NPASS Compound

Structure

CID329490 OpenBabel06191716212D 21 23 0 0 1 0 0 0 0 0999 V2000 3.1541 -2.7302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0315 -2.6094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1211 -2.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7887 0.4548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 -2.7313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3649 -0.4558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3647 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7881 -2.2761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 -0.9104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3656 -2.2753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7888 -2.2758 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7886 -1.3653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5768 -0.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5764 -1.8209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7885 -0.4555 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7883 -1.3656 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3653 -1.3649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5770 0.9098 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5773 -2.7307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7884 -0.4552 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 10 1 0 0 0 0 2 14 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 8 1 0 0 0 0 5 11 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 19 1 1 0 0 0 12 9 1 6 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 18 2 0 0 0 0 14 16 1 0 0 0 0 15 16 1 1 0 0 0 15 21 1 0 0 0 0 16 8 1 1 0 0 0 20 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.16
Volume:	298.301
LogP:	2.345
LogD:	2.643
LogS:	-3.939
# Rotatable Bonds:	2
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.55
Synthetic Accessibility Score:	5.693
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.734
MDCK Permeability:	2.669434434210416e-05
Pgp-inhibitor:	0.519
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.342

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.491
Plasma Protein Binding (PPB):	61.99633026123047%
Volume Distribution (VD):	1.157
Pgp-substrate:	52.21094512939453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.481
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.068
CYP2C9-substrate:	0.201
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.69
CYP3A4-inhibitor:	0.208
CYP3A4-substrate:	0.785

ADMET: Excretion

Clearance (CL):	6.076
Half-life (T1/2):	0.814

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.443
Drug-inuced Liver Injury (DILI):	0.657
AMES Toxicity:	0.898
Rat Oral Acute Toxicity:	0.382
Maximum Recommended Daily Dose:	0.268
Skin Sensitization:	0.346
Carcinogencity:	0.893
Eye Corrosion:	0.906
Eye Irritation:	0.944
Respiratory Toxicity:	0.723

Download Data

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

Natural Product: NPC329490

Natural Product ID:	NPC329490
*Common Name:**	Talaperoxide B
IUPAC Name:	n.a.
Synonyms:	talaperoxide B
Standard InCHIKey:	KLVLZPYIONMIPB-GVAFMPQTSA-N
Standard InCHI:	InChI=1S/C16H24O5/c1-10(17)19-11-5-8-16-9-12(11)20-21-15(16,4)13(18)6-7-14(16,2)3/h11-12H,5-9H2,1-4H3/t11-,12-,15-,16+/m0/s1
SMILES:	CC(=O)OC1CCC23CC1OOC2(C(=O)CCC3(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1784534
PubChem CID:	54583336
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000368] Dioxanes [CHEMONTID:0001312] 1,2-dioxanes

*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
NPO25220	Talaromyces flavus	Species	Trichocomaceae	Eukaryota	Isolated from fresh, healthy leaves of Sonneratia apetala	Dongzhaigang Mangrove National Nature Reserve in Hainan Island, China	2009-APR	PMID[21545109]
NPO25220	Talaromyces flavus	Species	Trichocomaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21545109]
NPO25220	Talaromyces flavus	Species	Trichocomaceae	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
IC50	5
LD50	1

Activity Type	# Activity
Cell Line	5
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1.33	ug.mL-1	PMID[535643]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	2.78	ug.mL-1	PMID[535643]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	1.29	ug.mL-1	PMID[535643]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	1.73	ug.mL-1	PMID[535643]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	0.89	ug.mL-1	PMID[535643]
NPT176	Organism	Artemia salina	Artemia salina	LD50	<	10.0	ppm	PMID[535643]

