NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	422.21
Volume:	446.886
LogP:	6.684
LogD:	4.494
LogS:	-3.042
# Rotatable Bonds:	6
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.563
Synthetic Accessibility Score:	3.939
Fsp3:	0.385
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.876
MDCK Permeability:	1.5656718460377306e-05
Pgp-inhibitor:	0.307
Pgp-substrate:	0.159
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.755
30% Bioavailability (F30%):	0.04

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	98.39030456542969%
Volume Distribution (VD):	0.769
Pgp-substrate:	1.9559671878814697%

ADMET: Metabolism

CYP1A2-inhibitor:	0.352
CYP1A2-substrate:	0.921
CYP2C19-inhibitor:	0.96
CYP2C19-substrate:	0.608
CYP2C9-inhibitor:	0.931
CYP2C9-substrate:	0.98
CYP2D6-inhibitor:	0.874
CYP2D6-substrate:	0.88
CYP3A4-inhibitor:	0.652
CYP3A4-substrate:	0.445

ADMET: Excretion

Clearance (CL):	6.232
Half-life (T1/2):	0.188

ADMET: Toxicity

hERG Blockers:	0.074
Human Hepatotoxicity (H-HT):	0.91
Drug-inuced Liver Injury (DILI):	0.361
AMES Toxicity:	0.151
Rat Oral Acute Toxicity:	0.364
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.923
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.739
Respiratory Toxicity:	0.635

Download Data

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

Natural Product: NPC207885

Natural Product ID:	NPC207885
*Common Name:**	Xylarenone A
IUPAC Name:	(1aR,4R,7S,7aR,7bR)-4-hydroxy-1a-(3-hydroxyprop-1-en-2-yl)-7,7a-dimethyl-5,6,7,7b-tetrahydro-4H-naphtho[1,2-b]oxiren-2-one
Synonyms:	Xylarenone A
Standard InCHIKey:	PSGJCHLXOJTCGB-SXHPEXCUSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-8-4-5-11(17)10-6-12(18)15(9(2)7-16)13(19-15)14(8,10)3/h6,8,11,13,16-17H,2,4-5,7H2,1,3H3/t8-,11+,13+,14+,15-/m0/s1
SMILES:	C[C@H]1CC[C@H](C2=CC(=O)[C@@]3(C(=C)CO)[C@@H]([C@]12C)O3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1813182
PubChem CID:	24752810
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO30237	Xylaria	Genus	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(99)01878-X]
NPO30237	Xylaria	Genus	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17978529]
NPO30237	Xylaria	Genus	Xylariaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21226484]
NPO30237	Xylaria	Genus	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21226484]
NPO30237	Xylaria	Genus	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21428374]
NPO30237	Xylaria	Genus	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21510613]
NPO30643	Endophytic fungi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21510613]
NPO30643	Endophytic fungi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21954864]
NPO30643	Endophytic fungi	n.a.	n.a.	n.a.	n.a.	Costa Rican	n.a.	PMID[22910038]

☑ 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
Others	4

Activity Type	# Activity
Individual Protein	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT620	Individual Protein	Subtilisin/kexin type 7	Homo sapiens	Inhibition	<	10.0	%	PMID[505867]
NPT2	Others	Unspecified		IC50	=	2430.0	nM	PMID[505867]

