NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	840.54
Volume:	915.195
LogP:	2.545
LogD:	2.224
LogS:	-4.07
# Rotatable Bonds:	15
TPSA:	194.21
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	1
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.049
Synthetic Accessibility Score:	6.55
Fsp3:	0.592
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.367
MDCK Permeability:	1.5546742361038923e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.727
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	93.3182373046875%
Volume Distribution (VD):	0.555
Pgp-substrate:	3.4614362716674805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.096
CYP1A2-substrate:	0.044
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.659
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.923
CYP3A4-inhibitor:	0.509
CYP3A4-substrate:	0.049

ADMET: Excretion

Clearance (CL):	1.02
Half-life (T1/2):	0.735

ADMET: Toxicity

hERG Blockers:	0.77
Human Hepatotoxicity (H-HT):	0.977
Drug-inuced Liver Injury (DILI):	0.118
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.596
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.963
Carcinogencity:	0.128
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC477959

Natural Product ID:	NPC477959
*Common Name:**	(4E,6S,8E,10E,12E,14E,16E,18E,20R,21R)-6,20-dihydroxy-5,18-dimethyl-21-[(2S,4R,8S,10Z,12E,15S,16R,17S,18S,19R,20R)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid
IUPAC Name:	(4E,6S,8E,10E,12E,14E,16E,18E,20R,21R)-6,20-dihydroxy-5,18-dimethyl-21-[(2S,4R,8S,10Z,12E,15S,16R,17S,18S,19R,20R)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid
Synonyms:	Etnangien
Standard InCHIKey:	UGSFSPKOZZJEIG-VHNYOPLKSA-N
Standard InCHI:	InChI=1S/C49H76O11/c1-34(23-17-13-11-9-8-10-12-14-20-29-42(51)35(2)25-21-30-46(54)55)31-43(52)37(4)45-32-40(50)26-22-28-41(59-7)27-19-16-15-18-24-36(3)48(57)39(6)49(58)38(5)44(53)33-47(56)60-45/h8-20,23,25,31,36-45,48-53,57-58H,21-22,24,26-30,32-33H2,1-7H3,(H,54,55)/b9-8+,12-10+,13-11+,18-15+,19-16-,20-14+,23-17+,34-31+,35-25+/t36-,37+,38+,39-,40+,41+,42-,43+,44+,45-,48+,49-/m0/s1
SMILES:	C[C@H]1C/C=C/C=C\C[C@H](CCC[C@H](C[C@H](OC(=O)C[C@H]([C@H]([C@@H]([C@H]([C@@H]1O)C)O)C)O)[C@H](C)[C@@H](/C=C(\C)/C=C/C=C/C=C/C=C/C=C/C[C@@H](/C(=C/CCC(=O)O)/C)O)O)O)OC
Synthetic Gene Cluster:	BGC0000179;
ChEMBL Identifier:	n.a.
PubChem CID:	46231262
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002950] Very long-chain fatty acids

*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
NPO13516	Sorangium cellulosum	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14510597]
NPO13516	Sorangium cellulosum	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17547459]
NPO13516	Sorangium cellulosum	Species	Polyangiaceae	Bacteria	culture broth	n.a.	n.a.	PMID[17547459]
NPO13516	Sorangium cellulosum	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[7916271]
NPO13516	Sorangium cellulosum	Species	Polyangiaceae	Bacteria	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
IC50	1
MIC	28
Others	2

Activity Type	# Activity
Cell Line	1
Organism	27
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	IC50	=	74	ug/ml	PMID[17547459]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1	ug/ml	PMID[17547459]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	2	ug/ml	PMID[17547459]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	10	ug/ml	PMID[17547459]
NPT1230	Organism	Bacillus megaterium	Bacillus megaterium	MIC	=	20	ug/ml	PMID[17547459]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	0.06	ug/ml	PMID[17547459]
NPT2	Others	Unspecified		MIC	=	0.12	ug/ml	PMID[17547459]
NPT2	Others	Unspecified		MIC	=	0.06	ug/ml	PMID[17547459]
