NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	176.08
Volume:	188.734
LogP:	2.721
LogD:	2.51
LogS:	-2.282
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.509
Synthetic Accessibility Score:	3.372
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.606
MDCK Permeability:	1.900332426885143e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.935
30% Bioavailability (F30%):	0.089

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	83.4648208618164%
Volume Distribution (VD):	0.666
Pgp-substrate:	8.474902153015137%

ADMET: Metabolism

CYP1A2-inhibitor:	0.248
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.126
CYP2C19-substrate:	0.622
CYP2C9-inhibitor:	0.247
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.131
CYP2D6-substrate:	0.843
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.402

ADMET: Excretion

Clearance (CL):	14.202
Half-life (T1/2):	0.746

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.22
Drug-inuced Liver Injury (DILI):	0.071
AMES Toxicity:	0.264
Rat Oral Acute Toxicity:	0.757
Maximum Recommended Daily Dose:	0.87
Skin Sensitization:	0.768
Carcinogencity:	0.567
Eye Corrosion:	0.027
Eye Irritation:	0.877
Respiratory Toxicity:	0.906

Download Data

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

Natural Product: NPC475580

Natural Product ID:	NPC475580
*Common Name:**	Acremonin A
IUPAC Name:	7-prop-1-en-2-ylbicyclo[4.2.0]octa-1,3,5-triene-2,5-diol
Synonyms:
Standard InCHIKey:	CHBOVVKYCNAZHG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H12O2/c1-6(2)7-5-8-9(12)3-4-10(13)11(7)8/h3-4,7,12-13H,1,5H2,2H3
SMILES:	CC(=C)C1CC2=C(C=CC(=C12)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508599
PubChem CID:	10397307
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*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	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[12444684]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[16441074]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	Australian	n.a.	PMID[18288804]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[19199645]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	Mangrove Rhizophora apiculata	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[25689430]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[26928174]

☑ 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
Others	7

Activity Type	# Activity
NON-MOLECULAR	2
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	13.9	%	PMID[476388]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	35.5	%	PMID[476388]
NPT1	Others	Radical scavenging activity		Activity	=	26.0	%	PMID[476388]
NPT1	Others	Radical scavenging activity		Activity	=	85.5	%	PMID[476388]
NPT1	Others	Radical scavenging activity		Activity	=	90.0	%	PMID[476388]
NPT1	Others	Radical scavenging activity		Activity	=	90.1	%	PMID[476388]