☑ 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 NPC207885 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	221
0.1-0.2	1314
0.2-0.3	4222
0.3-0.4	7527
0.4-0.5	14687
0.5-0.6	8077
0.6-0.7	5506
0.7-0.8	1107
0.8-0.85	24
0.85-0.9	5
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9787	High Similarity	NPC112613
0.9468	High Similarity	NPC471916
0.9394	High Similarity	NPC322903
0.9362	High Similarity	NPC94337
0.9118	High Similarity	NPC317107
0.9029	High Similarity	NPC317687
0.899	High Similarity	NPC131366
0.8922	High Similarity	NPC87335
0.8889	High Similarity	NPC478176
0.8586	High Similarity	NPC264378
0.8411	Intermediate Similarity	NPC159333
0.8283	Intermediate Similarity	NPC476245
0.8252	Intermediate Similarity	NPC473624
0.8191	Intermediate Similarity	NPC60951
0.8182	Intermediate Similarity	NPC196227
0.8165	Intermediate Similarity	NPC238667
0.8163	Intermediate Similarity	NPC116726
0.8155	Intermediate Similarity	NPC39996
0.8113	Intermediate Similarity	NPC151393
0.81	Intermediate Similarity	NPC316215
0.8095	Intermediate Similarity	NPC1679
0.8091	Intermediate Similarity	NPC270478
0.8061	Intermediate Similarity	NPC473099
0.8061	Intermediate Similarity	NPC134321
0.8056	Intermediate Similarity	NPC207689
0.8039	Intermediate Similarity	NPC316598
0.802	Intermediate Similarity	NPC202833
0.8018	Intermediate Similarity	NPC243065
0.8018	Intermediate Similarity	NPC469684
0.8018	Intermediate Similarity	NPC474518
0.8	Intermediate Similarity	NPC296950
0.8	Intermediate Similarity	NPC72255
0.7981	Intermediate Similarity	NPC476081
0.7981	Intermediate Similarity	NPC137430
0.798	Intermediate Similarity	NPC73457
0.7963	Intermediate Similarity	NPC115257
0.7963	Intermediate Similarity	NPC161816
0.7961	Intermediate Similarity	NPC472644
0.7959	Intermediate Similarity	NPC473100
0.7944	Intermediate Similarity	NPC476479
0.7941	Intermediate Similarity	NPC287668
0.7925	Intermediate Similarity	NPC472645
0.7917	Intermediate Similarity	NPC15807
0.7909	Intermediate Similarity	NPC122056
0.7905	Intermediate Similarity	NPC249187
0.7905	Intermediate Similarity	NPC247957
0.7905	Intermediate Similarity	NPC159533
0.7905	Intermediate Similarity	NPC99266
0.7905	Intermediate Similarity	NPC8196
0.7895	Intermediate Similarity	NPC67569
0.7885	Intermediate Similarity	NPC470184
0.7885	Intermediate Similarity	NPC472643
0.7879	Intermediate Similarity	NPC128672
0.7879	Intermediate Similarity	NPC477684
0.787	Intermediate Similarity	NPC20192
0.787	Intermediate Similarity	NPC475922
0.787	Intermediate Similarity	NPC77089
0.7864	Intermediate Similarity	NPC216478
0.785	Intermediate Similarity	NPC266514
0.785	Intermediate Similarity	NPC67321
0.785	Intermediate Similarity	NPC187435
0.785	Intermediate Similarity	NPC143609
0.7835	Intermediate Similarity	NPC202394
