NPASS Compound

Structure

NPC475711 OpenBabel07101718192D 21 21 0 0 1 0 0 0 0 0999 V2000 0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 9 1 0 0 0 0 4 9 2 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 3 1 6 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 17 1 1 0 0 0 12 6 1 6 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 6 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.14
Volume:	301.635
LogP:	1.243
LogD:	1.422
LogS:	-1.123
# Rotatable Bonds:	7
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.565
Synthetic Accessibility Score:	4.477
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.582
MDCK Permeability:	4.06405160902068e-05
Pgp-inhibitor:	0.715
Pgp-substrate:	0.088
Human Intestinal Absorption (HIA):	0.038
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.466
Plasma Protein Binding (PPB):	30.80119514465332%
Volume Distribution (VD):	0.29
Pgp-substrate:	42.50977325439453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.108
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.558
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.175
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	9.712
Half-life (T1/2):	0.903

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.175
Rat Oral Acute Toxicity:	0.094
Maximum Recommended Daily Dose:	0.911
Skin Sensitization:	0.935
Carcinogencity:	0.857
Eye Corrosion:	0.896
Eye Irritation:	0.569
Respiratory Toxicity:	0.662

Download Data

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

Natural Product: NPC475711

Natural Product ID:	NPC475711
*Common Name:**	6,7-Dihydrophomopsolide B
IUPAC Name:	[(2S,3S)-2-[(3S,4S)-3,4-dihydroxypentyl]-6-oxo-2,3-dihydropyran-3-yl] (E)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	ZFVYHTGRRBKBJE-BUEHMHBYSA-N
Standard InCHI:	InChI=1S/C15H22O6/c1-4-9(2)15(19)21-13-7-8-14(18)20-12(13)6-5-11(17)10(3)16/h4,7-8,10-13,16-17H,5-6H2,1-3H3/b9-4+/t10-,11-,12-,13-/m0/s1
SMILES:	C/C=C(/C(=O)O[C@H]1C=CC(=O)O[C@H]1CC[C@@H]([C@@H](O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512404
PubChem CID:	11460721
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives [CHEMONTID:0001211] Dihydropyranones

*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
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479323]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640527]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	Axinella verrucosa	Mediterranean	n.a.	PMID[14738391]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043411]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Sussex Inlet, New South Wales, Australia	n.a.	PMID[15104517]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332862]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Berkeley Pit lake	n.a.	PMID[17970594]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[19323568]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19326880]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20452770]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	North Sea	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Limonium tubiflorum	n.a.	PMID[21146414]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148349]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22458669]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23360521]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477451]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23603293]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23972215]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24437979]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433188]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392888]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]

☑ 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	60
Others	1

Activity Type	# Activity
Cell Line	59
CELL-LINE	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT399	Cell Line	SF-295	Homo sapiens	IC50	=	17000.0	nM	PMID[477606]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	17000.0	nM	PMID[477606]
NPT398	Cell Line	UACC-62	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT403	Cell Line	UACC-257	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT387	Cell Line	M14	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT375	Cell Line	Malme-3M	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT390	Cell Line	LOX IMVI	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT374	Cell Line	SF-539	Homo sapiens	IC50	=	17000.0	nM	PMID[477606]
NPT383	Cell Line	SNB-19	Homo sapiens	IC50	=	17000.0	nM	PMID[477606]
NPT392	Cell Line	SNB-75	Homo sapiens	IC50	=	17000.0	nM	PMID[477606]
NPT380	Cell Line	U-251	Homo sapiens	IC50	=	17000.0	nM	PMID[477606]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	11000.0	nM	PMID[477606]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	IC50	=	11000.0	nM	PMID[477606]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	11000.0	nM	PMID[477606]
NPT402	Cell Line	Hs-578T	Homo sapiens	IC50	=	11000.0	nM	PMID[477606]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	11000.0	nM	PMID[477606]
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	11000.0	nM	PMID[477606]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	18000.0	nM	PMID[477606]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	18000.0	nM	PMID[477606]
NPT401	Cell Line	786-0	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT376	Cell Line	A498	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT369	Cell Line	ACHN	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT308	Cell Line	CAKI-1	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT406	Cell Line	RXF 393	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT368	Cell Line	SN12C	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT384	Cell Line	TK-10	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT371	Cell Line	UO-31	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT458	Cell Line	IGROV-1	Homo sapiens	IC50	=	18000.0	nM	PMID[477606]
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	=	18000.0	nM	PMID[477606]
NPT456	Cell Line	OVCAR-4	Homo sapiens	IC50	=	18000.0	nM	PMID[477606]
NPT382	Cell Line	OVCAR-5	Homo sapiens	IC50	=	18000.0	nM	PMID[477606]
NPT381	Cell Line	OVCAR-8	Homo sapiens	IC50	=	18000.0	nM	PMID[477606]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	18000.0	nM	PMID[477606]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT389	Cell Line	RPMI-8226	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	18000.0	nM	PMID[477606]
NPT394	Cell Line	EKVX	Homo sapiens	IC50	=	18000.0	nM	PMID[477606]
NPT379	Cell Line	HOP-62	Homo sapiens	IC50	=	18000.0	nM	PMID[477606]
NPT405	Cell Line	NCI-H226	Homo sapiens	IC50	=	18000.0	nM	PMID[477606]
NPT370	Cell Line	NCI-H23	Homo sapiens	IC50	=	18000.0	nM	PMID[477606]
NPT388	Cell Line	NCI-H322M	Homo sapiens	IC50	=	18000.0	nM	PMID[477606]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	18000.0	nM	PMID[477606]
NPT455	Cell Line	NCI-H522	Homo sapiens	IC50	=	18000.0	nM	PMID[477606]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT391	Cell Line	HCC 2998	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT386	Cell Line	KM12	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT323	Cell Line	SW-620	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT372	Cell Line	HOP-92	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT457	Cell Line	BT-549	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT385	Cell Line	SR	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	10.0	mm	PMID[477605]
NPT23303	CELL-LINE	HL-60(TB)	Homo sapiens	IC50	=	2000.0	nM	PMID[477606]

