NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	522.22
Volume:	548.28
LogP:	5.684
LogD:	2.782
LogS:	-3.788
# Rotatable Bonds:	6
TPSA:	120.09
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.188
Synthetic Accessibility Score:	3.485
Fsp3:	0.25
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.039
MDCK Permeability:	8.28467273095157e-06
Pgp-inhibitor:	0.779
Pgp-substrate:	0.96
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.89
30% Bioavailability (F30%):	0.085

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	94.17742156982422%
Volume Distribution (VD):	0.594
Pgp-substrate:	1.7868645191192627%

ADMET: Metabolism

CYP1A2-inhibitor:	0.187
CYP1A2-substrate:	0.126
CYP2C19-inhibitor:	0.89
CYP2C19-substrate:	0.384
CYP2C9-inhibitor:	0.881
CYP2C9-substrate:	0.917
CYP2D6-inhibitor:	0.685
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.932
CYP3A4-substrate:	0.448

ADMET: Excretion

Clearance (CL):	1.324
Half-life (T1/2):	0.196

ADMET: Toxicity

hERG Blockers:	0.117
Human Hepatotoxicity (H-HT):	0.95
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.907
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.187
Carcinogencity:	0.048
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.039

Download Data

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

Natural Product: NPC476818

Natural Product ID:	NPC476818
*Common Name:**	Chaetoglobinol A
IUPAC Name:	3,5-dihydroxy-3,6-bis[5-(3-methylbut-2-enyl)-1H-indol-3-yl]cyclohex-5-ene-1,2,4-trione
Synonyms:
Standard InCHIKey:	QOAPGRJTTCYFMV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C32H30N2O5/c1-17(2)5-7-19-9-11-25-21(13-19)23(15-33-25)27-28(35)30(37)32(39,31(38)29(27)36)24-16-34-26-12-10-20(14-22(24)26)8-6-18(3)4/h5-6,9-16,33-35,39H,7-8H2,1-4H3
SMILES:	CC(=CCC1=CC2=C(C=C1)NC=C2C3=C(C(=O)C(C(=O)C3=O)(C4=CNC5=C4C=C(C=C5)CC=C(C)C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122181663
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12357398]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12483566]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497948]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921417]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209910]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499339]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872138]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16904330]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125234]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17827664]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	Ginkgo biloba	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19427327]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20225834]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20814854]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	isolated from the leaves of Viguiera robusta	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21640594]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854043]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22112725]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22593034]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23072467]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	Xichang of Sichuan Province, China	n.a.	PMID[26125976]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26343828]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5066072]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7116505]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[CiteXplore Id]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	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	2
MIC	2
Others	1

Activity Type	# Activity
Organism	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		Inhibition	=	30.4	%	PMID[26125976]
NPT1	Others	Radical scavenging activity		IC50	=	45200	nM	PMID[26125976]
NPT1	Others	Radical scavenging activity		IC50	=	143600	nM	PMID[26125976]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	50	ug/ml	PMID[26125976]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	50	ug/ml	PMID[26125976]