0.7835	Intermediate Similarity	NPC255143
0.783	Intermediate Similarity	NPC146731
0.783	Intermediate Similarity	NPC258532
0.7826	Intermediate Similarity	NPC23786
0.7826	Intermediate Similarity	NPC470265
0.7822	Intermediate Similarity	NPC470697
0.7822	Intermediate Similarity	NPC217624
0.7822	Intermediate Similarity	NPC181393
0.7818	Intermediate Similarity	NPC473877
0.781	Intermediate Similarity	NPC469606
0.781	Intermediate Similarity	NPC273005
0.781	Intermediate Similarity	NPC31058
0.78	Intermediate Similarity	NPC475441
0.7798	Intermediate Similarity	NPC5103
0.7789	Intermediate Similarity	NPC47450
0.7789	Intermediate Similarity	NPC93590
0.7788	Intermediate Similarity	NPC472972
0.7788	Intermediate Similarity	NPC251310
0.7788	Intermediate Similarity	NPC186525
0.7788	Intermediate Similarity	NPC709
0.7788	Intermediate Similarity	NPC474012
0.7788	Intermediate Similarity	NPC476299
0.7788	Intermediate Similarity	NPC50774
0.7788	Intermediate Similarity	NPC240509
0.7788	Intermediate Similarity	NPC469551
0.7778	Intermediate Similarity	NPC472439
0.7778	Intermediate Similarity	NPC233379
0.7778	Intermediate Similarity	NPC14862
0.7778	Intermediate Similarity	NPC264819
0.7778	Intermediate Similarity	NPC225049
0.7778	Intermediate Similarity	NPC474664
0.7778	Intermediate Similarity	NPC469916
0.7767	Intermediate Similarity	NPC70145
0.7767	Intermediate Similarity	NPC91695
0.7767	Intermediate Similarity	NPC205143
0.7766	Intermediate Similarity	NPC172013
0.7759	Intermediate Similarity	NPC469789
0.7759	Intermediate Similarity	NPC67251
0.7757	Intermediate Similarity	NPC284365
0.7757	Intermediate Similarity	NPC475802
0.7757	Intermediate Similarity	NPC32006
0.7757	Intermediate Similarity	NPC128828
0.7757	Intermediate Similarity	NPC123726
0.7757	Intermediate Similarity	NPC166607
0.7757	Intermediate Similarity	NPC85529
0.7757	Intermediate Similarity	NPC111952
0.7757	Intermediate Similarity	NPC257353
0.775	Intermediate Similarity	NPC476193
0.7748	Intermediate Similarity	NPC477266
0.7748	Intermediate Similarity	NPC71889
0.7748	Intermediate Similarity	NPC477126
0.7745	Intermediate Similarity	NPC272617
0.7745	Intermediate Similarity	NPC183012
0.7742	Intermediate Similarity	NPC178852
0.7736	Intermediate Similarity	NPC120321
0.7736	Intermediate Similarity	NPC469980
0.7736	Intermediate Similarity	NPC104161
0.7736	Intermediate Similarity	NPC118902
0.7736	Intermediate Similarity	NPC320154
0.7736	Intermediate Similarity	NPC478057
0.7736	Intermediate Similarity	NPC95899
0.7732	Intermediate Similarity	NPC476678
0.7723	Intermediate Similarity	NPC115021
0.7719	Intermediate Similarity	NPC472933
0.7714	Intermediate Similarity	NPC472637
0.7714	Intermediate Similarity	NPC97435
0.7706	Intermediate Similarity	NPC15218
0.77	Intermediate Similarity	NPC475823
0.77	Intermediate Similarity	NPC113393