☑ 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 NPC475711 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	173
0.1-0.2	1447
0.2-0.3	5357
0.3-0.4	14019
0.4-0.5	13269
0.5-0.6	5725
0.6-0.7	2141
0.7-0.8	506
0.8-0.85	48
0.85-0.9	6
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9189	High Similarity	NPC474026
0.9067	High Similarity	NPC248775
0.8947	High Similarity	NPC180725
0.8947	High Similarity	NPC470149
0.8947	High Similarity	NPC470148
0.8831	High Similarity	NPC133226
0.8831	High Similarity	NPC470147
0.8649	High Similarity	NPC185186
0.8649	High Similarity	NPC327383
0.8625	High Similarity	NPC474251
0.8514	High Similarity	NPC475762
0.8421	Intermediate Similarity	NPC285840
0.8421	Intermediate Similarity	NPC327041
0.8415	Intermediate Similarity	NPC47937
0.8333	Intermediate Similarity	NPC133450
0.8333	Intermediate Similarity	NPC201356
0.8293	Intermediate Similarity	NPC322529
0.8293	Intermediate Similarity	NPC182383
0.8235	Intermediate Similarity	NPC177668
0.8235	Intermediate Similarity	NPC3952
0.8228	Intermediate Similarity	NPC139712
0.8228	Intermediate Similarity	NPC1180
0.8194	Intermediate Similarity	NPC19769
0.8194	Intermediate Similarity	NPC273600
0.8194	Intermediate Similarity	NPC96414
0.8193	Intermediate Similarity	NPC107717
0.8193	Intermediate Similarity	NPC114694
0.8193	Intermediate Similarity	NPC69082
0.8193	Intermediate Similarity	NPC171174
0.8193	Intermediate Similarity	NPC142117
0.8193	Intermediate Similarity	NPC240695
0.8193	Intermediate Similarity	NPC279267
0.8193	Intermediate Similarity	NPC231096
0.8193	Intermediate Similarity	NPC62118
0.8193	Intermediate Similarity	NPC475581
0.8193	Intermediate Similarity	NPC232555
0.8171	Intermediate Similarity	NPC156804
0.8158	Intermediate Similarity	NPC329914
0.8133	Intermediate Similarity	NPC202011
0.8108	Intermediate Similarity	NPC475760
0.8101	Intermediate Similarity	NPC477314
0.8072	Intermediate Similarity	NPC82795
0.8072	Intermediate Similarity	NPC110710
0.8072	Intermediate Similarity	NPC470124
0.8072	Intermediate Similarity	NPC473651
0.8072	Intermediate Similarity	NPC132496
0.8072	Intermediate Similarity	NPC120398
0.8072	Intermediate Similarity	NPC329838
0.8072	Intermediate Similarity	NPC1083
0.8072	Intermediate Similarity	NPC471494
0.8072	Intermediate Similarity	NPC231009
0.8072	Intermediate Similarity	NPC283085
0.8072	Intermediate Similarity	NPC286338
0.8072	Intermediate Similarity	NPC473478
0.8072	Intermediate Similarity	NPC473669
0.8072	Intermediate Similarity	NPC103284
0.8072	Intermediate Similarity	NPC223871
0.8072	Intermediate Similarity	NPC66346
0.8072	Intermediate Similarity	NPC107986
0.8072	Intermediate Similarity	NPC329615
0.8072	Intermediate Similarity	NPC471567
0.8049	Intermediate Similarity	NPC253801
0.8025	Intermediate Similarity	NPC469469
