarity	NPC470801
0.8043	Intermediate Similarity	NPC475572
0.8043	Intermediate Similarity	NPC474554
0.8	Intermediate Similarity	NPC477720
0.8	Intermediate Similarity	NPC470734
0.7979	Intermediate Similarity	NPC53844
0.7955	Intermediate Similarity	NPC473251
0.7955	Intermediate Similarity	NPC42586
0.7931	Intermediate Similarity	NPC474809
0.7912	Intermediate Similarity	NPC51486
0.7889	Intermediate Similarity	NPC472809
0.7889	Intermediate Similarity	NPC472810
0.7889	Intermediate Similarity	NPC196407
0.7872	Intermediate Similarity	NPC240673
0.7872	Intermediate Similarity	NPC17578
0.7849	Intermediate Similarity	NPC474555
0.7849	Intermediate Similarity	NPC53685
0.7849	Intermediate Similarity	NPC104925
0.7849	Intermediate Similarity	NPC298973
0.7826	Intermediate Similarity	NPC179517
0.7826	Intermediate Similarity	NPC477122
0.7826	Intermediate Similarity	NPC165904
0.7812	Intermediate Similarity	NPC472644
0.7805	Intermediate Similarity	NPC16349
0.7805	Intermediate Similarity	NPC222244
0.7802	Intermediate Similarity	NPC174342
0.7789	Intermediate Similarity	NPC208094
0.7789	Intermediate Similarity	NPC476253
0.7778	Intermediate Similarity	NPC153095
0.7753	Intermediate Similarity	NPC65661
0.7753	Intermediate Similarity	NPC189311
0.7753	Intermediate Similarity	NPC86316
0.7753	Intermediate Similarity	NPC106416
0.7742	Intermediate Similarity	NPC166346
0.7742	Intermediate Similarity	NPC472303
0.7742	Intermediate Similarity	NPC115021
0.7732	Intermediate Similarity	NPC472643
0.7732	Intermediate Similarity	NPC63249
0.7732	Intermediate Similarity	NPC471075
0.7727	Intermediate Similarity	NPC193198
0.7692	Intermediate Similarity	NPC472378
0.7667	Intermediate Similarity	NPC315395
0.7667	Intermediate Similarity	NPC316426
0.766	Intermediate Similarity	NPC469697
0.7653	Intermediate Similarity	NPC134077
0.764	Intermediate Similarity	NPC71626
0.764	Intermediate Similarity	NPC470800
0.764	Intermediate Similarity	NPC149869
0.7634	Intermediate Similarity	NPC472811
0.7634	Intermediate Similarity	NPC289479
0.7634	Intermediate Similarity	NPC472814
0.7634	Intermediate Similarity	NPC177037
0.7629	Intermediate Similarity	NPC476767
0.7604	Intermediate Similarity	NPC253826
0.7586	Intermediate Similarity	NPC160582
0.7579	Intermediate Similarity	NPC295347
0.7579	Intermediate Similarity	NPC209355
0.7579	Intermediate Similarity	NPC473369
0.7556	Intermediate Similarity	NPC472442
0.7556	Intermediate Similarity	NPC217394
0.7556	Intermediate Similarity	NPC474424
0.7556	Intermediate Similarity	NPC329630
0.7553	Intermediate Similarity	NPC472812
0.7553	Intermediate Similarity	NPC139692
0.7528	Intermediate Similarity	NPC16488
0.7528	Intermediate Similarity	NPC42476
0.7528	Intermediate Similarity	NPC472440
0.7527	Intermediate Similarity	NPC477149
0.7527	Intermediate Similarity	NPC477147
0.7527	Intermediate Similarity	NPC475879
0.75	Intermediate Similarity	NPC134072
0.75	Intermediate Similarity	NPC229584
0.75	Intermediate Similarity	NPC234993
0.75	Intermediate Similarity	NPC162346
0.75	Intermediate Similarity	NPC242848
0.75	Intermediate Similarity	NPC143446
0.75	Intermediate Similarity	NPC40228
0.75	Intermediate Similarity	NPC475739
0.75	Intermediate Similarity	NPC202833
0.75	Intermediate Similarity	NPC14203
0.7474	Intermediate Similarity	NPC324078
0.7474	Intermediate Similarity	NPC476415
0.7474	Intermediate Similarity	NPC470255
0.7473	Intermediate Similarity	NPC261721
0.7473	Intermediate Similarity	NPC220478
0.7471	Intermediate Similarity	NPC321728
0.7471	Intermediate Similarity	NPC150646
0.7451	Intermediate Similarity	NPC476765
0.7451	Intermediate Similarity	NPC392
0.7451	Intermediate Similarity	NPC177524
