NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.09
Volume:	288.118
LogP:	3.457
LogD:	3.66
LogS:	-3.574
# Rotatable Bonds:	3
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.839
Synthetic Accessibility Score:	2.389
Fsp3:	0.059
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.56
MDCK Permeability:	1.3144307558832224e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.872
30% Bioavailability (F30%):	0.709

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	98.16082000732422%
Volume Distribution (VD):	0.445
Pgp-substrate:	0.7587635517120361%

ADMET: Metabolism

CYP1A2-inhibitor:	0.963
CYP1A2-substrate:	0.136
CYP2C19-inhibitor:	0.96
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.867
CYP2C9-substrate:	0.987
CYP2D6-inhibitor:	0.892
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.909
CYP3A4-substrate:	0.439

ADMET: Excretion

Clearance (CL):	13.053
Half-life (T1/2):	0.787

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.274
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.745
Rat Oral Acute Toxicity:	0.127
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.946
Carcinogencity:	0.837
Eye Corrosion:	0.575
Eye Irritation:	0.988
Respiratory Toxicity:	0.796

Download Data

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

Natural Product: NPC266932

Natural Product ID:	NPC266932
*Common Name:**	Asparenydiol
IUPAC Name:	4-[(E)-5-(4-hydroxyphenoxy)pent-3-en-1-ynyl]phenol
Synonyms:	Asparenydiol
Standard InCHIKey:	GXRXAVMCQJHRCM-HNQUOIGGSA-N
Standard InCHI:	InChI=1S/C17H14O3/c18-15-7-5-14(6-8-15)4-2-1-3-13-20-17-11-9-16(19)10-12-17/h1,3,5-12,18-19H,13H2/b3-1+
SMILES:	C(=CCOc1ccc(cc1)O)/C#Cc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452743
PubChem CID:	10084256
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004628] 4-alkoxyphenols

*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
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14987058]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5
Others	1

Activity Type	# Activity
Cell Line	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	8500.0	nM	PMID[545532]
NPT1851	Cell Line	Col2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[545532]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[545532]
NPT1034	Cell Line	Lu1	Homo sapiens	IC50	=	70100.0	nM	PMID[545532]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[545532]
NPT27	Others	Unspecified		CC50	<	18000.0	nM	PMID[545532]