0.8	Intermediate Similarity	NPC172821
0.8	Intermediate Similarity	NPC40376
0.8	Intermediate Similarity	NPC20339
0.8	Intermediate Similarity	NPC171135
0.8	Intermediate Similarity	NPC234077
0.8	Intermediate Similarity	NPC475004
0.8	Intermediate Similarity	NPC61257
0.8	Intermediate Similarity	NPC169511
0.8	Intermediate Similarity	NPC261952
0.8	Intermediate Similarity	NPC39754
0.8	Intermediate Similarity	NPC81045
0.8	Intermediate Similarity	NPC133730
0.8	Intermediate Similarity	NPC274446
0.8	Intermediate Similarity	NPC280621
0.8	Intermediate Similarity	NPC191929
0.8	Intermediate Similarity	NPC21208
0.8	Intermediate Similarity	NPC242364
0.8	Intermediate Similarity	NPC320569
0.8	Intermediate Similarity	NPC151403
0.8	Intermediate Similarity	NPC48338
0.8	Intermediate Similarity	NPC100454
0.8	Intermediate Similarity	NPC233551
0.8	Intermediate Similarity	NPC287164
0.7976	Intermediate Similarity	NPC134885
0.7976	Intermediate Similarity	NPC293136
0.7976	Intermediate Similarity	NPC134865
0.7976	Intermediate Similarity	NPC103523
0.7976	Intermediate Similarity	NPC134807
0.7976	Intermediate Similarity	NPC208473
0.7976	Intermediate Similarity	NPC309211
0.7976	Intermediate Similarity	NPC112685
0.7976	Intermediate Similarity	NPC219498
0.7976	Intermediate Similarity	NPC241360
0.7976	Intermediate Similarity	NPC132940
0.7976	Intermediate Similarity	NPC308412
0.7976	Intermediate Similarity	NPC311163
0.7976	Intermediate Similarity	NPC473687
0.7976	Intermediate Similarity	NPC204686
0.7976	Intermediate Similarity	NPC210218
0.7975	Intermediate Similarity	NPC233071
0.7955	Intermediate Similarity	NPC256368
0.7952	Intermediate Similarity	NPC475035
0.7952	Intermediate Similarity	NPC163093
0.7927	Intermediate Similarity	NPC329829
0.7927	Intermediate Similarity	NPC65930
0.7927	Intermediate Similarity	NPC475159
0.7927	Intermediate Similarity	NPC11332
0.7927	Intermediate Similarity	NPC145914
0.7927	Intermediate Similarity	NPC73310
0.7927	Intermediate Similarity	NPC473529
0.7927	Intermediate Similarity	NPC473780
0.7927	Intermediate Similarity	NPC94875
0.7927	Intermediate Similarity	NPC131002
0.7927	Intermediate Similarity	NPC473712
0.7927	Intermediate Similarity	NPC180363
0.7922	Intermediate Similarity	NPC329890
0.7907	Intermediate Similarity	NPC20621
0.7907	Intermediate Similarity	NPC81778
0.7907	Intermediate Similarity	NPC40066
0.7907	Intermediate Similarity	NPC473504
0.7907	Intermediate Similarity	NPC42598
0.7907	Intermediate Similarity	NPC477011
0.7907	Intermediate Similarity	NPC318963
0.7907	Intermediate Similarity	NPC93794
0.7907	Intermediate Similarity	NPC91067
0.7895	Intermediate Similarity	NPC476012
0.7882	Intermediate Similarity	NPC473995
0.7882	Intermediate Similarity	NPC178215
0.7882	Intermediate Similarity	NPC476583