NPT1382	Organism	Corynebacterium glutamicum	Corynebacterium glutamicum	MIC	=	0.03	ug/ml	PMID[17547459]
NPT1177	Organism	Mycobacterium phlei	Mycobacterium phlei	MIC	=	0.12	ug/ml	PMID[17547459]
NPT4585	Organism	Mycobacterium diernhoferi	Mycobacterium diernhoferi	MIC	=	0.12	ug/ml	PMID[17547459]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	1	ug/ml	PMID[17547459]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	80	ug/ml	PMID[17547459]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	80	ug/ml	PMID[17547459]
NPT3628	Organism	Rhodotorula glutinis	Rhodotorula glutinis	MIC	>	80	ug/ml	PMID[17547459]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	Activity	=	10	%	PMID[17547459]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1	ug/ml	PMID[20045639]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	0.06	ug/ml	PMID[20045639]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	80	ug/ml	PMID[20045639]
NPT1382	Organism	Corynebacterium glutamicum	Corynebacterium glutamicum	MIC	=	0.03	ug/ml	PMID[20045639]
NPT1177	Organism	Mycobacterium phlei	Mycobacterium phlei	MIC	=	0.12	ug/ml	PMID[20045639]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	80	ug/ml	PMID[20045639]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1	ug/ml	PMID[22832317]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	10	ug/ml	PMID[22832317]
NPT1382	Organism	Corynebacterium glutamicum	Corynebacterium glutamicum	MIC	=	0.03	ug/ml	PMID[22832317]
NPT1177	Organism	Mycobacterium phlei	Mycobacterium phlei	MIC	=	0.12	ug/ml	PMID[22832317]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	0.39	ug/ml	PMID[22832317]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	80	ug/ml	PMID[22832317]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	80	ug/ml	PMID[22832317]
NPT2	Others	Unspecified		MIC	=	0.06	ug/ml	PMID[22832317]

☑ 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 NPC477959 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	199
0.1-0.2	1085
0.2-0.3	4328
0.3-0.4	7962
0.4-0.5	16529
0.5-0.6	8411
0.6-0.7	3567
0.7-0.8	585
0.8-0.85	17
0.85-0.9	10
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC313670
0.9518	High Similarity	NPC86005
0.9091	High Similarity	NPC5418
0.8889	High Similarity	NPC165332
0.8889	High Similarity	NPC180722
0.8889	High Similarity	NPC195645
0.8427	Intermediate Similarity	NPC118193
0.8427	Intermediate Similarity	NPC256902
0.8372	Intermediate Similarity	NPC69469
0.8315	Intermediate Similarity	NPC201046
0.8272	Intermediate Similarity	NPC326024
0.814	Intermediate Similarity	NPC315731
0.814	Intermediate Similarity	NPC184208
0.814	Intermediate Similarity	NPC8538
0.8105	Intermediate Similarity	NPC161855
0.809	Intermediate Similarity	NPC316426
0.809	Intermediate Similarity	NPC164393
0.809	Intermediate Similarity	NPC122502
0.809	Intermediate Similarity	NPC315395
0.8085	Intermediate Similarity	NPC473291
0.8043	Intermediate Similarity	NPC472199
0.8022	Intermediate Similarity	NPC97577
0.8	Intermediate Similarity	NPC40812
0.8	Intermediate Similarity	NPC127526
0.7979	Intermediate Similarity	NPC36954
0.7978	Intermediate Similarity	NPC137033
0.7957	Intermediate Similarity	NPC478036
0.7957	Intermediate Similarity	NPC478037
0.7957	Intermediate Similarity	NPC476049
0.7938	Intermediate Similarity	NPC316250
0.7935	Intermediate Similarity	NPC476004
0.7935	Intermediate Similarity	NPC316228
0.7935	Intermediate Similarity	NPC474761
0.7917	Intermediate Similarity	NPC308567
0.7917	Intermediate Similarity	NPC261377
0.7917	Intermediate Similarity	NPC255592
0.7912	Intermediate Similarity	NPC227379
0.7912	Intermediate Similarity	NPC474471
0.7895	Intermediate Similarity	NPC476315
0.7889	Intermediate Similarity	NPC475753
0.7889	Intermediate Similarity	NPC116575