☑ 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 NPC266932 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	328
0.1-0.2	2277
0.2-0.3	8241
0.3-0.4	11415
0.4-0.5	4047
0.5-0.6	8178
0.6-0.7	6668
0.7-0.8	1471
0.8-0.85	61
0.85-0.9	10
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8803	High Similarity	NPC74478
0.8679	High Similarity	NPC192596
0.8611	High Similarity	NPC113457
0.8598	High Similarity	NPC12987
0.8598	High Similarity	NPC474603
0.8585	High Similarity	NPC51633
0.8584	High Similarity	NPC301321
0.8519	High Similarity	NPC470393
0.8519	High Similarity	NPC8302
0.8455	Intermediate Similarity	NPC201959
0.8426	Intermediate Similarity	NPC38079
0.8426	Intermediate Similarity	NPC108875
0.8407	Intermediate Similarity	NPC301735
0.8319	Intermediate Similarity	NPC474920
0.8291	Intermediate Similarity	NPC163036
0.8291	Intermediate Similarity	NPC295259
0.8288	Intermediate Similarity	NPC75440
0.8224	Intermediate Similarity	NPC471576
0.8224	Intermediate Similarity	NPC100870
0.8214	Intermediate Similarity	NPC474272
0.8205	Intermediate Similarity	NPC74821
0.819	Intermediate Similarity	NPC290470
0.819	Intermediate Similarity	NPC154256
0.8165	Intermediate Similarity	NPC305205
0.8158	Intermediate Similarity	NPC115379
0.8151	Intermediate Similarity	NPC318357
0.8142	Intermediate Similarity	NPC46844
0.8125	Intermediate Similarity	NPC169450
0.8125	Intermediate Similarity	NPC206341
0.812	Intermediate Similarity	NPC86947
0.8108	Intermediate Similarity	NPC135464
0.8108	Intermediate Similarity	NPC92623
0.8103	Intermediate Similarity	NPC473718
0.8103	Intermediate Similarity	NPC296526
0.8087	Intermediate Similarity	NPC35344
0.8087	Intermediate Similarity	NPC141003
0.8083	Intermediate Similarity	NPC54972
0.8083	Intermediate Similarity	NPC290451
0.8083	Intermediate Similarity	NPC127389
0.807	Intermediate Similarity	NPC296920
0.807	Intermediate Similarity	NPC90520
0.8067	Intermediate Similarity	NPC8283
0.8067	Intermediate Similarity	NPC258979
0.8067	Intermediate Similarity	NPC93398
0.8053	Intermediate Similarity	NPC306045
0.8053	Intermediate Similarity	NPC265211
0.8036	Intermediate Similarity	NPC260952
0.8036	Intermediate Similarity	NPC233320
0.8018	Intermediate Similarity	NPC154899
0.8018	Intermediate Similarity	NPC233396
0.8017	Intermediate Similarity	NPC100099
0.8017	Intermediate Similarity	NPC180508
0.8017	Intermediate Similarity	NPC228287
0.8017	Intermediate Similarity	NPC150026
0.8017	Intermediate Similarity	NPC161696
0.8017	Intermediate Similarity	NPC36016
0.8	Intermediate Similarity	NPC280606
0.8	Intermediate Similarity	NPC129176
0.8	Intermediate Similarity	NPC165646
0.7983	Intermediate Similarity	NPC256369
0.7983	Intermediate Similarity	NPC32152
0.7981	Intermediate Similarity	NPC259134
0.7981	Intermediate Similarity	NPC99886
0.7981	Intermediate Similarity	NPC8002
0.7981	Intermediate Similarity	NPC177844
0.7967	Intermediate Similarity	NPC28476
0.7967	Intermediate Similarity	NPC81641
0.7967	Intermediate Similarity	NPC133407
0.7965	Intermediate Similarity	NPC241549
0.7951	Intermediate Similarity	NPC38761
0.7951	Intermediate Similarity	NPC76465
0.7949	Intermediate Similarity	NPC464
0.7949	Intermediate Similarity	NPC185541
0.7949	Intermediate Similarity	NPC51345
0.7946	Intermediate Similarity	NPC326801
0.7934	Intermediate Similarity	NPC476165
0.7934	Intermediate Similarity	NPC193364
0.7928	Intermediate Similarity	NPC283546
0.7917	Intermediate Similarity	NPC232295
0.7917	Intermediate Similarity	NPC474131
0.7917	Intermediate Similarity	NPC263835
0.7913	Intermediate Similarity	NPC55300
0.7913	Intermediate Similarity	NPC255068
0.7909	Intermediate Similarity	NPC300166
0.7905	Intermediate Similarity	NPC71853
0.7903	Intermediate Similarity	NPC230479
0.7903	Intermediate Similarity	NPC50315
0.7903	Intermediate Similarity	NPC58607
0.7903	Intermediate Similarity	NPC191037
0.7903	Intermediate Similarity	NPC26879
0.7903	Intermediate Similarity	NPC178284
0.7903	Intermediate Similarity	NPC283049
0.7899	Intermediate Similarity	NPC283616
0.789	Intermediate Similarity	NPC216468
0.789	Intermediate Similarity	NPC51333
0.789	Intermediate Similarity	NPC171843
0.789	Intermediate Similarity	NPC78119