0.7882	Intermediate Similarity	NPC20533
0.7882	Intermediate Similarity	NPC258068
0.7867	Intermediate Similarity	NPC474823
0.7857	Intermediate Similarity	NPC77871
0.7857	Intermediate Similarity	NPC9678
0.7857	Intermediate Similarity	NPC473671
0.7857	Intermediate Similarity	NPC100921
0.7857	Intermediate Similarity	NPC292809
0.7857	Intermediate Similarity	NPC475268
0.7857	Intermediate Similarity	NPC470400
0.7857	Intermediate Similarity	NPC39279
0.7857	Intermediate Similarity	NPC235809
0.7857	Intermediate Similarity	NPC477018
0.7857	Intermediate Similarity	NPC477014
0.7857	Intermediate Similarity	NPC319036
0.7857	Intermediate Similarity	NPC477013
0.7857	Intermediate Similarity	NPC39167
0.7857	Intermediate Similarity	NPC25764
0.7857	Intermediate Similarity	NPC202055
0.7857	Intermediate Similarity	NPC473156
0.7848	Intermediate Similarity	NPC188860
0.7848	Intermediate Similarity	NPC326661
0.7841	Intermediate Similarity	NPC472196
0.7841	Intermediate Similarity	NPC472195
0.7841	Intermediate Similarity	NPC238090
0.7838	Intermediate Similarity	NPC475555
0.7838	Intermediate Similarity	NPC276299
0.7838	Intermediate Similarity	NPC475675
0.7831	Intermediate Similarity	NPC44261
0.7831	Intermediate Similarity	NPC144415
0.7816	Intermediate Similarity	NPC239517
0.7816	Intermediate Similarity	NPC473904
0.7805	Intermediate Similarity	NPC297440
0.7791	Intermediate Similarity	NPC89001
0.7791	Intermediate Similarity	NPC473905
0.7791	Intermediate Similarity	NPC320458
0.7778	Intermediate Similarity	NPC86971
0.7778	Intermediate Similarity	NPC473947
0.7765	Intermediate Similarity	NPC473840
0.7765	Intermediate Similarity	NPC477010
0.7765	Intermediate Similarity	NPC219652
0.7765	Intermediate Similarity	NPC282815
0.7765	Intermediate Similarity	NPC25703
0.7765	Intermediate Similarity	NPC477015
0.7763	Intermediate Similarity	NPC475982
0.7753	Intermediate Similarity	NPC159698
0.7746	Intermediate Similarity	NPC159650
0.7746	Intermediate Similarity	NPC22897
0.7738	Intermediate Similarity	NPC186155
0.7738	Intermediate Similarity	NPC160517
0.7738	Intermediate Similarity	NPC266718
0.7738	Intermediate Similarity	NPC78673
0.7738	Intermediate Similarity	NPC473308
0.7711	Intermediate Similarity	NPC251026
0.7701	Intermediate Similarity	NPC477017
0.7701	Intermediate Similarity	NPC14901
0.7701	Intermediate Similarity	NPC130359
0.7701	Intermediate Similarity	NPC477016
0.7701	Intermediate Similarity	NPC139418
0.7692	Intermediate Similarity	NPC475332
0.7692	Intermediate Similarity	NPC477085
0.7692	Intermediate Similarity	NPC477311
0.7692	Intermediate Similarity	NPC477303
0.7674	Intermediate Similarity	NPC159750
0.7674	Intermediate Similarity	NPC473649
0.7674	Intermediate Similarity	NPC470401
0.7674	Intermediate Similarity	NPC154097
0.7674	Intermediate Similarity	NPC475037