☑ 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 NPC329490 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	522
0.1-0.2	3853
0.2-0.3	8509
0.3-0.4	14786
0.4-0.5	6710
0.5-0.6	5631
0.6-0.7	2466
0.7-0.8	210
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC328639
0.8395	Intermediate Similarity	NPC125366
0.8375	Intermediate Similarity	NPC478084
0.8353	Intermediate Similarity	NPC470920
0.8295	Intermediate Similarity	NPC474379
0.8267	Intermediate Similarity	NPC329466
0.8267	Intermediate Similarity	NPC328304
0.8182	Intermediate Similarity	NPC216137
0.8046	Intermediate Similarity	NPC236459
0.8023	Intermediate Similarity	NPC248216
0.8023	Intermediate Similarity	NPC477441
0.7952	Intermediate Similarity	NPC134227
0.7875	Intermediate Similarity	NPC55508
0.7802	Intermediate Similarity	NPC477495
0.7753	Intermediate Similarity	NPC477443
0.7753	Intermediate Similarity	NPC477440
0.7701	Intermediate Similarity	NPC477205
0.7674	Intermediate Similarity	NPC269684
0.7667	Intermediate Similarity	NPC477444
0.7667	Intermediate Similarity	NPC477442
0.7667	Intermediate Similarity	NPC477433
0.764	Intermediate Similarity	NPC476435
0.764	Intermediate Similarity	NPC476379
0.7614	Intermediate Similarity	NPC120395
0.7609	Intermediate Similarity	NPC309127
0.7609	Intermediate Similarity	NPC247877
0.759	Intermediate Similarity	NPC143250
0.7586	Intermediate Similarity	NPC9060
0.7586	Intermediate Similarity	NPC477434
0.7586	Intermediate Similarity	NPC181871
0.7586	Intermediate Similarity	NPC237938
0.7586	Intermediate Similarity	NPC219535
0.7586	Intermediate Similarity	NPC65133
0.7553	Intermediate Similarity	NPC266417
0.7531	Intermediate Similarity	NPC109510
0.75	Intermediate Similarity	NPC477445
0.75	Intermediate Similarity	NPC474572
0.7473	Intermediate Similarity	NPC185529
0.7473	Intermediate Similarity	NPC472146
0.7471	Intermediate Similarity	NPC227170
0.7471	Intermediate Similarity	NPC476721
0.747	Intermediate Similarity	NPC471046
0.7447	Intermediate Similarity	NPC476728
0.7447	Intermediate Similarity	NPC163685
0.7447	Intermediate Similarity	NPC235109
0.7442	Intermediate Similarity	NPC45256
0.7442	Intermediate Similarity	NPC285480
0.7442	Intermediate Similarity	NPC30443
0.7442	Intermediate Similarity	NPC260977
0.7423	Intermediate Similarity	NPC471254
0.7416	Intermediate Similarity	NPC475729
0.7416	Intermediate Similarity	NPC474215
0.7416	Intermediate Similarity	NPC83242
0.74	Intermediate Similarity	NPC289702
0.74	Intermediate Similarity	NPC208461
0.7386	Intermediate Similarity	NPC475689
0.7368	Intermediate Similarity	NPC471241
0.7363	Intermediate Similarity	NPC67653
0.7363	Intermediate Similarity	NPC471459
0.7363	Intermediate Similarity	NPC200580
0.7347	Intermediate Similarity	NPC471253
0.734	Intermediate Similarity	NPC82633
0.734	Intermediate Similarity	NPC287354
0.734	Intermediate Similarity	NPC62407
0.734	Intermediate Similarity	NPC217329
0.7333	Intermediate Similarity	NPC239938
0.7326	Intermediate Similarity	NPC60568
0.7303	Intermediate Similarity	NPC473350
0.7292	Intermediate Similarity	NPC17183
0.7292	Intermediate Similarity	NPC253995
0.7283	Intermediate Similarity	NPC77756
0.7283	Intermediate Similarity	NPC470114
0.7283	Intermediate Similarity	NPC18536
0.7283	Intermediate Similarity	NPC50443
0.7273	Intermediate Similarity	NPC15091
0.7263	Intermediate Similarity	NPC256227
0.7263	Intermediate Similarity	NPC475765
0.7263	Intermediate Similarity	NPC475785
0.7263	Intermediate Similarity	NPC219353
0.7263	Intermediate Similarity	NPC477264
0.7253	Intermediate Similarity	NPC471221
0.7253	Intermediate Similarity	NPC473319
0.7253	Intermediate Similarity	NPC131104
0.7253	Intermediate Similarity	NPC3032
0.7253	Intermediate Similarity	NPC221993
0.7245	Intermediate Similarity	NPC470172
0.7241	Intermediate Similarity	NPC476071
0.7234	Intermediate Similarity	NPC470424
0.7229	Intermediate Similarity	NPC96759
0.7228	Intermediate Similarity	NPC293850
0.7222	Intermediate Similarity	NPC476717
0.7222	Intermediate Similarity	NPC476726
0.7222	Intermediate Similarity	NPC80700
0.7222	Intermediate Similarity	NPC472272
0.7222	Intermediate Similarity	NPC476727