☑ 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 NPC476818 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	395
0.1-0.2	2378
0.2-0.3	10907
0.3-0.4	14381
0.4-0.5	10095
0.5-0.6	1967
0.6-0.7	2135
0.7-0.8	425
0.8-0.85	10
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8744	High Similarity	NPC227582
0.8706	High Similarity	NPC252338
0.8473	Intermediate Similarity	NPC74413
0.835	Intermediate Similarity	NPC260900
0.8263	Intermediate Similarity	NPC474412
0.8244	Intermediate Similarity	NPC131887
0.8157	Intermediate Similarity	NPC276657
0.8148	Intermediate Similarity	NPC264285
0.8082	Intermediate Similarity	NPC16352
0.8066	Intermediate Similarity	NPC258062
0.8056	Intermediate Similarity	NPC203614
0.8019	Intermediate Similarity	NPC225821
0.8	Intermediate Similarity	NPC87856
0.7972	Intermediate Similarity	NPC132211
0.7964	Intermediate Similarity	NPC147446
0.7953	Intermediate Similarity	NPC82370
0.7944	Intermediate Similarity	NPC271862
0.7928	Intermediate Similarity	NPC141428
0.7897	Intermediate Similarity	NPC127677
0.7895	Intermediate Similarity	NPC67288
0.789	Intermediate Similarity	NPC204491
0.7885	Intermediate Similarity	NPC11445
0.788	Intermediate Similarity	NPC267965
0.7877	Intermediate Similarity	NPC98715
0.7857	Intermediate Similarity	NPC57690
0.7854	Intermediate Similarity	NPC472285
0.785	Intermediate Similarity	NPC46225
0.7837	Intermediate Similarity	NPC195239
0.7837	Intermediate Similarity	NPC157828
0.7834	Intermediate Similarity	NPC110182
0.7834	Intermediate Similarity	NPC151976
0.783	Intermediate Similarity	NPC476073
0.7816	Intermediate Similarity	NPC83111
0.7803	Intermediate Similarity	NPC229893
0.7768	Intermediate Similarity	NPC235885
0.7767	Intermediate Similarity	NPC321708
0.7735	Intermediate Similarity	NPC178858
0.7723	Intermediate Similarity	NPC55772
0.7713	Intermediate Similarity	NPC2395
0.7686	Intermediate Similarity	NPC70155
0.7675	Intermediate Similarity	NPC290529
0.7664	Intermediate Similarity	NPC193761
0.7655	Intermediate Similarity	NPC267926
0.7647	Intermediate Similarity	NPC36405
0.7644	Intermediate Similarity	NPC266192
0.7642	Intermediate Similarity	NPC207686
0.7639	Intermediate Similarity	NPC175602
0.7636	Intermediate Similarity	NPC31700
0.7632	Intermediate Similarity	NPC326363
0.7623	Intermediate Similarity	NPC269270
0.7615	Intermediate Similarity	NPC61038
0.7589	Intermediate Similarity	NPC14686
0.7586	Intermediate Similarity	NPC111275
0.7586	Intermediate Similarity	NPC15801
0.7576	Intermediate Similarity	NPC325976
0.7571	Intermediate Similarity	NPC47190
0.757	Intermediate Similarity	NPC213308
0.756	Intermediate Similarity	NPC154339
0.7548	Intermediate Similarity	NPC278434
0.7542	Intermediate Similarity	NPC78609
0.7536	Intermediate Similarity	NPC267343
0.7523	Intermediate Similarity	NPC478157
0.7511	Intermediate Similarity	NPC219087
0.75	Intermediate Similarity	NPC303951
0.75	Intermediate Similarity	NPC473310
0.75	Intermediate Similarity	NPC235684
0.75	Intermediate Similarity	NPC59269
0.7489	Intermediate Similarity	NPC63031
0.7489	Intermediate Similarity	NPC132329
0.7488	Intermediate Similarity	NPC99666
0.7477	Intermediate Similarity	NPC207866
0.7467	Intermediate Similarity	NPC476491
0.7466	Intermediate Similarity	NPC23294
0.7455	Intermediate Similarity	NPC27041
0.7454	Intermediate Similarity	NPC300183
0.7448	Intermediate Similarity	NPC63971
0.7448	Intermediate Similarity	NPC91868
0.7441	Intermediate Similarity	NPC476460
0.743	Intermediate Similarity	NPC156704
0.7421	Intermediate Similarity	NPC234999
0.7419	Intermediate Similarity	NPC476874
0.7418	Intermediate Similarity	NPC202812
0.7416	Intermediate Similarity	NPC315555
0.7407	Intermediate Similarity	NPC315491
0.7407	Intermediate Similarity	NPC45459
0.7406	Intermediate Similarity	NPC107836
0.7404	Intermediate Similarity	NPC41679
0.7387	Intermediate Similarity	NPC131718
0.7379	Intermediate Similarity	NPC213468
0.7376	Intermediate Similarity	NPC78020
0.7376	Intermediate Similarity	NPC478158
0.7371	Intermediate Similarity	NPC304203
0.7368	Intermediate Similarity	NPC15102
0.7366	Intermediate Similarity	NPC267885
0.7364	Intermediate Similarity	NPC88008
0.7354	Intermediate Similarity	NPC475778
0.7352	Intermediate Similarity	NPC477043