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 NPC475711 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	1985
0.2-0.3	3833
0.3-0.4	2280
0.4-0.5	719
0.5-0.6	157
0.6-0.7	30
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8023	Intermediate Similarity	NPD7838	Discovery
0.7816	Intermediate Similarity	NPD46	Approved
0.7816	Intermediate Similarity	NPD6698	Approved
0.7419	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5344	Discontinued
0.6957	Remote Similarity	NPD7983	Approved
0.6804	Remote Similarity	NPD6648	Approved
0.6701	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6593	Remote Similarity	NPD4249	Approved
0.6582	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6371	Approved
0.6522	Remote Similarity	NPD4251	Approved
0.6522	Remote Similarity	NPD4250	Approved
0.6512	Remote Similarity	NPD4756	Discovery
0.6484	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD3197	Phase 1
0.642	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7638	Approved
0.6316	Remote Similarity	NPD5785	Approved
0.6304	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7639	Approved
0.63	Remote Similarity	NPD7640	Approved
0.6282	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD7154	Phase 3
0.6264	Remote Similarity	NPD6110	Phase 1
0.625	Remote Similarity	NPD4271	Approved
0.625	Remote Similarity	NPD4268	Approved
0.6234	Remote Similarity	NPD69	Approved
0.6234	Remote Similarity	NPD6109	Phase 1
0.6234	Remote Similarity	NPD9119	Approved
0.6234	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5779	Approved
0.6186	Remote Similarity	NPD5778	Approved
0.6162	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5209	Approved
0.6129	Remote Similarity	NPD5363	Approved
0.6111	Remote Similarity	NPD4820	Approved
0.6111	Remote Similarity	NPD4819	Approved
0.6111	Remote Similarity	NPD4822	Approved
0.6111	Remote Similarity	NPD4821	Approved
0.6111	Remote Similarity	NPD6053	Discontinued
0.6106	Remote Similarity	NPD7503	Approved
0.6104	Remote Similarity	NPD9118	Approved
0.6087	Remote Similarity	NPD5362	Discontinued
0.6082	Remote Similarity	NPD7637	Suspended
0.6042	Remote Similarity	NPD1695	Approved
0.6036	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD7829	Approved
0.6	Remote Similarity	NPD7839	Suspended
0.6	Remote Similarity	NPD7830	Approved
0.5981	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD8513	Phase 3
0.5957	Remote Similarity	NPD1694	Approved
0.5946	Remote Similarity	NPD6927	Phase 3
0.5926	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD5331	Approved
0.5914	Remote Similarity	NPD5332	Approved
0.5909	Remote Similarity	NPD8039	Approved
0.5904	Remote Similarity	NPD3704	Approved
0.587	Remote Similarity	NPD4790	Discontinued
0.5862	Remote Similarity	NPD7642	Approved
0.5841	Remote Similarity	NPD7328	Approved
0.5841	Remote Similarity	NPD7641	Discontinued
0.5841	Remote Similarity	NPD7327	Approved
0.5826	Remote Similarity	NPD8516	Approved
0.5826	Remote Similarity	NPD8033	Approved
0.5826	Remote Similarity	NPD8515	Approved
0.5826	Remote Similarity	NPD8517	Approved
0.5816	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD4269	Approved
0.5806	Remote Similarity	NPD4270	Approved
0.5806	Remote Similarity	NPD6435	Approved
0.58	Remote Similarity	NPD5282	Discontinued
0.5789	Remote Similarity	NPD7516	Approved
0.5789	Remote Similarity	NPD3172	Approved
0.578	Remote Similarity	NPD6421	Discontinued
0.5766	Remote Similarity	NPD4632	Approved
0.5761	Remote Similarity	NPD4252	Approved
0.5752	Remote Similarity	NPD7500	Approved
0.5752	Remote Similarity	NPD7505	Discontinued
0.5739	Remote Similarity	NPD8294	Approved
0.5739	Remote Similarity	NPD8377	Approved
0.5729	Remote Similarity	NPD5786	Approved
0.5727	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3196	Approved
0.5714	Remote Similarity	NPD4266	Approved
0.5714	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3195	Phase 2
0.5714	Remote Similarity	NPD6101	Approved
0.5714	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7632	Discontinued
0.5714	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3194	Approved
0.5701	Remote Similarity	NPD4211	Phase 1
0.5699	Remote Similarity	NPD5369	Approved
0.569	Remote Similarity	NPD8296	Approved
0.569	Remote Similarity	NPD8380	Approved
0.569	Remote Similarity	NPD8335	Approved
0.569	Remote Similarity	NPD8444	Approved
0.569	Remote Similarity	NPD8379	Approved
0.569	Remote Similarity	NPD8378	Approved
0.567	Remote Similarity	NPD7524	Approved
0.5663	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.566	Remote Similarity	NPD1407	Approved
0.566	Remote Similarity	NPD6647	Phase 2
0.5648	Remote Similarity	NPD6412	Phase 2
0.5636	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.563	Remote Similarity	NPD7507	Approved
0.563	Remote Similarity	NPD8273	Phase 1
0.561	Remote Similarity	NPD368	Approved
0.5603	Remote Similarity	NPD6319	Approved
0.56	Remote Similarity	NPD6411	Approved
0.56	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