0.7209	Intermediate Similarity	NPC477287
0.7204	Intermediate Similarity	NPC52756
0.7204	Intermediate Similarity	NPC476934
0.72	Intermediate Similarity	NPC181357
0.7195	Intermediate Similarity	NPC96322
0.7191	Intermediate Similarity	NPC473299
0.7191	Intermediate Similarity	NPC471044
0.7191	Intermediate Similarity	NPC473336
0.7188	Intermediate Similarity	NPC472273
0.7188	Intermediate Similarity	NPC74466
0.7172	Intermediate Similarity	NPC473406
0.7159	Intermediate Similarity	NPC121121
0.7158	Intermediate Similarity	NPC305808
0.7158	Intermediate Similarity	NPC470031
0.7157	Intermediate Similarity	NPC27814
0.7157	Intermediate Similarity	NPC474242
0.7143	Intermediate Similarity	NPC252614
0.7143	Intermediate Similarity	NPC298266
0.7143	Intermediate Similarity	NPC259654
0.7129	Intermediate Similarity	NPC3316
0.7129	Intermediate Similarity	NPC203974
0.7129	Intermediate Similarity	NPC144854
0.7128	Intermediate Similarity	NPC472148
0.7128	Intermediate Similarity	NPC472147
0.7128	Intermediate Similarity	NPC476189
0.7126	Intermediate Similarity	NPC1882
0.7113	Intermediate Similarity	NPC472144
0.7113	Intermediate Similarity	NPC474724
0.7111	Intermediate Similarity	NPC476715
0.7108	Intermediate Similarity	NPC474755
0.7108	Intermediate Similarity	NPC123122
0.71	Intermediate Similarity	NPC88469
0.71	Intermediate Similarity	NPC65523
0.7097	Intermediate Similarity	NPC88337
0.7097	Intermediate Similarity	NPC475211
0.7093	Intermediate Similarity	NPC475725
0.7087	Intermediate Similarity	NPC100908
0.7083	Intermediate Similarity	NPC193785
0.7059	Intermediate Similarity	NPC277017
0.7059	Intermediate Similarity	NPC474020
0.7059	Intermediate Similarity	NPC154608
0.7059	Intermediate Similarity	NPC192813
0.7053	Intermediate Similarity	NPC470423
0.7048	Intermediate Similarity	NPC49451
0.7048	Intermediate Similarity	NPC7921
0.7048	Intermediate Similarity	NPC208998
0.7045	Intermediate Similarity	NPC470154
0.7045	Intermediate Similarity	NPC470156
0.7045	Intermediate Similarity	NPC475743
0.7041	Intermediate Similarity	NPC293890
0.7041	Intermediate Similarity	NPC472972
0.7033	Intermediate Similarity	NPC243746
0.7033	Intermediate Similarity	NPC474008
0.7021	Intermediate Similarity	NPC475878
0.7021	Intermediate Similarity	NPC470230
0.7021	Intermediate Similarity	NPC198054
0.7019	Intermediate Similarity	NPC171888
0.7019	Intermediate Similarity	NPC201992
0.7019	Intermediate Similarity	NPC146945
0.7013	Intermediate Similarity	NPC204173
0.7011	Intermediate Similarity	NPC201276
0.7011	Intermediate Similarity	NPC73013
0.7011	Intermediate Similarity	NPC320144
0.7011	Intermediate Similarity	NPC80891
0.7011	Intermediate Similarity	NPC275243
0.701	Intermediate Similarity	NPC470632
0.701	Intermediate Similarity	NPC472145
0.7	Intermediate Similarity	NPC277074
0.7	Intermediate Similarity	NPC291310
0.7	Intermediate Similarity	NPC79308
0.7	Intermediate Similarity	NPC209298
0.7	Intermediate Similarity	NPC84562
0.7	Intermediate Similarity	NPC122811
0.699	Remote Similarity	NPC208333
0.699	Remote Similarity	NPC236753
0.699	Remote Similarity	NPC228190
0.699	Remote Similarity	NPC227879
0.699	Remote Similarity	NPC141350
0.6988	Remote Similarity	NPC478227
0.6981	Remote Similarity	NPC45218
0.6981	Remote Similarity	NPC268238
0.6981	Remote Similarity	NPC473798
0.6981	Remote Similarity	NPC143268
0.6981	Remote Similarity	NPC299849
0.6981	Remote Similarity	NPC323821
0.6979	Remote Similarity	NPC17336
0.6977	Remote Similarity	NPC112463
0.6977	Remote Similarity	NPC307865
0.6977	Remote Similarity	NPC471151
0.6966	Remote Similarity	NPC477284
0.6966	Remote Similarity	NPC477446
0.6966	Remote Similarity	NPC470155
0.6966	Remote Similarity	NPC289486
0.6966	Remote Similarity	NPC477447
0.6966	Remote Similarity	NPC61107
0.6961	Remote Similarity	NPC202524
0.6961	Remote Similarity	NPC186054
0.6961	Remote Similarity	NPC471474
0.6957	Remote Similarity	NPC263802
0.6952	Remote Similarity	NPC11252
0.6952	Remote Similarity	NPC474516
0.6952	Remote Similarity	NPC289312
0.6947	Remote Similarity	NPC469315
0.6941	Remote Similarity	NPC159789
0.6939	Remote Similarity	NPC474793