0.7451	Intermediate Similarity	NPC219900
0.7449	Intermediate Similarity	NPC54705
0.7449	Intermediate Similarity	NPC469864
0.7449	Intermediate Similarity	NPC469872
0.7447	Intermediate Similarity	NPC65513
0.7447	Intermediate Similarity	NPC472705
0.7444	Intermediate Similarity	NPC475100
0.7444	Intermediate Similarity	NPC474359
0.7426	Intermediate Similarity	NPC472645
0.7423	Intermediate Similarity	NPC474343
0.7423	Intermediate Similarity	NPC76266
0.7423	Intermediate Similarity	NPC477719
0.7423	Intermediate Similarity	NPC69385
0.7423	Intermediate Similarity	NPC477718
0.7419	Intermediate Similarity	NPC168131
0.7419	Intermediate Similarity	NPC214387
0.7416	Intermediate Similarity	NPC200513
0.7416	Intermediate Similarity	NPC268122
0.7412	Intermediate Similarity	NPC228978
0.7412	Intermediate Similarity	NPC65650
0.7396	Intermediate Similarity	NPC472441
0.7391	Intermediate Similarity	NPC45409
0.7379	Intermediate Similarity	NPC476759
0.7374	Intermediate Similarity	NPC303559
0.7368	Intermediate Similarity	NPC471571
0.7368	Intermediate Similarity	NPC476597
0.7368	Intermediate Similarity	NPC476416
0.7368	Intermediate Similarity	NPC476598
0.7363	Intermediate Similarity	NPC30984
0.7363	Intermediate Similarity	NPC261380
0.7356	Intermediate Similarity	NPC192006
0.7356	Intermediate Similarity	NPC128276
0.7356	Intermediate Similarity	NPC475994
0.7356	Intermediate Similarity	NPC93763
0.7356	Intermediate Similarity	NPC108816
0.7349	Intermediate Similarity	NPC67183
0.7347	Intermediate Similarity	NPC222011
0.7347	Intermediate Similarity	NPC473154
0.734	Intermediate Similarity	NPC473455
0.734	Intermediate Similarity	NPC145666
0.734	Intermediate Similarity	NPC476437
0.734	Intermediate Similarity	NPC476369
0.734	Intermediate Similarity	NPC166554
0.734	Intermediate Similarity	NPC471818
0.734	Intermediate Similarity	NPC473448
0.7333	Intermediate Similarity	NPC311070
0.7333	Intermediate Similarity	NPC472377
0.7333	Intermediate Similarity	NPC118423
0.7333	Intermediate Similarity	NPC161045
0.732	Intermediate Similarity	NPC319692
0.732	Intermediate Similarity	NPC325960
0.732	Intermediate Similarity	NPC112654
0.7312	Intermediate Similarity	NPC226863
0.7308	Intermediate Similarity	NPC476766
0.7303	Intermediate Similarity	NPC325031
0.7303	Intermediate Similarity	NPC471325
0.73	Intermediate Similarity	NPC223834
0.73	Intermediate Similarity	NPC476769
0.7292	Intermediate Similarity	NPC2003
0.7292	Intermediate Similarity	NPC96541
0.7292	Intermediate Similarity	NPC25701
0.7292	Intermediate Similarity	NPC476596
0.7283	Intermediate Similarity	NPC322159
0.7283	Intermediate Similarity	NPC202394
0.7283	Intermediate Similarity	NPC168248
0.7283	Intermediate Similarity	NPC305475
0.7283	Intermediate Similarity	NPC469483
0.7283	Intermediate Similarity	NPC475461
0.7282	Intermediate Similarity	NPC90946
0.7282	Intermediate Similarity	NPC325054

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 NPC474860 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1727
0.2-0.3	4059
0.3-0.4	2241
0.4-0.5	610
0.5-0.6	297
0.6-0.7	63
0.7-0.8	4
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.869	High Similarity	NPD6400	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6686	Approved
0.7416	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD8039	Approved
0.7356	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD5785	Approved
0.6979	Remote Similarity	NPD6698	Approved
0.6979	Remote Similarity	NPD46	Approved
0.6957	Remote Similarity	NPD7154	Phase 3
0.6931	Remote Similarity	NPD7640	Approved
0.6931	Remote Similarity	NPD7639	Approved
0.69	Remote Similarity	NPD6083	Phase 2
0.69	Remote Similarity	NPD6084	Phase 2
