NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.15
Volume:	257.555
LogP:	2.13
LogD:	1.673
LogS:	-3.68
# Rotatable Bonds:	0
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.672
Synthetic Accessibility Score:	5.815
Fsp3:	0.929
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:	-4.78
MDCK Permeability:	1.6274041627184488e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.138
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.239

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.393
Plasma Protein Binding (PPB):	73.00586700439453%
Volume Distribution (VD):	1.66
Pgp-substrate:	38.93161392211914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.904
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.894
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.24
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.391
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.749

ADMET: Excretion

Clearance (CL):	8.155
Half-life (T1/2):	0.705

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.597
Drug-inuced Liver Injury (DILI):	0.253
AMES Toxicity:	0.911
Rat Oral Acute Toxicity:	0.831
Maximum Recommended Daily Dose:	0.633
Skin Sensitization:	0.357
Carcinogencity:	0.969
Eye Corrosion:	0.532
Eye Irritation:	0.931
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC478084

Natural Product ID:	NPC478084
*Common Name:**	Merulin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QYJVCFQEMCWLHS-MHWZDGSBSA-N
Standard InCHI:	InChI=1S/C14H22O4/c1-12(2)6-5-11(16)13(3)14(12)7-4-9(15)10(8-14)17-18-13/h9-10,15H,4-8H2,1-3H3/t9-,10-,13-,14+/m1/s1
SMILES:	O[C@@H]1CC[C@]23C[C@H]1OO[C@]3(C)C(=O)CCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1784537
PubChem CID:	46831716
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
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	rind	n.a.	DOI[10.1002/hlca.200800177]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17323995]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[17450509]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	seed kernels	n.a.	n.a.	PMID[19908853]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20411928]
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]
NPO33551	Thai mangrove-derived fungus	Species	n.a.	n.a.	isolated from the leaves of Xylocarpus granatum	Samutsakorn Province, Thailand	2008-JUL	PMID[21954864]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31895570]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	7
LD50	1

Activity Type	# Activity
Cell Line	7
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT845	Cell Line	BT-474	Homo sapiens	IC50	=	4.98	ug.mL-1	PMID[482439]
NPT323	Cell Line	SW-620	Homo sapiens	IC50	=	4.84	ug.mL-1	PMID[482439]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	4.17	ug.mL-1	PMID[482440]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	1.9	ug.mL-1	PMID[482440]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	6.79	ug.mL-1	PMID[482440]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	7.97	ug.mL-1	PMID[482440]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	1.82	ug.mL-1	PMID[482440]
NPT176	Organism	Artemia salina	Artemia salina	LD50	<	10.0	ppm	PMID[482440]

☑ 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 NPC478084 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	438
0.1-0.2	3459
0.2-0.3	9111
0.3-0.4	15492
0.4-0.5	6405
0.5-0.6	5495
0.6-0.7	2060
0.7-0.8	219
0.8-0.85	13
0.85-0.9	2
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.8611	High Similarity	NPC328304
0.8611	High Similarity	NPC329466
0.8375	Intermediate Similarity	NPC328639
0.8375	Intermediate Similarity	NPC329490
0.8313	Intermediate Similarity	NPC476727
0.8313	Intermediate Similarity	NPC476726