0.7879	Intermediate Similarity	NPC469869
0.7872	Intermediate Similarity	NPC472198
0.7865	Intermediate Similarity	NPC474776
0.7857	Intermediate Similarity	NPC473596
0.7857	Intermediate Similarity	NPC478156
0.7849	Intermediate Similarity	NPC36491
0.7849	Intermediate Similarity	NPC472197
0.7831	Intermediate Similarity	NPC325627
0.7831	Intermediate Similarity	NPC477085
0.7826	Intermediate Similarity	NPC295312
0.7826	Intermediate Similarity	NPC474032
0.7822	Intermediate Similarity	NPC193765
0.7822	Intermediate Similarity	NPC473807
0.7802	Intermediate Similarity	NPC471738
0.7802	Intermediate Similarity	NPC179659
0.78	Intermediate Similarity	NPC476738
0.78	Intermediate Similarity	NPC476740
0.7791	Intermediate Similarity	NPC121200
0.7789	Intermediate Similarity	NPC54905
0.7789	Intermediate Similarity	NPC471142
0.7789	Intermediate Similarity	NPC272050
0.7789	Intermediate Similarity	NPC314009
0.7778	Intermediate Similarity	NPC242233
0.7778	Intermediate Similarity	NPC309398
0.7778	Intermediate Similarity	NPC474581
0.7778	Intermediate Similarity	NPC475367
0.7778	Intermediate Similarity	NPC473816
0.7767	Intermediate Similarity	NPC21713
0.7767	Intermediate Similarity	NPC475608
0.7766	Intermediate Similarity	NPC475912
0.7766	Intermediate Similarity	NPC476300
0.7765	Intermediate Similarity	NPC469880
0.7753	Intermediate Similarity	NPC16488
0.7753	Intermediate Similarity	NPC170377
0.7753	Intermediate Similarity	NPC11620
0.7742	Intermediate Similarity	NPC71533
0.7742	Intermediate Similarity	NPC106510
0.7732	Intermediate Similarity	NPC187761
0.7732	Intermediate Similarity	NPC83895
0.7717	Intermediate Similarity	NPC153805
0.7711	Intermediate Similarity	NPC477087
0.7711	Intermediate Similarity	NPC477086
0.7711	Intermediate Similarity	NPC320119
0.7708	Intermediate Similarity	NPC473859
0.7708	Intermediate Similarity	NPC230800
0.77	Intermediate Similarity	NPC239162
0.7692	Intermediate Similarity	NPC477994
0.7692	Intermediate Similarity	NPC477993
0.7677	Intermediate Similarity	NPC472754
0.7674	Intermediate Similarity	NPC281296
0.7674	Intermediate Similarity	NPC240170
0.7674	Intermediate Similarity	NPC145898
0.7674	Intermediate Similarity	NPC84360
0.7674	Intermediate Similarity	NPC120776
0.7667	Intermediate Similarity	NPC472958
0.7667	Intermediate Similarity	NPC472957
0.766	Intermediate Similarity	NPC184463
0.766	Intermediate Similarity	NPC30515
0.7654	Intermediate Similarity	NPC49863
0.7653	Intermediate Similarity	NPC288876
0.7653	Intermediate Similarity	NPC475053
0.7653	Intermediate Similarity	NPC474718
0.7653	Intermediate Similarity	NPC469871
0.7653	Intermediate Similarity	NPC469870
0.7647	Intermediate Similarity	NPC199445
0.764	Intermediate Similarity	NPC7414
0.7634	Intermediate Similarity	NPC212598
0.7629	Intermediate Similarity	NPC475438
0.7614	Intermediate Similarity	NPC474510
0.7609	Intermediate Similarity	NPC474765
0.7609	Intermediate Similarity	NPC199382
0.7609	Intermediate Similarity	NPC248602
0.7604	Intermediate Similarity	NPC475659
0.7604	Intermediate Similarity	NPC300710
0.7604	Intermediate Similarity	NPC107476
0.7604	Intermediate Similarity	NPC270013
0.7604	Intermediate Similarity	NPC14961
0.7604	Intermediate Similarity	NPC477922
0.76	Intermediate Similarity	NPC472755
0.759	Intermediate Similarity	NPC4299
0.7586	Intermediate Similarity	NPC11796
0.7586	Intermediate Similarity	NPC218817
0.7582	Intermediate Similarity	NPC474369
0.7582	Intermediate Similarity	NPC99395
0.7582	Intermediate Similarity	NPC21469
0.7582	Intermediate Similarity	NPC475206
0.7582	Intermediate Similarity	NPC261380
0.7582	Intermediate Similarity	NPC197903
0.7579	Intermediate Similarity	NPC109406
0.7579	Intermediate Similarity	NPC159092
0.7576	Intermediate Similarity	NPC472753