☑ 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 NPC475580 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	272
0.1-0.2	1881
0.2-0.3	4923
0.3-0.4	13717
0.4-0.5	6215
0.5-0.6	10256
0.6-0.7	4148
0.7-0.8	997
0.8-0.85	190
0.85-0.9	73
0.9-0.95	24
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.92	High Similarity	NPC272029
0.9192	High Similarity	NPC12221
0.9167	High Similarity	NPC245187
0.9118	High Similarity	NPC320439
0.91	High Similarity	NPC233827
0.9091	High Similarity	NPC48730
0.9091	High Similarity	NPC129373
0.9091	High Similarity	NPC248396
0.9082	High Similarity	NPC152097
0.9062	High Similarity	NPC29373
0.899	High Similarity	NPC260775
0.898	High Similarity	NPC312132
0.898	High Similarity	NPC259512
0.8922	High Similarity	NPC47284
0.8911	High Similarity	NPC108497
0.8911	High Similarity	NPC269212
0.89	High Similarity	NPC72729
0.89	High Similarity	NPC130756
0.89	High Similarity	NPC12931
0.89	High Similarity	NPC70677
0.8889	High Similarity	NPC475078
0.8889	High Similarity	NPC6597
0.8889	High Similarity	NPC79241
0.8835	High Similarity	NPC155072
0.8835	High Similarity	NPC53740
0.8835	High Similarity	NPC67250
0.8824	High Similarity	NPC475225
0.8812	High Similarity	NPC477685
0.8774	High Similarity	NPC266937
0.8774	High Similarity	NPC77772
0.8774	High Similarity	NPC470770
0.8774	High Similarity	NPC469912
0.8725	High Similarity	NPC235762
0.8725	High Similarity	NPC471228
0.8713	High Similarity	NPC174911
0.8713	High Similarity	NPC130103
0.87	High Similarity	NPC156313
0.8692	High Similarity	NPC177962
0.8692	High Similarity	NPC302371
0.8692	High Similarity	NPC62867
0.8673	High Similarity	NPC55903
0.8654	High Similarity	NPC54765
0.8654	High Similarity	NPC469913
0.8646	High Similarity	NPC27974
0.8627	High Similarity	NPC80800
0.8614	High Similarity	NPC299762
0.8614	High Similarity	NPC33675
0.8598	High Similarity	NPC54373
0.8586	High Similarity	NPC152415
0.8571	High Similarity	NPC66834
0.8571	High Similarity	NPC304541
0.8571	High Similarity	NPC306074
0.8571	High Similarity	NPC231150
0.8558	High Similarity	NPC471350
0.8558	High Similarity	NPC117115
0.8544	High Similarity	NPC168393
0.8542	High Similarity	NPC307235
0.8542	High Similarity	NPC407
0.8532	High Similarity	NPC471534
0.8515	High Similarity	NPC77492
0.8515	High Similarity	NPC474073
0.8515	High Similarity	NPC88420
0.8505	High Similarity	NPC132720
0.85	High Similarity	NPC8392
0.8491	Intermediate Similarity	NPC95344
0.8485	Intermediate Similarity	NPC3358
0.8485	Intermediate Similarity	NPC147284
0.8485	Intermediate Similarity	NPC210497
0.8485	Intermediate Similarity	NPC162314
0.8485	Intermediate Similarity	NPC94139
0.8485	Intermediate Similarity	NPC306884
0.8476	Intermediate Similarity	NPC21594
0.8469	Intermediate Similarity	NPC192
0.8462	Intermediate Similarity	NPC130817
0.8462	Intermediate Similarity	NPC238696
0.8447	Intermediate Similarity	NPC252105
0.8438	Intermediate Similarity	NPC155393
0.8426	Intermediate Similarity	NPC275627
0.8416	Intermediate Similarity	NPC202986
0.8411	Intermediate Similarity	NPC473524
0.8411	Intermediate Similarity	NPC58865
0.8396	Intermediate Similarity	NPC233320
0.8396	Intermediate Similarity	NPC151477
0.8378	Intermediate Similarity	NPC141001
0.8367	Intermediate Similarity	NPC258219
0.835	Intermediate Similarity	NPC211885
0.8333	Intermediate Similarity	NPC13482
0.8333	Intermediate Similarity	NPC32674
0.8333	Intermediate Similarity	NPC286904
0.8333	Intermediate Similarity	NPC150837
0.8318	Intermediate Similarity	NPC68260
0.8318	Intermediate Similarity	NPC64586
0.8318	Intermediate Similarity	NPC11554
0.8318	Intermediate Similarity	NPC279887
0.8317	Intermediate Similarity	NPC222146
0.8317	Intermediate Similarity	NPC274678
0.8302	Intermediate Similarity	NPC310456
0.83	Intermediate Similarity	NPC271440
0.8286	Intermediate Similarity	NPC323810
0.8286	Intermediate Similarity	NPC93831
0.8283	Intermediate Similarity	NPC312304
0.8265	Intermediate Similarity	NPC19680
0.8257	Intermediate Similarity	NPC151537