0.8214	Intermediate Similarity	NPC470920
0.8	Intermediate Similarity	NPC263802
0.7952	Intermediate Similarity	NPC269684
0.7952	Intermediate Similarity	NPC227170
0.7882	Intermediate Similarity	NPC475729
0.7882	Intermediate Similarity	NPC248216
0.7882	Intermediate Similarity	NPC474215
0.7867	Intermediate Similarity	NPC472984
0.7857	Intermediate Similarity	NPC475689
0.7848	Intermediate Similarity	NPC159789
0.7778	Intermediate Similarity	NPC475725
0.7738	Intermediate Similarity	NPC327451
0.7701	Intermediate Similarity	NPC236459
0.7683	Intermediate Similarity	NPC275243
0.7674	Intermediate Similarity	NPC472272
0.7674	Intermediate Similarity	NPC80700
0.7667	Intermediate Similarity	NPC478089
0.7647	Intermediate Similarity	NPC50438
0.7619	Intermediate Similarity	NPC121121
0.7595	Intermediate Similarity	NPC81759
0.75	Intermediate Similarity	NPC476071
0.75	Intermediate Similarity	NPC477264
0.7473	Intermediate Similarity	NPC247877
0.7473	Intermediate Similarity	NPC309127
0.7471	Intermediate Similarity	NPC120395
0.7436	Intermediate Similarity	NPC470833
0.7416	Intermediate Similarity	NPC477440
0.7416	Intermediate Similarity	NPC477443
0.7412	Intermediate Similarity	NPC317066
0.7412	Intermediate Similarity	NPC268040
0.7407	Intermediate Similarity	NPC267753
0.7386	Intermediate Similarity	NPC202937
0.7381	Intermediate Similarity	NPC470609
0.7356	Intermediate Similarity	NPC477205
0.7356	Intermediate Similarity	NPC131350
0.7333	Intermediate Similarity	NPC185529
0.7333	Intermediate Similarity	NPC472146
0.7333	Intermediate Similarity	NPC477442
0.7333	Intermediate Similarity	NPC477433
0.7333	Intermediate Similarity	NPC477444
0.7317	Intermediate Similarity	NPC472487
0.7317	Intermediate Similarity	NPC472486
0.7312	Intermediate Similarity	NPC476728
0.7303	Intermediate Similarity	NPC476379
0.7303	Intermediate Similarity	NPC90676
0.7303	Intermediate Similarity	NPC476435
0.7294	Intermediate Similarity	NPC469745
0.7284	Intermediate Similarity	NPC130011
0.7284	Intermediate Similarity	NPC133922
0.7284	Intermediate Similarity	NPC254340
0.7284	Intermediate Similarity	NPC317212
0.7273	Intermediate Similarity	NPC475276
0.7273	Intermediate Similarity	NPC34190
0.7262	Intermediate Similarity	NPC320144
0.725	Intermediate Similarity	NPC89310
0.7241	Intermediate Similarity	NPC105895
0.7241	Intermediate Similarity	NPC219535
0.7241	Intermediate Similarity	NPC237938
0.7241	Intermediate Similarity	NPC477434
0.7234	Intermediate Similarity	NPC170978
0.7229	Intermediate Similarity	NPC475031
0.7229	Intermediate Similarity	NPC221420
0.7222	Intermediate Similarity	NPC56962
0.7222	Intermediate Similarity	NPC24705
0.7215	Intermediate Similarity	NPC327728
0.7215	Intermediate Similarity	NPC6120
0.7215	Intermediate Similarity	NPC213178
0.7215	Intermediate Similarity	NPC131892
0.7204	Intermediate Similarity	NPC305808
0.7204	Intermediate Similarity	NPC17336
0.7204	Intermediate Similarity	NPC41070
0.7195	Intermediate Similarity	NPC125767
0.7195	Intermediate Similarity	NPC21220
0.7191	Intermediate Similarity	NPC239938
0.7176	Intermediate Similarity	NPC125366
0.7176	Intermediate Similarity	NPC477851
0.7174	Intermediate Similarity	NPC472147
0.7174	Intermediate Similarity	NPC472148
0.716	Intermediate Similarity	NPC282905
0.716	Intermediate Similarity	NPC477229
0.716	Intermediate Similarity	NPC68426
0.716	Intermediate Similarity	NPC232112
0.7159	Intermediate Similarity	NPC477445
0.7158	Intermediate Similarity	NPC253995
0.7143	Intermediate Similarity	NPC80089
0.7143	Intermediate Similarity	NPC475056
0.7143	Intermediate Similarity	NPC34046
0.7143	Intermediate Similarity	NPC185465
0.7143	Intermediate Similarity	NPC476296
0.7143	Intermediate Similarity	NPC26029