0.7573	Intermediate Similarity	NPC313668
0.7573	Intermediate Similarity	NPC315836
0.757	Intermediate Similarity	NPC475642
0.7558	Intermediate Similarity	NPC474447
0.7558	Intermediate Similarity	NPC61863
0.7558	Intermediate Similarity	NPC239127
0.7558	Intermediate Similarity	NPC12740
0.7558	Intermediate Similarity	NPC110461
0.7558	Intermediate Similarity	NPC279537
0.7556	Intermediate Similarity	NPC250315
0.7553	Intermediate Similarity	NPC158388
0.7553	Intermediate Similarity	NPC475855
0.7553	Intermediate Similarity	NPC478003
0.7553	Intermediate Similarity	NPC473448
0.7553	Intermediate Similarity	NPC478004
0.7553	Intermediate Similarity	NPC51004
0.7551	Intermediate Similarity	NPC475653
0.7549	Intermediate Similarity	NPC315531
0.7531	Intermediate Similarity	NPC328653
0.7529	Intermediate Similarity	NPC92558
0.7529	Intermediate Similarity	NPC474551
0.7528	Intermediate Similarity	NPC88735
0.7528	Intermediate Similarity	NPC47031
0.7527	Intermediate Similarity	NPC476805
0.7527	Intermediate Similarity	NPC202672
0.7527	Intermediate Similarity	NPC475819
0.7527	Intermediate Similarity	NPC473715
0.7526	Intermediate Similarity	NPC477921
0.7526	Intermediate Similarity	NPC255410
0.7525	Intermediate Similarity	NPC475676
0.7525	Intermediate Similarity	NPC220964
0.7524	Intermediate Similarity	NPC66108
0.75	Intermediate Similarity	NPC471537
0.75	Intermediate Similarity	NPC475091
0.75	Intermediate Similarity	NPC66110
0.75	Intermediate Similarity	NPC474247
0.75	Intermediate Similarity	NPC477997
0.75	Intermediate Similarity	NPC149371
0.75	Intermediate Similarity	NPC139712
0.75	Intermediate Similarity	NPC81386
0.75	Intermediate Similarity	NPC61527
0.75	Intermediate Similarity	NPC57405
0.75	Intermediate Similarity	NPC474035
0.75	Intermediate Similarity	NPC474709
0.75	Intermediate Similarity	NPC469483
0.75	Intermediate Similarity	NPC476982
0.75	Intermediate Similarity	NPC47220
0.75	Intermediate Similarity	NPC186332
0.75	Intermediate Similarity	NPC303942
0.7474	Intermediate Similarity	NPC471324
0.7474	Intermediate Similarity	NPC261607
0.7474	Intermediate Similarity	NPC473321
0.7474	Intermediate Similarity	NPC476075
0.7474	Intermediate Similarity	NPC111114
0.7474	Intermediate Similarity	NPC300312
0.7474	Intermediate Similarity	NPC476084
0.7474	Intermediate Similarity	NPC206679
0.7474	Intermediate Similarity	NPC114172
0.7473	Intermediate Similarity	NPC3464
0.7473	Intermediate Similarity	NPC475963
0.7473	Intermediate Similarity	NPC70424
0.7473	Intermediate Similarity	NPC243618
0.7473	Intermediate Similarity	NPC158756
0.7473	Intermediate Similarity	NPC151176
0.7471	Intermediate Similarity	NPC107668
0.7471	Intermediate Similarity	NPC477203
0.747	Intermediate Similarity	NPC317583
0.747	Intermediate Similarity	NPC101622

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 NPC477959 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1558
0.2-0.3	3648
0.3-0.4	2314
0.4-0.5	1008
0.5-0.6	355
0.6-0.7	67
0.7-0.8	16
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9529	High Similarity	NPD7983	Approved
0.8889	High Similarity	NPD7839	Suspended
0.8764	High Similarity	NPD5779	Approved
0.8764	High Similarity	NPD5778	Approved
0.8022	Intermediate Similarity	NPD6101	Approved
0.8022	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7154	Phase 3
0.7889	Intermediate Similarity	NPD5786	Approved
0.7849	Intermediate Similarity	NPD6411	Approved
0.7742	Intermediate Similarity	NPD6698	Approved
0.7742	Intermediate Similarity	NPD7838	Discovery
0.7742	Intermediate Similarity	NPD46	Approved
0.766	Intermediate Similarity	NPD7637	Suspended
0.7654	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD4270	Approved
0.764	Intermediate Similarity	NPD4269	Approved