0.7339	Intermediate Similarity	NPC328318
0.7339	Intermediate Similarity	NPC328596
0.7337	Intermediate Similarity	NPC135141
0.7337	Intermediate Similarity	NPC92796
0.7333	Intermediate Similarity	NPC62749
0.7331	Intermediate Similarity	NPC101350
0.733	Intermediate Similarity	NPC171787
0.733	Intermediate Similarity	NPC314957
0.733	Intermediate Similarity	NPC86834
0.733	Intermediate Similarity	NPC210828
0.7325	Intermediate Similarity	NPC473317
0.7319	Intermediate Similarity	NPC473187
0.7317	Intermediate Similarity	NPC203468
0.7317	Intermediate Similarity	NPC110500
0.7317	Intermediate Similarity	NPC149155
0.7299	Intermediate Similarity	NPC46580
0.7297	Intermediate Similarity	NPC162860
0.7295	Intermediate Similarity	NPC126709
0.7295	Intermediate Similarity	NPC248041
0.7295	Intermediate Similarity	NPC283219
0.7291	Intermediate Similarity	NPC63751
0.7288	Intermediate Similarity	NPC235685
0.7286	Intermediate Similarity	NPC308931
0.7286	Intermediate Similarity	NPC314002
0.7286	Intermediate Similarity	NPC99939
0.7285	Intermediate Similarity	NPC54420
0.7285	Intermediate Similarity	NPC183777
0.7284	Intermediate Similarity	NPC471536
0.7281	Intermediate Similarity	NPC293917
0.728	Intermediate Similarity	NPC477107
0.728	Intermediate Similarity	NPC477109
0.728	Intermediate Similarity	NPC477108
0.7277	Intermediate Similarity	NPC75634
0.7277	Intermediate Similarity	NPC138370
0.7273	Intermediate Similarity	NPC24370
0.7273	Intermediate Similarity	NPC319232
0.7269	Intermediate Similarity	NPC77555
0.7269	Intermediate Similarity	NPC477714
0.7268	Intermediate Similarity	NPC313791
0.7257	Intermediate Similarity	NPC3207
0.7252	Intermediate Similarity	NPC39679
0.7251	Intermediate Similarity	NPC171171
0.7251	Intermediate Similarity	NPC160381
0.7249	Intermediate Similarity	NPC60621
0.7248	Intermediate Similarity	NPC214428
0.7246	Intermediate Similarity	NPC151939
0.7246	Intermediate Similarity	NPC284775
0.7244	Intermediate Similarity	NPC229348
0.7243	Intermediate Similarity	NPC324149
0.724	Intermediate Similarity	NPC317373
0.7238	Intermediate Similarity	NPC201831
0.7238	Intermediate Similarity	NPC204717
0.7238	Intermediate Similarity	NPC473312
0.7238	Intermediate Similarity	NPC17487
0.7237	Intermediate Similarity	NPC74360
0.7235	Intermediate Similarity	NPC149708
0.7235	Intermediate Similarity	NPC102008
0.7234	Intermediate Similarity	NPC323752
0.7232	Intermediate Similarity	NPC9894
0.723	Intermediate Similarity	NPC95783
0.7229	Intermediate Similarity	NPC125597
0.7228	Intermediate Similarity	NPC102423
0.7225	Intermediate Similarity	NPC477715
0.7222	Intermediate Similarity	NPC267853
0.7217	Intermediate Similarity	NPC17059
0.7215	Intermediate Similarity	NPC475506
0.7213	Intermediate Similarity	NPC153400
0.7212	Intermediate Similarity	NPC237740
0.721	Intermediate Similarity	NPC33949
0.7205	Intermediate Similarity	NPC272174
0.7205	Intermediate Similarity	NPC150239
0.7205	Intermediate Similarity	NPC174760
0.7204	Intermediate Similarity	NPC280290
0.7203	Intermediate Similarity	NPC39370
0.72	Intermediate Similarity	NPC207020
0.7195	Intermediate Similarity	NPC327592
0.7195	Intermediate Similarity	NPC475070
0.7191	Intermediate Similarity	NPC244897
0.719	Intermediate Similarity	NPC220765
0.7189	Intermediate Similarity	NPC74153
0.7184	Intermediate Similarity	NPC314603
0.7183	Intermediate Similarity	NPC213629
0.7183	Intermediate Similarity	NPC221873
0.7182	Intermediate Similarity	NPC474116
0.7182	Intermediate Similarity	NPC155143
0.7181	Intermediate Similarity	NPC322064
0.7181	Intermediate Similarity	NPC170114
0.7179	Intermediate Similarity	NPC472844
0.7178	Intermediate Similarity	NPC160898
0.7178	Intermediate Similarity	NPC208522
0.7176	Intermediate Similarity	NPC195314
0.7174	Intermediate Similarity	NPC474896
0.7173	Intermediate Similarity	NPC477549
0.7172	Intermediate Similarity	NPC14812
0.717	Intermediate Similarity	NPC99428
0.7168	Intermediate Similarity	NPC317752
0.7163	Intermediate Similarity	NPC84827
0.7163	Intermediate Similarity	NPC14113
0.7163	Intermediate Similarity	NPC145885
0.7157	Intermediate Similarity	NPC160105
0.7157	Intermediate Similarity	NPC49954
0.7157	Intermediate Similarity	NPC474561
0.7156	Intermediate Similarity	NPC473640