0.6832	Remote Similarity	NPD7638	Approved
0.6829	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5363	Approved
0.6809	Remote Similarity	NPD1694	Approved
0.6774	Remote Similarity	NPD5362	Discontinued
0.6771	Remote Similarity	NPD6672	Approved
0.6771	Remote Similarity	NPD5737	Approved
0.6768	Remote Similarity	NPD7748	Approved
0.6737	Remote Similarity	NPD5330	Approved
0.6737	Remote Similarity	NPD7146	Approved
0.6737	Remote Similarity	NPD7521	Approved
0.6737	Remote Similarity	NPD6684	Approved
0.6737	Remote Similarity	NPD7334	Approved
0.6737	Remote Similarity	NPD6409	Approved
0.6735	Remote Similarity	NPD7515	Phase 2
0.67	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5695	Phase 3
0.6698	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD7331	Phase 2
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD4756	Discovery
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.663	Remote Similarity	NPD4252	Approved
0.6607	Remote Similarity	NPD7115	Discovery
0.6598	Remote Similarity	NPD6903	Approved
0.6598	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4193	Approved
0.6585	Remote Similarity	NPD4194	Approved
0.6585	Remote Similarity	NPD4192	Approved
0.6585	Remote Similarity	NPD4191	Approved
0.6569	Remote Similarity	NPD7902	Approved
0.6566	Remote Similarity	NPD7637	Suspended
0.6566	Remote Similarity	NPD6411	Approved
0.6566	Remote Similarity	NPD5693	Phase 1
0.6562	Remote Similarity	NPD5786	Approved
0.6548	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD3665	Phase 1
0.6526	Remote Similarity	NPD3133	Approved
0.6526	Remote Similarity	NPD3666	Approved
0.6514	Remote Similarity	NPD6371	Approved
0.6505	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5696	Approved
0.6489	Remote Similarity	NPD6435	Approved
0.6471	Remote Similarity	NPD7839	Suspended
0.6458	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6675	Approved
0.6449	Remote Similarity	NPD6402	Approved
0.6449	Remote Similarity	NPD7128	Approved
0.6449	Remote Similarity	NPD5739	Approved
0.6441	Remote Similarity	NPD7507	Approved
0.6396	Remote Similarity	NPD6882	Approved
0.6392	Remote Similarity	NPD4623	Approved
0.6392	Remote Similarity	NPD5279	Phase 3
0.6392	Remote Similarity	NPD4519	Discontinued
0.6392	Remote Similarity	NPD3618	Phase 1
0.6383	Remote Similarity	NPD5369	Approved
0.6364	Remote Similarity	NPD6080	Approved
0.6364	Remote Similarity	NPD4753	Phase 2
0.6364	Remote Similarity	NPD5328	Approved
0.6364	Remote Similarity	NPD6673	Approved
0.6364	Remote Similarity	NPD6904	Approved
0.6364	Remote Similarity	NPD6101	Approved
0.6364	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4786	Approved
0.633	Remote Similarity	NPD7320	Approved
0.633	Remote Similarity	NPD6899	Approved
0.633	Remote Similarity	NPD6881	Approved
0.6321	Remote Similarity	NPD7632	Discontinued
0.6316	Remote Similarity	NPD3667	Approved
0.6289	Remote Similarity	NPD1696	Phase 3
0.6281	Remote Similarity	NPD7319	Approved
0.6277	Remote Similarity	NPD4819	Approved
0.6277	Remote Similarity	NPD4821	Approved
0.6277	Remote Similarity	NPD4822	Approved
0.6277	Remote Similarity	NPD4820	Approved
0.6277	Remote Similarity	NPD4695	Discontinued
0.6277	Remote Similarity	NPD5368	Approved
0.6275	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7900	Approved
0.6273	Remote Similarity	NPD6373	Approved
0.6273	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6372	Approved
0.625	Remote Similarity	NPD5332	Approved
0.625	Remote Similarity	NPD5331	Approved
0.625	Remote Similarity	NPD6053	Discontinued
0.6239	Remote Similarity	NPD5701	Approved
0.6239	Remote Similarity	NPD5697	Approved
0.6238	Remote Similarity	NPD7983	Approved
0.6238	Remote Similarity	NPD6079	Approved