0.7556	Intermediate Similarity	NPD5362	Discontinued
0.7444	Intermediate Similarity	NPD6435	Approved
0.7419	Intermediate Similarity	NPD4250	Approved
0.7419	Intermediate Similarity	NPD4251	Approved
0.7416	Intermediate Similarity	NPD4252	Approved
0.7416	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5363	Approved
0.7374	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5369	Approved
0.7312	Intermediate Similarity	NPD4249	Approved
0.7297	Intermediate Similarity	NPD8513	Phase 3
0.7297	Intermediate Similarity	NPD8516	Approved
0.7297	Intermediate Similarity	NPD8517	Approved
0.7297	Intermediate Similarity	NPD8515	Approved
0.7222	Intermediate Similarity	NPD4819	Approved
0.7222	Intermediate Similarity	NPD4820	Approved
0.7222	Intermediate Similarity	NPD5368	Approved
0.7222	Intermediate Similarity	NPD4821	Approved
0.7222	Intermediate Similarity	NPD4822	Approved
0.7191	Intermediate Similarity	NPD4268	Approved
0.7191	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4271	Approved
0.7188	Intermediate Similarity	NPD5785	Approved
0.7071	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD8039	Approved
0.6991	Remote Similarity	NPD8444	Approved
0.6989	Remote Similarity	NPD5332	Approved
0.6989	Remote Similarity	NPD5331	Approved
0.6983	Remote Similarity	NPD8074	Phase 3
0.6957	Remote Similarity	NPD8299	Approved
0.6957	Remote Similarity	NPD8342	Approved
0.6957	Remote Similarity	NPD4790	Discontinued
0.6957	Remote Similarity	NPD8341	Approved
0.6957	Remote Similarity	NPD8340	Approved
0.6952	Remote Similarity	NPD5048	Discontinued
0.6944	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5370	Suspended
0.687	Remote Similarity	NPD7830	Approved
0.687	Remote Similarity	NPD7829	Approved
0.6852	Remote Similarity	NPD6371	Approved
0.6842	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD8451	Approved
0.6752	Remote Similarity	NPD8273	Phase 1
0.6695	Remote Similarity	NPD8448	Approved
0.6634	Remote Similarity	NPD5282	Discontinued
0.6598	Remote Similarity	NPD6422	Discontinued
0.6579	Remote Similarity	NPD7641	Discontinued
0.6577	Remote Similarity	NPD6053	Discontinued
0.6529	Remote Similarity	NPD8391	Approved
0.6529	Remote Similarity	NPD8390	Approved
0.6529	Remote Similarity	NPD8392	Approved
0.6526	Remote Similarity	NPD5209	Approved
0.6522	Remote Similarity	NPD4756	Discovery
0.6514	Remote Similarity	NPD6686	Approved
0.6495	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6648	Approved
0.6476	Remote Similarity	NPD7639	Approved
0.6476	Remote Similarity	NPD7640	Approved
0.6471	Remote Similarity	NPD3197	Phase 1
0.6458	Remote Similarity	NPD6695	Phase 3
0.6452	Remote Similarity	NPD3732	Approved
0.6415	Remote Similarity	NPD5344	Discontinued
0.6396	Remote Similarity	NPD6421	Discontinued
0.6392	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7638	Approved
0.6381	Remote Similarity	NPD4225	Approved
0.6364	Remote Similarity	NPD7750	Discontinued
0.6348	Remote Similarity	NPD7500	Approved
0.6322	Remote Similarity	NPD7331	Phase 2
0.6316	Remote Similarity	NPD7332	Phase 2
0.6316	Remote Similarity	NPD7514	Phase 3
0.6316	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD8264	Approved
0.6303	Remote Similarity	NPD7642	Approved
0.6289	Remote Similarity	NPD6110	Phase 1
0.6279	Remote Similarity	NPD7909	Approved
0.6277	Remote Similarity	NPD7145	Approved
0.625	Remote Similarity	NPD6902	Approved
0.6238	Remote Similarity	NPD1695	Approved
0.6224	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6399	Phase 3
0.6211	Remote Similarity	NPD6929	Approved
0.6207	Remote Similarity	NPD7115	Discovery
0.6207	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7524	Approved
0.6186	Remote Similarity	NPD6319	Approved
0.6173	Remote Similarity	NPD3195	Phase 2