0.8257	Intermediate Similarity	NPC95716
0.8252	Intermediate Similarity	NPC122005
0.8252	Intermediate Similarity	NPC252821
0.8241	Intermediate Similarity	NPC282855
0.8241	Intermediate Similarity	NPC26013
0.8241	Intermediate Similarity	NPC98392
0.8224	Intermediate Similarity	NPC474352
0.8218	Intermediate Similarity	NPC128062
0.8218	Intermediate Similarity	NPC76938
0.8218	Intermediate Similarity	NPC289769
0.8218	Intermediate Similarity	NPC27323
0.8218	Intermediate Similarity	NPC316301
0.8208	Intermediate Similarity	NPC138942
0.82	Intermediate Similarity	NPC204210
0.82	Intermediate Similarity	NPC155908
0.8182	Intermediate Similarity	NPC228452
0.8182	Intermediate Similarity	NPC46940
0.8182	Intermediate Similarity	NPC98372
0.8182	Intermediate Similarity	NPC123273
0.8182	Intermediate Similarity	NPC318325
0.8182	Intermediate Similarity	NPC250323
0.8182	Intermediate Similarity	NPC242240
0.8182	Intermediate Similarity	NPC473521
0.8173	Intermediate Similarity	NPC225506
0.8165	Intermediate Similarity	NPC141782
0.8165	Intermediate Similarity	NPC224870
0.8165	Intermediate Similarity	NPC208229
0.8163	Intermediate Similarity	NPC23167
0.8158	Intermediate Similarity	NPC323074
0.8148	Intermediate Similarity	NPC306295
0.8148	Intermediate Similarity	NPC233835
0.8137	Intermediate Similarity	NPC32714
0.8113	Intermediate Similarity	NPC327811
0.8113	Intermediate Similarity	NPC227458
0.8113	Intermediate Similarity	NPC244513
0.8113	Intermediate Similarity	NPC120719
0.8113	Intermediate Similarity	NPC254965
0.8113	Intermediate Similarity	NPC288411
0.8113	Intermediate Similarity	NPC102216
0.8113	Intermediate Similarity	NPC218879
0.8108	Intermediate Similarity	NPC715
0.8091	Intermediate Similarity	NPC224527
0.8091	Intermediate Similarity	NPC260323
0.8091	Intermediate Similarity	NPC176279
0.8091	Intermediate Similarity	NPC228609
0.8087	Intermediate Similarity	NPC318581
0.8087	Intermediate Similarity	NPC477037
0.8087	Intermediate Similarity	NPC325544
0.8081	Intermediate Similarity	NPC25493
0.8081	Intermediate Similarity	NPC113460
0.8077	Intermediate Similarity	NPC92730
0.8077	Intermediate Similarity	NPC128723
0.8073	Intermediate Similarity	NPC202647
0.8073	Intermediate Similarity	NPC314187
0.8073	Intermediate Similarity	NPC186385
0.8073	Intermediate Similarity	NPC299568
0.8061	Intermediate Similarity	NPC197783
0.8058	Intermediate Similarity	NPC216520
0.8058	Intermediate Similarity	NPC82664
0.8058	Intermediate Similarity	NPC473388
0.8058	Intermediate Similarity	NPC132271
0.8058	Intermediate Similarity	NPC292730
0.8056	Intermediate Similarity	NPC204901
0.8056	Intermediate Similarity	NPC232523
0.8056	Intermediate Similarity	NPC158253
0.8053	Intermediate Similarity	NPC469663
0.8053	Intermediate Similarity	NPC92
0.8053	Intermediate Similarity	NPC308828
0.8037	Intermediate Similarity	NPC239291
0.8037	Intermediate Similarity	NPC37802
0.8036	Intermediate Similarity	NPC268160
0.8036	Intermediate Similarity	NPC107240
0.8036	Intermediate Similarity	NPC470837
0.8036	Intermediate Similarity	NPC195922
0.8036	Intermediate Similarity	NPC249270
0.802	Intermediate Similarity	NPC45040
0.8019	Intermediate Similarity	NPC71002
0.8019	Intermediate Similarity	NPC242342
0.8019	Intermediate Similarity	NPC53051
0.8019	Intermediate Similarity	NPC302219
0.8019	Intermediate Similarity	NPC106396
0.8019	Intermediate Similarity	NPC168829
0.8019	Intermediate Similarity	NPC94351
0.8019	Intermediate Similarity	NPC168303
0.8019	Intermediate Similarity	NPC146798
0.8019	Intermediate Similarity	NPC222522
0.8019	Intermediate Similarity	NPC249828
0.8019	Intermediate Similarity	NPC85479
0.8019	Intermediate Similarity	NPC24404
0.8019	Intermediate Similarity	NPC313030
0.8018	Intermediate Similarity	NPC228425
0.8018	Intermediate Similarity	NPC26615
0.8018	Intermediate Similarity	NPC471179
0.8017	Intermediate Similarity	NPC100108
0.8017	Intermediate Similarity	NPC129176
0.8017	Intermediate Similarity	NPC277798
0.8	Intermediate Similarity	NPC471535