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 NPC329490 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	575
0.1-0.2	3849
0.2-0.3	3048
0.3-0.4	1089
0.4-0.5	303
0.5-0.6	211
0.6-0.7	65
0.7-0.8	10
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
0.7442	Intermediate Similarity	NPD1780	Approved
0.7442	Intermediate Similarity	NPD1779	Approved
0.74	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3703	Phase 2
0.6897	Remote Similarity	NPD6697	Approved
0.6897	Remote Similarity	NPD6118	Approved
0.6897	Remote Similarity	NPD6115	Approved
0.6897	Remote Similarity	NPD6114	Approved
0.68	Remote Similarity	NPD1700	Approved
0.6786	Remote Similarity	NPD5777	Approved
0.6782	Remote Similarity	NPD6116	Phase 1
0.6744	Remote Similarity	NPD3702	Approved
0.6703	Remote Similarity	NPD3669	Approved
0.6703	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6117	Approved
0.6607	Remote Similarity	NPD6921	Approved
0.6574	Remote Similarity	NPD4632	Approved
0.6538	Remote Similarity	NPD6008	Approved
0.6509	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2687	Approved
0.6471	Remote Similarity	NPD2254	Approved
0.6471	Remote Similarity	NPD2686	Approved
0.6442	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD3573	Approved
0.6396	Remote Similarity	NPD6009	Approved
0.6396	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6402	Approved
0.6381	Remote Similarity	NPD5739	Approved
0.6381	Remote Similarity	NPD6675	Approved
0.6381	Remote Similarity	NPD7128	Approved
0.6372	Remote Similarity	NPD6319	Approved
0.6355	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.633	Remote Similarity	NPD8297	Approved
0.6321	Remote Similarity	NPD5701	Approved
0.6321	Remote Similarity	NPD5697	Approved
0.6316	Remote Similarity	NPD5983	Phase 2
0.6296	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6881	Approved
0.6262	Remote Similarity	NPD7320	Approved
0.6262	Remote Similarity	NPD6899	Approved
0.6262	Remote Similarity	NPD6011	Approved
0.6207	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7604	Phase 2
0.6207	Remote Similarity	NPD8328	Phase 3
0.6204	Remote Similarity	NPD6014	Approved
0.6204	Remote Similarity	NPD6013	Approved
0.6204	Remote Similarity	NPD6372	Approved
0.6204	Remote Similarity	NPD6373	Approved
0.6204	Remote Similarity	NPD6012	Approved
0.62	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7900	Approved
0.619	Remote Similarity	NPD4224	Phase 2
0.6162	Remote Similarity	NPD8035	Phase 2
0.6162	Remote Similarity	NPD8034	Phase 2
0.6154	Remote Similarity	NPD7492	Approved
0.6147	Remote Similarity	NPD6883	Approved
0.6147	Remote Similarity	NPD7102	Approved
0.6147	Remote Similarity	NPD7290	Approved
0.6102	Remote Similarity	NPD6336	Discontinued
0.6102	Remote Similarity	NPD6616	Approved
0.6092	Remote Similarity	NPD4789	Approved
0.6091	Remote Similarity	NPD6650	Approved
0.6091	Remote Similarity	NPD6617	Approved
0.6091	Remote Similarity	NPD8130	Phase 1
0.6091	Remote Similarity	NPD6649	Approved
0.6091	Remote Similarity	NPD6847	Approved
0.6091	Remote Similarity	NPD6869	Approved
0.6091	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6059	Approved
0.6087	Remote Similarity	NPD6054	Approved
0.6067	Remote Similarity	NPD1810	Approved
0.6067	Remote Similarity	NPD1811	Approved
0.605	Remote Similarity	NPD7078	Approved
0.605	Remote Similarity	NPD8293	Discontinued
0.6047	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD229	Approved
0.6047	Remote Similarity	NPD5360	Phase 3
0.604	Remote Similarity	NPD7748	Approved
0.6036	Remote Similarity	NPD6882	Approved
0.6034	Remote Similarity	NPD6016	Approved
0.6034	Remote Similarity	NPD6015	Approved
0.6023	Remote Similarity	NPD6081	Approved
0.602	Remote Similarity	NPD6672	Approved
0.602	Remote Similarity	NPD5737	Approved
0.6019	Remote Similarity	NPD4755	Approved