0.6173	Remote Similarity	NPD3196	Approved
0.6173	Remote Similarity	NPD4266	Approved
0.6173	Remote Similarity	NPD3194	Approved
0.617	Remote Similarity	NPD6925	Approved
0.617	Remote Similarity	NPD5776	Phase 2
0.6167	Remote Similarity	NPD8328	Phase 3
0.6154	Remote Similarity	NPD7748	Approved
0.6147	Remote Similarity	NPD6647	Phase 2
0.6146	Remote Similarity	NPD6930	Phase 2
0.6146	Remote Similarity	NPD6931	Approved
0.614	Remote Similarity	NPD8297	Approved
0.6126	Remote Similarity	NPD6685	Approved
0.6087	Remote Similarity	NPD4732	Discontinued
0.6071	Remote Similarity	NPD6899	Approved
0.6071	Remote Similarity	NPD6881	Approved
0.6053	Remote Similarity	NPD1719	Phase 1
0.6053	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6649	Approved
0.6053	Remote Similarity	NPD6650	Approved
0.6053	Remote Similarity	NPD8130	Phase 1
0.6049	Remote Similarity	NPD3172	Approved
0.6048	Remote Similarity	NPD7319	Approved
0.6036	Remote Similarity	NPD6402	Approved
0.6036	Remote Similarity	NPD7128	Approved
0.6036	Remote Similarity	NPD5739	Approved
0.6036	Remote Similarity	NPD6675	Approved
0.6023	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD7341	Phase 2
0.602	Remote Similarity	NPD7345	Approved
0.602	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6373	Approved
0.6018	Remote Similarity	NPD6372	Approved
0.6016	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD6932	Approved
0.6	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD7492	Approved
0.5982	Remote Similarity	NPD5697	Approved
0.5981	Remote Similarity	NPD7902	Approved
0.5981	Remote Similarity	NPD6083	Phase 2
0.5981	Remote Similarity	NPD6084	Phase 2
0.5968	Remote Similarity	NPD7736	Approved
0.5965	Remote Similarity	NPD7102	Approved
0.5965	Remote Similarity	NPD7290	Approved
0.5965	Remote Similarity	NPD6883	Approved
0.5962	Remote Similarity	NPD7087	Discontinued
0.5962	Remote Similarity	NPD7515	Phase 2
0.5952	Remote Similarity	NPD7260	Phase 2
0.595	Remote Similarity	NPD8080	Discontinued
0.5938	Remote Similarity	NPD8415	Approved
0.5938	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD7507	Approved
0.5935	Remote Similarity	NPD6616	Approved
0.5929	Remote Similarity	NPD7320	Approved
0.5918	Remote Similarity	NPD6898	Phase 1
0.5917	Remote Similarity	NPD6054	Approved
0.5913	Remote Similarity	NPD6869	Approved
0.5913	Remote Similarity	NPD6617	Approved
0.5913	Remote Similarity	NPD6847	Approved
0.5909	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7632	Discontinued
0.59	Remote Similarity	NPD4786	Approved
0.5897	Remote Similarity	NPD6010	Discontinued
0.5887	Remote Similarity	NPD7078	Approved
0.5887	Remote Similarity	NPD8293	Discontinued
0.5877	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6013	Approved
0.5877	Remote Similarity	NPD6012	Approved
0.5877	Remote Similarity	NPD6014	Approved
0.5862	Remote Similarity	NPD6912	Phase 3
0.5859	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD3667	Approved
0.5856	Remote Similarity	NPD5765	Approved
0.5847	Remote Similarity	NPD2629	Approved
0.5842	Remote Similarity	NPD1694	Approved
0.5842	Remote Similarity	NPD6893	Approved
0.5841	Remote Similarity	NPD5701	Approved
0.5841	Remote Similarity	NPD6412	Phase 2
0.5826	Remote Similarity	NPD6420	Discontinued
0.582	Remote Similarity	NPD6370	Approved
0.5812	Remote Similarity	NPD4632	Approved
0.581	Remote Similarity	NPD6079	Approved
0.5802	Remote Similarity	NPD28	Approved
0.5802	Remote Similarity	NPD29	Approved
0.5794	Remote Similarity	NPD5695	Phase 3
0.5789	Remote Similarity	NPD6011	Approved
0.5785	Remote Similarity	NPD6059	Approved
0.5784	Remote Similarity	NPD7146	Approved
0.5784	Remote Similarity	NPD6684	Approved
0.5784	Remote Similarity	NPD5330	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