0.7143	Intermediate Similarity	NPC324700
0.7143	Intermediate Similarity	NPC136801
0.7143	Intermediate Similarity	NPC224802
0.7143	Intermediate Similarity	NPC171426
0.7128	Intermediate Similarity	NPC260223
0.7126	Intermediate Similarity	NPC15091
0.7113	Intermediate Similarity	NPC471254
0.7111	Intermediate Similarity	NPC477614
0.7111	Intermediate Similarity	NPC226491
0.7108	Intermediate Similarity	NPC108840
0.7108	Intermediate Similarity	NPC475742
0.7108	Intermediate Similarity	NPC5767
0.71	Intermediate Similarity	NPC289702
0.71	Intermediate Similarity	NPC208461
0.7097	Intermediate Similarity	NPC470424
0.7097	Intermediate Similarity	NPC76136
0.7097	Intermediate Similarity	NPC329713
0.7097	Intermediate Similarity	NPC217567
0.7093	Intermediate Similarity	NPC12933
0.7093	Intermediate Similarity	NPC254123
0.7079	Intermediate Similarity	NPC83242
0.7073	Intermediate Similarity	NPC159325
0.7073	Intermediate Similarity	NPC168511
0.7059	Intermediate Similarity	NPC201276
0.7059	Intermediate Similarity	NPC80891
0.7053	Intermediate Similarity	NPC471241
0.7053	Intermediate Similarity	NPC74466
0.7045	Intermediate Similarity	NPC79308
0.7045	Intermediate Similarity	NPC291310
0.7041	Intermediate Similarity	NPC471253
0.7041	Intermediate Similarity	NPC191892
0.7037	Intermediate Similarity	NPC151018
0.7037	Intermediate Similarity	NPC156277
0.7037	Intermediate Similarity	NPC320549
0.7037	Intermediate Similarity	NPC58057
0.7033	Intermediate Similarity	NPC200580
0.7033	Intermediate Similarity	NPC67653
0.7033	Intermediate Similarity	NPC471459
0.7033	Intermediate Similarity	NPC61688
0.7024	Intermediate Similarity	NPC264602
0.7024	Intermediate Similarity	NPC207010
0.7024	Intermediate Similarity	NPC23884
0.7024	Intermediate Similarity	NPC307865
0.7024	Intermediate Similarity	NPC317913
0.7024	Intermediate Similarity	NPC112463
0.7021	Intermediate Similarity	NPC287354
0.7021	Intermediate Similarity	NPC200702
0.7021	Intermediate Similarity	NPC272617
0.7021	Intermediate Similarity	NPC62407
0.7013	Intermediate Similarity	NPC94897
0.7011	Intermediate Similarity	NPC328007
0.701	Intermediate Similarity	NPC298266
0.701	Intermediate Similarity	NPC259654
0.7	Intermediate Similarity	NPC153604
0.6989	Remote Similarity	NPC474379
0.6989	Remote Similarity	NPC472496
0.6988	Remote Similarity	NPC195155
0.6988	Remote Similarity	NPC158208
0.6988	Remote Similarity	NPC174964
0.6988	Remote Similarity	NPC97534
0.6988	Remote Similarity	NPC243027
0.6988	Remote Similarity	NPC196136
0.6988	Remote Similarity	NPC273366
0.6979	Remote Similarity	NPC472144
0.6979	Remote Similarity	NPC476294
0.6966	Remote Similarity	NPC473350
0.6962	Remote Similarity	NPC53879
0.6962	Remote Similarity	NPC57788
0.6957	Remote Similarity	NPC18536
0.6957	Remote Similarity	NPC77756
0.6957	Remote Similarity	NPC100313
0.6957	Remote Similarity	NPC50443
0.6957	Remote Similarity	NPC46758
0.6947	Remote Similarity	NPC475785
0.6947	Remote Similarity	NPC163685
0.6947	Remote Similarity	NPC256227
0.6947	Remote Similarity	NPC235109
0.6947	Remote Similarity	NPC219353
0.6941	Remote Similarity	NPC472608
0.6939	Remote Similarity	NPC470172
0.6932	Remote Similarity	NPC268578
0.6932	Remote Similarity	NPC217559
0.6932	Remote Similarity	NPC472744
0.6932	Remote Similarity	NPC292458
0.6931	Remote Similarity	NPC293850
0.6923	Remote Similarity	NPC131104
0.6923	Remote Similarity	NPC473319
0.6923	Remote Similarity	NPC3032
0.6923	Remote Similarity	NPC158778
0.6915	Remote Similarity	NPC196227
0.6907	Remote Similarity	NPC127408
0.6907	Remote Similarity	NPC291785
0.6907	Remote Similarity	NPC470388
0.6905	Remote Similarity	NPC163597
0.6905	Remote Similarity	NPC4209
0.6905	Remote Similarity	NPC474020
0.69	Remote Similarity	NPC181357