0.77	Intermediate Similarity	NPC474209
0.7699	Intermediate Similarity	NPC470493
0.7699	Intermediate Similarity	NPC167606
0.7699	Intermediate Similarity	NPC140055
0.7699	Intermediate Similarity	NPC183580
0.7699	Intermediate Similarity	NPC286528
0.7699	Intermediate Similarity	NPC20302
0.7699	Intermediate Similarity	NPC53396
0.7699	Intermediate Similarity	NPC312824
0.7699	Intermediate Similarity	NPC239273
0.7699	Intermediate Similarity	NPC98249
0.7699	Intermediate Similarity	NPC470492
0.7692	Intermediate Similarity	NPC23364
0.7692	Intermediate Similarity	NPC476729
0.7692	Intermediate Similarity	NPC177232
0.7692	Intermediate Similarity	NPC24651
0.7692	Intermediate Similarity	NPC109556
0.7692	Intermediate Similarity	NPC212465
0.7692	Intermediate Similarity	NPC470922
0.7692	Intermediate Similarity	NPC222303
0.7692	Intermediate Similarity	NPC8374
0.7685	Intermediate Similarity	NPC474421
0.7685	Intermediate Similarity	NPC326994
0.7685	Intermediate Similarity	NPC324327
0.7685	Intermediate Similarity	NPC473165
0.7685	Intermediate Similarity	NPC194620
0.7685	Intermediate Similarity	NPC72813
0.7679	Intermediate Similarity	NPC474872
0.7677	Intermediate Similarity	NPC307298
0.7677	Intermediate Similarity	NPC53454
0.7672	Intermediate Similarity	NPC312833
0.767	Intermediate Similarity	NPC242848
0.767	Intermediate Similarity	NPC134072
0.767	Intermediate Similarity	NPC272411
0.767	Intermediate Similarity	NPC234993
0.7664	Intermediate Similarity	NPC294259
0.7664	Intermediate Similarity	NPC160843
0.7664	Intermediate Similarity	NPC118911
0.766	Intermediate Similarity	NPC281138
0.766	Intermediate Similarity	NPC308038
0.7658	Intermediate Similarity	NPC90952
0.7658	Intermediate Similarity	NPC277769
0.7658	Intermediate Similarity	NPC269530
0.7653	Intermediate Similarity	NPC472985
0.7653	Intermediate Similarity	NPC94666
0.7653	Intermediate Similarity	NPC472986
0.7652	Intermediate Similarity	NPC474370
0.7647	Intermediate Similarity	NPC477712
0.7647	Intermediate Similarity	NPC53685
0.7647	Intermediate Similarity	NPC477713
0.7647	Intermediate Similarity	NPC38830
0.7647	Intermediate Similarity	NPC476859
0.7647	Intermediate Similarity	NPC250075
0.7636	Intermediate Similarity	NPC235014
0.7636	Intermediate Similarity	NPC89408
0.7636	Intermediate Similarity	NPC153036
0.7632	Intermediate Similarity	NPC284707
0.7629	Intermediate Similarity	NPC469809
0.7627	Intermediate Similarity	NPC293112
0.7624	Intermediate Similarity	NPC186363
0.7624	Intermediate Similarity	NPC172101
0.7624	Intermediate Similarity	NPC26865
0.7624	Intermediate Similarity	NPC233345
0.7624	Intermediate Similarity	NPC476705
0.7619	Intermediate Similarity	NPC154072
0.7619	Intermediate Similarity	NPC47024
0.7619	Intermediate Similarity	NPC474718
0.7619	Intermediate Similarity	NPC46761