0.789	Intermediate Similarity	NPC132078
0.7886	Intermediate Similarity	NPC94276
0.7886	Intermediate Similarity	NPC109822
0.7886	Intermediate Similarity	NPC106914
0.7886	Intermediate Similarity	NPC86502
0.7886	Intermediate Similarity	NPC293701
0.7886	Intermediate Similarity	NPC134195
0.7886	Intermediate Similarity	NPC197351
0.7886	Intermediate Similarity	NPC48990
0.7886	Intermediate Similarity	NPC114901
0.7886	Intermediate Similarity	NPC246648
0.7885	Intermediate Similarity	NPC104216
0.7885	Intermediate Similarity	NPC157213
0.7881	Intermediate Similarity	NPC85292
0.7881	Intermediate Similarity	NPC69539
0.7881	Intermediate Similarity	NPC54507
0.7881	Intermediate Similarity	NPC229147
0.7881	Intermediate Similarity	NPC19290
0.7876	Intermediate Similarity	NPC194034
0.7876	Intermediate Similarity	NPC251306
0.7876	Intermediate Similarity	NPC151530
0.7876	Intermediate Similarity	NPC157473
0.7863	Intermediate Similarity	NPC235250
0.7857	Intermediate Similarity	NPC128730
0.7857	Intermediate Similarity	NPC473855
0.7851	Intermediate Similarity	NPC473875
0.785	Intermediate Similarity	NPC471581
0.785	Intermediate Similarity	NPC151715
0.7845	Intermediate Similarity	NPC290353
0.7845	Intermediate Similarity	NPC42911
0.7845	Intermediate Similarity	NPC153795
0.784	Intermediate Similarity	NPC163332
0.784	Intermediate Similarity	NPC183181
0.784	Intermediate Similarity	NPC319625
0.784	Intermediate Similarity	NPC292056
0.784	Intermediate Similarity	NPC111247
0.784	Intermediate Similarity	NPC118787
0.784	Intermediate Similarity	NPC147821
0.784	Intermediate Similarity	NPC41706
0.7833	Intermediate Similarity	NPC471449
0.7833	Intermediate Similarity	NPC51341
0.783	Intermediate Similarity	NPC321956
0.783	Intermediate Similarity	NPC45040
0.7826	Intermediate Similarity	NPC183700
0.7826	Intermediate Similarity	NPC94045
0.7823	Intermediate Similarity	NPC103420
0.7823	Intermediate Similarity	NPC167571
0.7823	Intermediate Similarity	NPC17809
0.7823	Intermediate Similarity	NPC188022
0.7823	Intermediate Similarity	NPC285040
0.7823	Intermediate Similarity	NPC278552
0.7823	Intermediate Similarity	NPC102540
0.7823	Intermediate Similarity	NPC194519
0.7823	Intermediate Similarity	NPC87113
0.7823	Intermediate Similarity	NPC207179
0.7818	Intermediate Similarity	NPC213730
0.7818	Intermediate Similarity	NPC107101
0.7815	Intermediate Similarity	NPC238176
0.7815	Intermediate Similarity	NPC187993
0.7815	Intermediate Similarity	NPC474933
0.7805	Intermediate Similarity	NPC261992
0.7798	Intermediate Similarity	NPC95755
0.7788	Intermediate Similarity	NPC176971
0.7787	Intermediate Similarity	NPC97432
0.7787	Intermediate Similarity	NPC190454
0.7778	Intermediate Similarity	NPC47283
0.7778	Intermediate Similarity	NPC176730
0.7778	Intermediate Similarity	NPC38664
0.7778	Intermediate Similarity	NPC39064
0.7778	Intermediate Similarity	NPC72529
0.7778	Intermediate Similarity	NPC274717
0.7778	Intermediate Similarity	NPC26244
0.7778	Intermediate Similarity	NPC123175
0.7778	Intermediate Similarity	NPC87224
0.7778	Intermediate Similarity	NPC222572
0.7778	Intermediate Similarity	NPC53986
0.7768	Intermediate Similarity	NPC130817
0.7768	Intermediate Similarity	NPC2518
0.776	Intermediate Similarity	NPC276212
0.776	Intermediate Similarity	NPC471215
0.776	Intermediate Similarity	NPC262573
0.7759	Intermediate Similarity	NPC78918
0.7759	Intermediate Similarity	NPC139617
0.7759	Intermediate Similarity	NPC275627
0.775	Intermediate Similarity	NPC101503
0.775	Intermediate Similarity	NPC470626
0.775	Intermediate Similarity	NPC131118
0.7748	Intermediate Similarity	NPC7686
0.7748	Intermediate Similarity	NPC40258
0.7748	Intermediate Similarity	NPC91461
0.7748	Intermediate Similarity	NPC307425
0.7742	Intermediate Similarity	NPC270030
0.7742	Intermediate Similarity	NPC61685
0.7739	Intermediate Similarity	NPC36108
0.7739	Intermediate Similarity	NPC7097
0.7739	Intermediate Similarity	NPC233731
0.7739	Intermediate Similarity	NPC79543
0.7739	Intermediate Similarity	NPC246358
0.7736	Intermediate Similarity	NPC300017
0.7731	Intermediate Similarity	NPC473556
0.7731	Intermediate Similarity	NPC141090
0.7731	Intermediate Similarity	NPC163398
0.7731	Intermediate Similarity	NPC203113