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 NPC475580 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	1078
0.2-0.3	1402
0.3-0.4	3009
0.4-0.5	1812
0.5-0.6	1115
0.6-0.7	376
0.7-0.8	58
0.8-0.85	12
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9286	High Similarity	NPD289	Clinical (unspecified phase)
0.898	High Similarity	NPD288	Approved
0.8692	High Similarity	NPD7635	Approved
0.8687	High Similarity	NPD844	Approved
0.8485	Intermediate Similarity	NPD845	Approved
0.8252	Intermediate Similarity	NPD3020	Approved
0.8218	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8073	Intermediate Similarity	NPD4750	Phase 3
0.8056	Intermediate Similarity	NPD2342	Discontinued
0.7965	Intermediate Similarity	NPD6671	Approved
0.7963	Intermediate Similarity	NPD1444	Approved
0.7963	Intermediate Similarity	NPD1445	Approved
0.7961	Intermediate Similarity	NPD2860	Approved
0.7961	Intermediate Similarity	NPD1809	Phase 2
0.7961	Intermediate Similarity	NPD2859	Approved
0.7925	Intermediate Similarity	NPD940	Approved
0.7925	Intermediate Similarity	NPD846	Approved
0.7909	Intermediate Similarity	NPD1792	Phase 2
0.7909	Intermediate Similarity	NPD3021	Approved
0.7909	Intermediate Similarity	NPD3022	Approved
0.7876	Intermediate Similarity	NPD497	Approved
0.7864	Intermediate Similarity	NPD2933	Approved
0.7864	Intermediate Similarity	NPD2934	Approved
0.7857	Intermediate Similarity	NPD111	Approved
0.7788	Intermediate Similarity	NPD495	Approved
0.7788	Intermediate Similarity	NPD496	Approved
0.7788	Intermediate Similarity	NPD498	Approved
0.7607	Intermediate Similarity	NPD3091	Approved
0.7521	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9088	Approved
0.75	Intermediate Similarity	NPD1242	Phase 1
0.7479	Intermediate Similarity	NPD2932	Approved
0.7479	Intermediate Similarity	NPD3019	Approved
0.7479	Intermediate Similarity	NPD4059	Approved
0.7478	Intermediate Similarity	NPD1398	Phase 1
0.7459	Intermediate Similarity	NPD6696	Suspended
0.7458	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7340	Approved
0.7436	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD4093	Discontinued
0.7364	Intermediate Similarity	NPD9500	Approved
0.7355	Intermediate Similarity	NPD3092	Approved
0.7355	Intermediate Similarity	NPD1201	Approved
0.735	Intermediate Similarity	NPD709	Approved
0.7333	Intermediate Similarity	NPD4626	Approved
0.7333	Intermediate Similarity	NPD1751	Approved
0.7328	Intermediate Similarity	NPD2228	Approved
0.7328	Intermediate Similarity	NPD2229	Approved
0.7328	Intermediate Similarity	NPD2234	Approved
0.7321	Intermediate Similarity	NPD968	Approved
0.7315	Intermediate Similarity	NPD9273	Approved
0.7304	Intermediate Similarity	NPD228	Approved
0.7295	Intermediate Similarity	NPD2230	Approved
0.7295	Intermediate Similarity	NPD2233	Approved
0.7295	Intermediate Similarity	NPD2232	Approved
0.7288	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD2861	Phase 2
0.7265	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD9614	Approved
0.7265	Intermediate Similarity	NPD9618	Approved
0.7265	Intermediate Similarity	NPD1791	Approved
0.7265	Intermediate Similarity	NPD1793	Approved
0.7258	Intermediate Similarity	NPD3094	Phase 2
0.7213	Intermediate Similarity	NPD1611	Approved
0.72	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3095	Discontinued
0.719	Intermediate Similarity	NPD2286	Discontinued
0.7155	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9608	Approved
0.7143	Intermediate Similarity	NPD9610	Approved
0.7131	Intermediate Similarity	NPD3496	Discontinued
0.712	Intermediate Similarity	NPD1470	Approved
0.7097	Intermediate Similarity	NPD4749	Approved
0.7094	Intermediate Similarity	NPD9379	Approved
0.7094	Intermediate Similarity	NPD9377	Approved
0.7083	Intermediate Similarity	NPD9616	Approved
0.7083	Intermediate Similarity	NPD9615	Approved
0.7083	Intermediate Similarity	NPD9613	Approved
0.7083	Intermediate Similarity	NPD9087	Approved
0.7073	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD9295	Approved
0.7034	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD4625	Phase 3
0.7025	Intermediate Similarity	NPD5303	Approved
0.7025	Intermediate Similarity	NPD316	Approved
0.7025	Intermediate Similarity	NPD5304	Approved
0.7008	Intermediate Similarity	NPD5736	Approved
0.7008	Intermediate Similarity	NPD1712	Approved
0.7	Intermediate Similarity	NPD4060	Phase 1
0.6984	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD475	Phase 2