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 NPC207885 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	1668
0.2-0.3	3687
0.3-0.4	2319
0.4-0.5	852
0.5-0.6	247
0.6-0.7	180
0.7-0.8	5
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
0.7699	Intermediate Similarity	NPD7115	Discovery
0.7476	Intermediate Similarity	NPD5282	Discontinued
0.7358	Intermediate Similarity	NPD4225	Approved
0.7315	Intermediate Similarity	NPD5211	Phase 2
0.7273	Intermediate Similarity	NPD5739	Approved
0.7273	Intermediate Similarity	NPD7128	Approved
0.7273	Intermediate Similarity	NPD6675	Approved
0.7273	Intermediate Similarity	NPD6402	Approved
0.7264	Intermediate Similarity	NPD4755	Approved
0.7232	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6372	Approved
0.7232	Intermediate Similarity	NPD6373	Approved
0.7212	Intermediate Similarity	NPD5779	Approved
0.7212	Intermediate Similarity	NPD5778	Approved
0.7207	Intermediate Similarity	NPD5701	Approved
0.7207	Intermediate Similarity	NPD5697	Approved
0.7182	Intermediate Similarity	NPD5141	Approved
0.7168	Intermediate Similarity	NPD6371	Approved
0.7168	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4634	Approved
0.7143	Intermediate Similarity	NPD6881	Approved
0.7143	Intermediate Similarity	NPD7320	Approved
0.7143	Intermediate Similarity	NPD6899	Approved
0.713	Intermediate Similarity	NPD4700	Approved
0.713	Intermediate Similarity	NPD7639	Approved
0.713	Intermediate Similarity	NPD4696	Approved
0.713	Intermediate Similarity	NPD7640	Approved
0.713	Intermediate Similarity	NPD5286	Approved
0.713	Intermediate Similarity	NPD5285	Approved
0.7129	Intermediate Similarity	NPD3618	Phase 1
0.7105	Intermediate Similarity	NPD6649	Approved
0.7105	Intermediate Similarity	NPD6650	Approved
0.7103	Intermediate Similarity	NPD6083	Phase 2
0.7103	Intermediate Similarity	NPD6084	Phase 2
0.7087	Intermediate Similarity	NPD4753	Phase 2
0.708	Intermediate Similarity	NPD6013	Approved
0.708	Intermediate Similarity	NPD6012	Approved
0.708	Intermediate Similarity	NPD6014	Approved
0.7075	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5695	Phase 3
0.7059	Intermediate Similarity	NPD6319	Approved
0.7059	Intermediate Similarity	NPD6059	Approved
0.7059	Intermediate Similarity	NPD6054	Approved
0.7037	Intermediate Similarity	NPD5696	Approved
0.7037	Intermediate Similarity	NPD7638	Approved
0.703	Intermediate Similarity	NPD1696	Phase 3
0.703	Intermediate Similarity	NPD1694	Approved
0.7019	Intermediate Similarity	NPD6698	Approved
0.7019	Intermediate Similarity	NPD46	Approved
0.7018	Intermediate Similarity	NPD6883	Approved
0.7018	Intermediate Similarity	NPD7102	Approved
0.7018	Intermediate Similarity	NPD7290	Approved
0.7009	Intermediate Similarity	NPD4697	Phase 3
0.7	Intermediate Similarity	NPD5226	Approved
0.7	Intermediate Similarity	NPD6015	Approved
0.7	Intermediate Similarity	NPD6016	Approved
0.7	Intermediate Similarity	NPD4633	Approved
0.7	Intermediate Similarity	NPD5225	Approved
0.7	Intermediate Similarity	NPD5224	Approved
0.6991	Remote Similarity	NPD6011	Approved
0.6991	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6008	Approved
0.6957	Remote Similarity	NPD6617	Approved
0.6957	Remote Similarity	NPD8130	Phase 1
0.6957	Remote Similarity	NPD6869	Approved
0.6957	Remote Similarity	NPD6847	Approved
0.6944	Remote Similarity	NPD7902	Approved
0.6942	Remote Similarity	NPD6370	Approved
0.6942	Remote Similarity	NPD5988	Approved
0.6937	Remote Similarity	NPD5175	Approved
0.6937	Remote Similarity	NPD5174	Approved
0.6916	Remote Similarity	NPD4629	Approved
0.6916	Remote Similarity	NPD5210	Approved
0.6909	Remote Similarity	NPD5223	Approved
0.6909	Remote Similarity	NPD5344	Discontinued
0.6903	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.69	Remote Similarity	NPD3667	Approved
0.6897	Remote Similarity	NPD8297	Approved
0.6897	Remote Similarity	NPD6882	Approved
0.6887	Remote Similarity	NPD6399	Phase 3
0.6887	Remote Similarity	NPD4202	Approved
0.6885	Remote Similarity	NPD8328	Phase 3
0.6869	Remote Similarity	NPD4695	Discontinued
0.6857	Remote Similarity	NPD5785	Approved
0.6852	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5222	Approved
0.6852	Remote Similarity	NPD5221	Approved
0.6829	Remote Similarity	NPD7492	Approved
0.6822	Remote Similarity	NPD7748	Approved