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 NPC476818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	605
0.2-0.3	725
0.3-0.4	1888
0.4-0.5	2813
0.5-0.6	1988
0.6-0.7	789
0.7-0.8	98
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8182	Intermediate Similarity	NPD5901	Discontinued
0.8095	Intermediate Similarity	NPD5426	Phase 3
0.7773	Intermediate Similarity	NPD6999	Discontinued
0.7773	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6987	Phase 1
0.7671	Intermediate Similarity	NPD8093	Discontinued
0.7639	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD7001	Phase 3
0.7636	Intermediate Similarity	NPD8094	Discontinued
0.7621	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD7948	Phase 1
0.758	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD2091	Phase 2
0.7573	Intermediate Similarity	NPD2096	Phase 2
0.7569	Intermediate Similarity	NPD7666	Phase 3
0.7569	Intermediate Similarity	NPD7665	Phase 2
0.7545	Intermediate Similarity	NPD7470	Discontinued
0.7524	Intermediate Similarity	NPD2094	Phase 2
0.7524	Intermediate Similarity	NPD2092	Phase 2
0.7524	Intermediate Similarity	NPD2095	Phase 2
0.7511	Intermediate Similarity	NPD4852	Phase 2
0.7477	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6531	Approved
0.7459	Intermediate Similarity	NPD6530	Approved
0.7457	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD6995	Phase 1
0.7443	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6595	Phase 3
0.7409	Intermediate Similarity	NPD2509	Approved
0.7409	Intermediate Similarity	NPD2510	Approved
0.7407	Intermediate Similarity	NPD484	Approved
0.7404	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD5065	Approved
0.7381	Intermediate Similarity	NPD8431	Approved
0.7371	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD6242	Discontinued
0.734	Intermediate Similarity	NPD1325	Approved
0.734	Intermediate Similarity	NPD1326	Approved
0.7317	Intermediate Similarity	NPD482	Approved
0.7316	Intermediate Similarity	NPD6165	Phase 2
0.7316	Intermediate Similarity	NPD6164	Phase 2
0.7309	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7603	Discontinued
0.7269	Intermediate Similarity	NPD7878	Phase 2
0.7269	Intermediate Similarity	NPD5003	Discontinued
0.7252	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD3404	Approved
0.7241	Intermediate Similarity	NPD4845	Discontinued
0.7238	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7778	Approved
0.7235	Intermediate Similarity	NPD7777	Approved
0.7235	Intermediate Similarity	NPD53	Approved
0.7217	Intermediate Similarity	NPD4948	Discontinued
0.7207	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8073	Approved
0.7169	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7957	Phase 1
0.7162	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD7688	Phase 1
0.7137	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD8097	Phase 3
0.7124	Intermediate Similarity	NPD8096	Phase 3
0.7123	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD2844	Phase 3
0.7117	Intermediate Similarity	NPD8098	Approved
0.7117	Intermediate Similarity	NPD3947	Discontinued
0.7116	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3393	Approved
0.7105	Intermediate Similarity	NPD3394	Approved
0.7105	Intermediate Similarity	NPD3389	Approved
0.7101	Intermediate Similarity	NPD750	Phase 2
0.7095	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7790	Approved
0.7089	Intermediate Similarity	NPD7952	Approved
0.7089	Intermediate Similarity	NPD7950	Approved
0.7089	Intermediate Similarity	NPD7791	Approved
0.7089	Intermediate Similarity	NPD7953	Approved
0.7089	Intermediate Similarity	NPD7951	Approved
0.7089	Intermediate Similarity	NPD7789	Approved
0.7087	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD4886	Phase 2
0.707	Intermediate Similarity	NPD2564	Approved
0.707	Intermediate Similarity	NPD2565	Phase 2
0.7062	Intermediate Similarity	NPD3178	Discontinued