0.6897	Remote Similarity	NPC328264
0.6897	Remote Similarity	NPC475743
0.6893	Remote Similarity	NPC146945
0.6893	Remote Similarity	NPC171888
0.6889	Remote Similarity	NPC302111
0.6889	Remote Similarity	NPC472745
0.6889	Remote Similarity	NPC477441

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 NPC478084 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	515
0.1-0.2	3761
0.2-0.3	3214
0.3-0.4	1073
0.4-0.5	323
0.5-0.6	190
0.6-0.7	61
0.7-0.8	13
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
0.7848	Intermediate Similarity	NPD3703	Phase 2
0.7215	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6115	Approved
0.7143	Intermediate Similarity	NPD6118	Approved
0.7143	Intermediate Similarity	NPD6114	Approved
0.7143	Intermediate Similarity	NPD6697	Approved
0.71	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6116	Phase 1
0.6914	Remote Similarity	NPD4789	Approved
0.6905	Remote Similarity	NPD6117	Approved
0.679	Remote Similarity	NPD3698	Phase 2
0.6709	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4244	Approved
0.6707	Remote Similarity	NPD4245	Approved
0.6701	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD5360	Phase 3
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4634	Approved
0.6585	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD371	Approved
0.6566	Remote Similarity	NPD5286	Approved
0.6566	Remote Similarity	NPD4696	Approved
0.6566	Remote Similarity	NPD5285	Approved
0.6566	Remote Similarity	NPD4700	Approved
0.6552	Remote Similarity	NPD3671	Phase 1
0.65	Remote Similarity	NPD5223	Approved
0.6471	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD4632	Approved
0.6436	Remote Similarity	NPD5224	Approved
0.6436	Remote Similarity	NPD5226	Approved
0.6436	Remote Similarity	NPD5211	Phase 2
0.6436	Remote Similarity	NPD4633	Approved
0.6436	Remote Similarity	NPD5225	Approved
0.6429	Remote Similarity	NPD5222	Approved
0.6429	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5221	Approved
0.6429	Remote Similarity	NPD4697	Phase 3
0.6429	Remote Similarity	NPD4758	Discontinued
0.6395	Remote Similarity	NPD3702	Approved
0.6373	Remote Similarity	NPD5175	Approved
0.6373	Remote Similarity	NPD4754	Approved
0.6373	Remote Similarity	NPD5174	Approved
0.6364	Remote Similarity	NPD5173	Approved
0.6339	Remote Similarity	NPD6921	Approved
0.6337	Remote Similarity	NPD1700	Approved
0.6333	Remote Similarity	NPD1780	Approved
0.6333	Remote Similarity	NPD1779	Approved
0.6316	Remote Similarity	NPD5328	Approved
0.6311	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD6402	Approved
0.625	Remote Similarity	NPD6675	Approved
0.625	Remote Similarity	NPD5739	Approved
0.625	Remote Similarity	NPD7128	Approved
0.625	Remote Similarity	NPD4768	Approved
0.6226	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.622	Remote Similarity	NPD4224	Phase 2
0.619	Remote Similarity	NPD5697	Approved
0.619	Remote Similarity	NPD5701	Approved
0.6186	Remote Similarity	NPD6079	Approved
0.618	Remote Similarity	NPD5364	Discontinued
0.617	Remote Similarity	NPD3618	Phase 1
0.6132	Remote Similarity	NPD6011	Approved
0.6132	Remote Similarity	NPD4729	Approved
0.6132	Remote Similarity	NPD6881	Approved
0.6132	Remote Similarity	NPD5128	Approved
0.6132	Remote Similarity	NPD7320	Approved
0.6132	Remote Similarity	NPD4730	Approved
0.6132	Remote Similarity	NPD6899	Approved
0.6126	Remote Similarity	NPD6009	Approved
0.6126	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4202	Approved
0.6106	Remote Similarity	NPD6319	Approved
0.6092	Remote Similarity	NPD1810	Approved
0.6092	Remote Similarity	NPD1811	Approved
0.6087	Remote Similarity	NPD3667	Approved
0.6075	Remote Similarity	NPD6013	Approved
0.6075	Remote Similarity	NPD6373	Approved