0.6019	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD7736	Approved
0.5983	Remote Similarity	NPD5988	Approved
0.5983	Remote Similarity	NPD6370	Approved
0.5982	Remote Similarity	NPD8133	Approved
0.5977	Remote Similarity	NPD3698	Phase 2
0.5952	Remote Similarity	NPD371	Approved
0.5941	Remote Similarity	NPD6399	Phase 3
0.5909	Remote Similarity	NPD4245	Approved
0.5909	Remote Similarity	NPD4244	Approved
0.5905	Remote Similarity	NPD5285	Approved
0.5905	Remote Similarity	NPD4696	Approved
0.5905	Remote Similarity	NPD5286	Approved
0.5905	Remote Similarity	NPD4700	Approved
0.5882	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6274	Approved
0.5876	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD4634	Approved
0.5849	Remote Similarity	NPD5223	Approved
0.5843	Remote Similarity	NPD4758	Discontinued
0.5842	Remote Similarity	NPD7515	Phase 2
0.5833	Remote Similarity	NPD7507	Approved
0.5826	Remote Similarity	NPD6317	Approved
0.5818	Remote Similarity	NPD6686	Approved
0.5816	Remote Similarity	NPD6684	Approved
0.5816	Remote Similarity	NPD7334	Approved
0.5816	Remote Similarity	NPD7146	Approved
0.5816	Remote Similarity	NPD5330	Approved
0.5816	Remote Similarity	NPD7521	Approved
0.5816	Remote Similarity	NPD6098	Approved
0.5816	Remote Similarity	NPD6409	Approved
0.581	Remote Similarity	NPD7638	Approved
0.5806	Remote Similarity	NPD3671	Phase 1
0.58	Remote Similarity	NPD6080	Approved
0.58	Remote Similarity	NPD6673	Approved
0.58	Remote Similarity	NPD6904	Approved
0.5794	Remote Similarity	NPD5224	Approved
0.5794	Remote Similarity	NPD8301	Approved
0.5794	Remote Similarity	NPD5225	Approved
0.5794	Remote Similarity	NPD8300	Approved
0.5794	Remote Similarity	NPD5226	Approved
0.5794	Remote Similarity	NPD5211	Phase 2
0.5794	Remote Similarity	NPD4633	Approved
0.5776	Remote Similarity	NPD6313	Approved
0.5776	Remote Similarity	NPD6335	Approved
0.5776	Remote Similarity	NPD6314	Approved
0.5769	Remote Similarity	NPD4697	Phase 3
0.5769	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5221	Approved
0.5769	Remote Similarity	NPD5222	Approved
0.5755	Remote Similarity	NPD7640	Approved
0.5755	Remote Similarity	NPD7639	Approved
0.5741	Remote Similarity	NPD5175	Approved
0.5741	Remote Similarity	NPD5174	Approved
0.5741	Remote Similarity	NPD4754	Approved
0.5739	Remote Similarity	NPD6940	Discontinued
0.5738	Remote Similarity	NPD6033	Approved
0.573	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6412	Phase 2
0.5726	Remote Similarity	NPD7101	Approved
0.5726	Remote Similarity	NPD7100	Approved
0.5714	Remote Similarity	NPD6083	Phase 2
0.5714	Remote Similarity	NPD6084	Phase 2
0.5714	Remote Similarity	NPD5173	Approved
0.57	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.57	Remote Similarity	NPD6903	Approved
0.5691	Remote Similarity	NPD7319	Approved
0.5688	Remote Similarity	NPD5141	Approved
0.5686	Remote Similarity	NPD5693	Phase 1
0.5686	Remote Similarity	NPD6411	Approved
0.5684	Remote Similarity	NPD6928	Phase 2
0.5673	Remote Similarity	NPD5695	Phase 3
0.5673	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.566	Remote Similarity	NPD5696	Approved
0.5648	Remote Similarity	NPD7632	Discontinued
0.5644	Remote Similarity	NPD5328	Approved
0.5638	Remote Similarity	NPD5364	Discontinued
0.5638	Remote Similarity	NPD4802	Phase 2
0.5638	Remote Similarity	NPD4238	Approved
0.5636	Remote Similarity	NPD4768	Approved
0.5636	Remote Similarity	NPD4767	Approved
0.563	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.563	Remote Similarity	NPD6908	Approved
0.563	Remote Similarity	NPD6909	Approved
0.5625	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD3726	Approved
0.5618	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD3725	Approved
0.5607	Remote Similarity	NPD8418	Phase 2
0.5603	Remote Similarity	NPD6868	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