0.6967	Remote Similarity	NPD5691	Approved
0.6957	Remote Similarity	NPD290	Approved
0.6935	Remote Similarity	NPD1610	Phase 2
0.6929	Remote Similarity	NPD2194	Approved
0.6929	Remote Similarity	NPD2195	Approved
0.6923	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD4589	Approved
0.6905	Remote Similarity	NPD1283	Approved
0.6903	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5283	Phase 1
0.6875	Remote Similarity	NPD3637	Approved
0.6875	Remote Similarity	NPD3636	Approved
0.6875	Remote Similarity	NPD3028	Approved
0.6875	Remote Similarity	NPD3635	Approved
0.6869	Remote Similarity	NPD9294	Approved
0.6855	Remote Similarity	NPD3023	Approved
0.6855	Remote Similarity	NPD3026	Approved
0.6838	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3025	Approved
0.6829	Remote Similarity	NPD3024	Approved
0.6825	Remote Similarity	NPD1755	Approved
0.6822	Remote Similarity	NPD600	Approved
0.6822	Remote Similarity	NPD2605	Approved
0.6822	Remote Similarity	NPD596	Approved
0.6822	Remote Similarity	NPD2606	Approved
0.6807	Remote Similarity	NPD1138	Approved
0.6797	Remote Similarity	NPD4624	Approved
0.6794	Remote Similarity	NPD6663	Approved
0.6777	Remote Similarity	NPD256	Approved
0.6777	Remote Similarity	NPD255	Approved
0.6774	Remote Similarity	NPD9381	Approved
0.6774	Remote Similarity	NPD9384	Approved
0.6769	Remote Similarity	NPD5156	Approved
0.6769	Remote Similarity	NPD5155	Approved
0.6767	Remote Similarity	NPD4097	Suspended
0.6752	Remote Similarity	NPD74	Approved
0.6752	Remote Similarity	NPD9266	Approved
0.6752	Remote Similarity	NPD2684	Approved
0.6748	Remote Similarity	NPD7330	Discontinued
0.6746	Remote Similarity	NPD1608	Approved
0.6742	Remote Similarity	NPD2238	Phase 2
0.6723	Remote Similarity	NPD1137	Approved
0.6723	Remote Similarity	NPD1139	Approved
0.6721	Remote Similarity	NPD9493	Approved
0.6718	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD9089	Approved
0.6694	Remote Similarity	NPD1651	Approved
0.6694	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD1669	Approved
0.6693	Remote Similarity	NPD9622	Approved
0.6692	Remote Similarity	NPD3594	Approved
0.6692	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD4908	Phase 1
0.6692	Remote Similarity	NPD3595	Approved
0.6691	Remote Similarity	NPD4726	Approved
0.6691	Remote Similarity	NPD4725	Approved
0.6691	Remote Similarity	NPD4721	Approved
0.6667	Remote Similarity	NPD9267	Approved
0.6667	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9264	Approved
0.6667	Remote Similarity	NPD9263	Approved
0.6667	Remote Similarity	NPD839	Approved
0.6667	Remote Similarity	NPD840	Approved
0.6667	Remote Similarity	NPD1281	Approved
0.6667	Remote Similarity	NPD7644	Approved
0.6642	Remote Similarity	NPD4257	Approved
0.6642	Remote Similarity	NPD4256	Phase 2
0.6642	Remote Similarity	NPD2157	Approved
0.664	Remote Similarity	NPD2668	Approved
0.664	Remote Similarity	NPD1778	Approved
0.664	Remote Similarity	NPD2667	Approved
0.664	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7157	Approved
0.6618	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD2935	Discontinued
0.6617	Remote Similarity	NPD3620	Phase 2
0.6617	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD2237	Approved
0.6614	Remote Similarity	NPD2235	Phase 2
0.6614	Remote Similarity	NPD2231	Phase 2
0.6613	Remote Similarity	NPD1548	Phase 1
0.6613	Remote Similarity	NPD1759	Phase 1
0.6602	Remote Similarity	NPD9093	Approved
0.6591	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD2797	Approved
0.6589	Remote Similarity	NPD1164	Approved
0.6587	Remote Similarity	NPD1980	Approved
0.6587	Remote Similarity	NPD1981	Approved
0.6587	Remote Similarity	NPD1983	Approved
0.6587	Remote Similarity	NPD3143	Discontinued
0.6585	Remote Similarity	NPD7636	Approved
0.6579	Remote Similarity	NPD1616	Discontinued
0.6571	Remote Similarity	NPD3300	Phase 2
0.6569	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5327	Phase 3
0.656	Remote Similarity	NPD3444	Approved
0.656	Remote Similarity	NPD3443	Approved
0.656	Remote Similarity	NPD3445	Approved
0.6552	Remote Similarity	NPD9244	Approved
0.6549	Remote Similarity	NPD6090	Discontinued
0.6544	Remote Similarity	NPD7743	Approved
0.6544	Remote Similarity	NPD7742	Approved
0.6544	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD1753	Discontinued
0.6544	Remote Similarity	NPD651	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