0.6814	Remote Similarity	NPD4768	Approved
0.6814	Remote Similarity	NPD4767	Approved
0.681	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5279	Phase 3
0.6792	Remote Similarity	NPD5693	Phase 1
0.6792	Remote Similarity	NPD6411	Approved
0.6792	Remote Similarity	NPD7515	Phase 2
0.6789	Remote Similarity	NPD5173	Approved
0.6786	Remote Similarity	NPD4754	Approved
0.6774	Remote Similarity	NPD6616	Approved
0.6765	Remote Similarity	NPD3666	Approved
0.6765	Remote Similarity	NPD4786	Approved
0.6765	Remote Similarity	NPD3665	Phase 1
0.6765	Remote Similarity	NPD3133	Approved
0.6762	Remote Similarity	NPD5328	Approved
0.6754	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6274	Approved
0.672	Remote Similarity	NPD8293	Discontinued
0.672	Remote Similarity	NPD7078	Approved
0.67	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4730	Approved
0.6696	Remote Similarity	NPD6686	Approved
0.6696	Remote Similarity	NPD4729	Approved
0.6696	Remote Similarity	NPD5128	Approved
0.6695	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6636	Remote Similarity	NPD6079	Approved
0.6636	Remote Similarity	NPD7637	Suspended
0.6635	Remote Similarity	NPD4519	Discontinued
0.6635	Remote Similarity	NPD4623	Approved
0.6613	Remote Similarity	NPD7604	Phase 2
0.661	Remote Similarity	NPD6053	Discontinued
0.6609	Remote Similarity	NPD6412	Phase 2
0.6604	Remote Similarity	NPD6101	Approved
0.6604	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4197	Approved
0.6585	Remote Similarity	NPD5983	Phase 2
0.6581	Remote Similarity	NPD5247	Approved
0.6581	Remote Similarity	NPD5248	Approved
0.6581	Remote Similarity	NPD5249	Phase 3
0.6581	Remote Similarity	NPD5250	Approved
0.6581	Remote Similarity	NPD5251	Approved
0.6569	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7101	Approved
0.6557	Remote Similarity	NPD7100	Approved
0.6549	Remote Similarity	NPD7632	Discontinued
0.6538	Remote Similarity	NPD5329	Approved
0.6535	Remote Similarity	NPD6033	Approved
0.6529	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6317	Approved
0.6525	Remote Similarity	NPD5216	Approved
0.6525	Remote Similarity	NPD5217	Approved
0.6525	Remote Similarity	NPD5215	Approved
0.6505	Remote Similarity	NPD6695	Phase 3
0.6505	Remote Similarity	NPD6110	Phase 1
0.6484	Remote Similarity	NPD7319	Approved
0.6476	Remote Similarity	NPD4694	Approved
0.6476	Remote Similarity	NPD5690	Phase 2
0.6476	Remote Similarity	NPD5280	Approved
0.6475	Remote Similarity	NPD6313	Approved
0.6475	Remote Similarity	NPD6335	Approved
0.6475	Remote Similarity	NPD6314	Approved
0.6452	Remote Similarity	NPD8515	Approved
0.6452	Remote Similarity	NPD6908	Approved
0.6452	Remote Similarity	NPD8513	Phase 3
0.6452	Remote Similarity	NPD8516	Approved
0.6452	Remote Similarity	NPD8517	Approved
0.6452	Remote Similarity	NPD6909	Approved
0.6449	Remote Similarity	NPD6904	Approved
0.6449	Remote Similarity	NPD6673	Approved
0.6449	Remote Similarity	NPD1695	Approved
0.6449	Remote Similarity	NPD6080	Approved
0.6442	Remote Similarity	NPD3668	Phase 3
0.6441	Remote Similarity	NPD5135	Approved
0.6441	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5169	Approved
0.6423	Remote Similarity	NPD4522	Approved
0.6408	Remote Similarity	NPD4221	Approved
0.6408	Remote Similarity	NPD4223	Phase 3
0.6389	Remote Similarity	NPD5692	Phase 3
0.6389	Remote Similarity	NPD7838	Discovery
0.6387	Remote Similarity	NPD5127	Approved
0.6387	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5363	Approved
0.6378	Remote Similarity	NPD6336	Discontinued
0.6378	Remote Similarity	NPD7507	Approved
0.6337	Remote Similarity	NPD3617	Approved
0.633	Remote Similarity	NPD5284	Approved
0.633	Remote Similarity	NPD7983	Approved
0.633	Remote Similarity	NPD6050	Approved
0.633	Remote Similarity	NPD5281	Approved
0.633	Remote Similarity	NPD5694	Approved
0.6321	Remote Similarity	NPD7521	Approved
0.6321	Remote Similarity	NPD5330	Approved
0.6321	Remote Similarity	NPD7334	Approved
0.6321	Remote Similarity	NPD7146	Approved
0.6321	Remote Similarity	NPD6409	Approved
0.6321	Remote Similarity	NPD6684	Approved
0.632	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.632	Remote Similarity	NPD6921	Approved
0.6311	Remote Similarity	NPD6868	Approved
0.6308	Remote Similarity	NPD5956	Approved
0.6306	Remote Similarity	NPD6356	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