0.7048	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7046	Intermediate Similarity	NPD3746	Discontinued
0.7037	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7731	Approved
0.7021	Intermediate Similarity	NPD7730	Approved
0.7018	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7944	Discontinued
0.7014	Intermediate Similarity	NPD4600	Approved
0.7014	Intermediate Similarity	NPD4601	Approved
0.6996	Remote Similarity	NPD8072	Approved
0.6992	Remote Similarity	NPD7781	Approved
0.6992	Remote Similarity	NPD7780	Approved
0.6983	Remote Similarity	NPD6790	Phase 1
0.6974	Remote Similarity	NPD3330	Phase 1
0.6972	Remote Similarity	NPD1038	Approved
0.6972	Remote Similarity	NPD802	Phase 2
0.6964	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7824	Approved
0.6959	Remote Similarity	NPD2336	Approved
0.6959	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6733	Discontinued
0.6947	Remote Similarity	NPD2916	Discontinued
0.6943	Remote Similarity	NPD3794	Approved
0.6943	Remote Similarity	NPD3795	Approved
0.6936	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7271	Approved
0.6926	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5482	Discontinued
0.6919	Remote Similarity	NPD2144	Approved
0.6909	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7711	Discontinued
0.6906	Remote Similarity	NPD4511	Phase 1
0.6897	Remote Similarity	NPD7181	Phase 3
0.6889	Remote Similarity	NPD8283	Approved
0.6889	Remote Similarity	NPD8282	Approved
0.6889	Remote Similarity	NPD56	Approved
0.6887	Remote Similarity	NPD4079	Approved
0.6887	Remote Similarity	NPD4076	Approved
0.6884	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD5612	Discontinued
0.6878	Remote Similarity	NPD6664	Approved
0.6875	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2172	Phase 1
0.6858	Remote Similarity	NPD7010	Phase 3
0.6853	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2813	Phase 3
0.6853	Remote Similarity	NPD5818	Discontinued
0.6852	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6665	Discontinued
0.6847	Remote Similarity	NPD7946	Pre-registration
0.6844	Remote Similarity	NPD2920	Discontinued
0.684	Remote Similarity	NPD3506	Approved
0.684	Remote Similarity	NPD3505	Approved
0.6835	Remote Similarity	NPD4499	Approved
0.6833	Remote Similarity	NPD2307	Discontinued
0.6833	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2411	Approved
0.6824	Remote Similarity	NPD6456	Discontinued
0.6822	Remote Similarity	NPD3038	Discontinued
0.682	Remote Similarity	NPD8427	Approved
0.682	Remote Similarity	NPD8465	Approved
0.682	Remote Similarity	NPD8429	Approved
0.682	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.682	Remote Similarity	NPD8467	Approved
0.682	Remote Similarity	NPD8428	Approved
0.682	Remote Similarity	NPD8466	Approved
0.6818	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD276	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6376	Discontinued
0.6797	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5100	Phase 3
0.6787	Remote Similarity	NPD7619	Phase 3
0.6787	Remote Similarity	NPD7618	Phase 3
0.6787	Remote Similarity	NPD3809	Discontinued
0.6787	Remote Similarity	NPD7769	Phase 3
0.6784	Remote Similarity	NPD2008	Discontinued
0.6782	Remote Similarity	NPD4463	Approved
0.6782	Remote Similarity	NPD4462	Approved
0.6776	Remote Similarity	NPD7576	Discontinued
0.6771	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7941	Phase 3
0.6769	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD7970	Approved
0.6765	Remote Similarity	NPD8289	Discontinued
0.6763	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7921	Approved
0.6759	Remote Similarity	NPD8091	Phase 3
0.6751	Remote Similarity	NPD3222	Phase 2
0.6748	Remote Similarity	NPD7770	Phase 3
0.6748	Remote Similarity	NPD7860	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD8395	Approved
0.6741	Remote Similarity	NPD8396	Approved
0.674	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3014	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