0.6238	Remote Similarity	NPD6050	Approved
0.6238	Remote Similarity	NPD5284	Approved
0.6238	Remote Similarity	NPD5281	Approved
0.6237	Remote Similarity	NPD4271	Approved
0.6237	Remote Similarity	NPD4268	Approved
0.6216	Remote Similarity	NPD6883	Approved
0.6216	Remote Similarity	NPD7102	Approved
0.6216	Remote Similarity	NPD7290	Approved
0.6214	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4790	Discontinued
0.62	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6011	Approved
0.6163	Remote Similarity	NPD7341	Phase 2
0.6161	Remote Similarity	NPD6650	Approved
0.6161	Remote Similarity	NPD6617	Approved
0.6161	Remote Similarity	NPD6649	Approved
0.6161	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD6847	Approved
0.6161	Remote Similarity	NPD6869	Approved
0.6161	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD8130	Phase 1
0.6146	Remote Similarity	NPD4223	Phase 3
0.6146	Remote Similarity	NPD4221	Approved
0.6139	Remote Similarity	NPD7838	Discovery
0.6139	Remote Similarity	NPD5692	Phase 3
0.6126	Remote Similarity	NPD6014	Approved
0.6126	Remote Similarity	NPD6012	Approved
0.6126	Remote Similarity	NPD6013	Approved
0.6122	Remote Similarity	NPD5329	Approved
0.6121	Remote Similarity	NPD7327	Approved
0.6121	Remote Similarity	NPD7328	Approved
0.6106	Remote Similarity	NPD8297	Approved
0.6102	Remote Similarity	NPD8513	Phase 3
0.6102	Remote Similarity	NPD8515	Approved
0.6102	Remote Similarity	NPD8517	Approved
0.6102	Remote Similarity	NPD8516	Approved
0.61	Remote Similarity	NPD5208	Approved
0.6092	Remote Similarity	NPD3704	Approved
0.6082	Remote Similarity	NPD6110	Phase 1
0.6078	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5694	Approved
0.6071	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD7516	Approved
0.6067	Remote Similarity	NPD4137	Phase 3
0.6061	Remote Similarity	NPD6098	Approved
0.6058	Remote Similarity	NPD5210	Approved
0.6058	Remote Similarity	NPD4629	Approved
0.604	Remote Similarity	NPD6051	Approved
0.604	Remote Similarity	NPD5370	Suspended
0.602	Remote Similarity	NPD4197	Approved
0.6019	Remote Similarity	NPD4202	Approved
0.6019	Remote Similarity	NPD5211	Phase 2
0.6017	Remote Similarity	NPD8294	Approved
0.6017	Remote Similarity	NPD8377	Approved
0.6	Remote Similarity	NPD4691	Approved
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD3573	Approved
0.6	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4250	Approved
0.6	Remote Similarity	NPD4747	Approved
0.6	Remote Similarity	NPD8328	Phase 3
0.6	Remote Similarity	NPD5221	Approved
0.6	Remote Similarity	NPD4251	Approved
0.5984	Remote Similarity	NPD8293	Discontinued
0.5982	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD6404	Discontinued
0.598	Remote Similarity	NPD5207	Approved
0.5978	Remote Similarity	NPD5733	Approved
0.5976	Remote Similarity	NPD4219	Approved
0.5968	Remote Similarity	NPD6914	Discontinued
0.5966	Remote Similarity	NPD8380	Approved
0.5966	Remote Similarity	NPD8335	Approved
0.5966	Remote Similarity	NPD7503	Approved
0.5966	Remote Similarity	NPD8379	Approved
0.5966	Remote Similarity	NPD8033	Approved
0.5966	Remote Similarity	NPD8378	Approved
0.5966	Remote Similarity	NPD8296	Approved
0.5963	Remote Similarity	NPD6647	Phase 2
0.5962	Remote Similarity	NPD5282	Discontinued
0.5949	Remote Similarity	NPD6927	Phase 3
0.5948	Remote Similarity	NPD6868	Approved
0.5946	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD4755	Approved
0.5943	Remote Similarity	NPD5173	Approved
0.5935	Remote Similarity	NPD7736	Approved
0.5934	Remote Similarity	NPD5276	Approved
0.593	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5344	Discontinued

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