0.6075	Remote Similarity	NPD6014	Approved
0.6075	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6012	Approved
0.6075	Remote Similarity	NPD6372	Approved
0.6064	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD8297	Approved
0.6047	Remote Similarity	NPD6081	Approved
0.6022	Remote Similarity	NPD3669	Approved
0.6022	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7515	Phase 2
0.6019	Remote Similarity	NPD5251	Approved
0.6019	Remote Similarity	NPD5250	Approved
0.6019	Remote Similarity	NPD7102	Approved
0.6019	Remote Similarity	NPD5169	Approved
0.6019	Remote Similarity	NPD5135	Approved
0.6019	Remote Similarity	NPD5248	Approved
0.6019	Remote Similarity	NPD7290	Approved
0.6019	Remote Similarity	NPD5249	Phase 3
0.6019	Remote Similarity	NPD5247	Approved
0.6019	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6883	Approved
0.5979	Remote Similarity	NPD4753	Phase 2
0.5976	Remote Similarity	NPD7909	Approved
0.5965	Remote Similarity	NPD6054	Approved
0.5965	Remote Similarity	NPD6059	Approved
0.5963	Remote Similarity	NPD5216	Approved
0.5963	Remote Similarity	NPD6617	Approved
0.5963	Remote Similarity	NPD5127	Approved
0.5963	Remote Similarity	NPD6650	Approved
0.5963	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5217	Approved
0.5963	Remote Similarity	NPD6847	Approved
0.5963	Remote Similarity	NPD6649	Approved
0.5963	Remote Similarity	NPD6869	Approved
0.5963	Remote Similarity	NPD5215	Approved
0.5963	Remote Similarity	NPD8130	Phase 1
0.5957	Remote Similarity	NPD4786	Approved
0.5948	Remote Similarity	NPD8328	Phase 3
0.5913	Remote Similarity	NPD6015	Approved
0.5913	Remote Similarity	NPD6016	Approved
0.5913	Remote Similarity	NPD5983	Phase 2
0.5909	Remote Similarity	NPD6882	Approved
0.587	Remote Similarity	NPD4695	Discontinued
0.5862	Remote Similarity	NPD5777	Approved
0.5862	Remote Similarity	NPD5988	Approved
0.5862	Remote Similarity	NPD6370	Approved
0.5859	Remote Similarity	NPD8034	Phase 2
0.5859	Remote Similarity	NPD8035	Phase 2
0.5851	Remote Similarity	NPD4788	Approved
0.5844	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5168	Approved
0.5833	Remote Similarity	NPD5279	Phase 3
0.5824	Remote Similarity	NPD3617	Approved
0.5812	Remote Similarity	NPD7604	Phase 2
0.5804	Remote Similarity	NPD5167	Approved
0.5789	Remote Similarity	NPD3133	Approved
0.5789	Remote Similarity	NPD3665	Phase 1
0.5789	Remote Similarity	NPD3666	Approved
0.5769	Remote Similarity	NPD8418	Phase 2
0.5763	Remote Similarity	NPD7492	Approved
0.5752	Remote Similarity	NPD6274	Approved
0.5747	Remote Similarity	NPD4787	Phase 1
0.5743	Remote Similarity	NPD7748	Approved
0.5741	Remote Similarity	NPD6412	Phase 2
0.5728	Remote Similarity	NPD7902	Approved
0.5727	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6336	Discontinued
0.5714	Remote Similarity	NPD6616	Approved
0.5714	Remote Similarity	NPD8133	Approved
0.5702	Remote Similarity	NPD6317	Approved
0.5699	Remote Similarity	NPD6928	Phase 2
0.5699	Remote Similarity	NPD7525	Registered
0.5686	Remote Similarity	NPD5210	Approved
0.5686	Remote Similarity	NPD4629	Approved
0.567	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD8293	Discontinued
0.5667	Remote Similarity	NPD7078	Approved
0.5652	Remote Similarity	NPD6314	Approved
0.5652	Remote Similarity	NPD6313	Approved
0.5652	Remote Similarity	NPD6335	Approved
0.5648	Remote Similarity	NPD6008	Approved
0.5644	Remote Similarity	NPD6399	Phase 3
0.5625	Remote Similarity	NPD3668	Phase 3
0.5625	Remote Similarity	NPD4197	Approved
0.562	Remote Similarity	NPD6033	Approved
0.562	Remote Similarity	NPD7736	Approved
0.5612	Remote Similarity	NPD3573	Approved
0.5603	Remote Similarity	NPD7100	Approved
0.5603	Remote Similarity	NPD7101	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