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 NPC266932 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	1119
0.2-0.3	1657
0.3-0.4	2677
0.4-0.5	1703
0.5-0.6	1074
0.6-0.7	523
0.7-0.8	89
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9327	High Similarity	NPD968	Approved
0.8205	Intermediate Similarity	NPD1548	Phase 1
0.813	Intermediate Similarity	NPD2861	Phase 2
0.8125	Intermediate Similarity	NPD2684	Approved
0.8103	Intermediate Similarity	NPD6671	Approved
0.8083	Intermediate Similarity	NPD1535	Discovery
0.8017	Intermediate Similarity	NPD1481	Phase 2
0.7951	Intermediate Similarity	NPD6583	Phase 3
0.7951	Intermediate Similarity	NPD6582	Phase 2
0.7934	Intermediate Similarity	NPD1610	Phase 2
0.7899	Intermediate Similarity	NPD1894	Discontinued
0.7885	Intermediate Similarity	NPD9295	Approved
0.7876	Intermediate Similarity	NPD290	Approved
0.785	Intermediate Similarity	NPD2934	Approved
0.785	Intermediate Similarity	NPD2933	Approved
0.7845	Intermediate Similarity	NPD7843	Approved
0.7845	Intermediate Similarity	NPD821	Approved
0.7778	Intermediate Similarity	NPD2860	Approved
0.7778	Intermediate Similarity	NPD2859	Approved
0.7769	Intermediate Similarity	NPD6516	Phase 2
0.7769	Intermediate Similarity	NPD5846	Approved
0.776	Intermediate Similarity	NPD6584	Phase 3
0.775	Intermediate Similarity	NPD1182	Approved
0.7692	Intermediate Similarity	NPD5535	Approved
0.7686	Intermediate Similarity	NPD6382	Discontinued
0.7647	Intermediate Similarity	NPD7157	Approved
0.7638	Intermediate Similarity	NPD4908	Phase 1
0.7632	Intermediate Similarity	NPD3134	Approved
0.7607	Intermediate Similarity	NPD228	Approved
0.7597	Intermediate Similarity	NPD6233	Phase 2
0.7586	Intermediate Similarity	NPD5451	Approved
0.7583	Intermediate Similarity	NPD3596	Phase 2
0.7581	Intermediate Similarity	NPD2235	Phase 2
0.7581	Intermediate Similarity	NPD2231	Phase 2
0.757	Intermediate Similarity	NPD9365	Approved
0.7568	Intermediate Similarity	NPD3020	Approved
0.7561	Intermediate Similarity	NPD3496	Discontinued
0.7519	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD111	Approved
0.7479	Intermediate Similarity	NPD1241	Discontinued
0.7459	Intermediate Similarity	NPD6580	Approved
0.7459	Intermediate Similarity	NPD6581	Approved
0.744	Intermediate Similarity	NPD1840	Phase 2
0.7422	Intermediate Similarity	NPD4993	Discontinued
0.7414	Intermediate Similarity	NPD1358	Approved
0.7405	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1613	Approved
0.7405	Intermediate Similarity	NPD4060	Phase 1
0.7398	Intermediate Similarity	NPD5585	Approved
0.7398	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD422	Phase 1
0.736	Intermediate Similarity	NPD1091	Approved
0.7355	Intermediate Similarity	NPD2557	Approved
0.7345	Intermediate Similarity	NPD1242	Phase 1
0.7333	Intermediate Similarity	NPD5283	Phase 1
0.7308	Intermediate Similarity	NPD5163	Phase 2
0.7308	Intermediate Similarity	NPD3027	Phase 3
0.7293	Intermediate Similarity	NPD6353	Approved
0.7293	Intermediate Similarity	NPD3052	Approved
0.7293	Intermediate Similarity	NPD3054	Approved
0.7287	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD3847	Discontinued
0.7266	Intermediate Similarity	NPD4098	Discontinued
0.7252	Intermediate Similarity	NPD6798	Discontinued
0.7252	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4129	Approved
0.7244	Intermediate Similarity	NPD3685	Discontinued
0.7241	Intermediate Similarity	NPD9697	Approved
0.7209	Intermediate Similarity	NPD4624	Approved
0.72	Intermediate Similarity	NPD2668	Approved
0.72	Intermediate Similarity	NPD2667	Approved
0.7197	Intermediate Similarity	NPD4062	Phase 3
0.7188	Intermediate Similarity	NPD3225	Approved
0.7176	Intermediate Similarity	NPD6179	Discontinued
0.7143	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1203	Approved
0.7132	Intermediate Similarity	NPD2797	Approved
0.7132	Intermediate Similarity	NPD1537	Approved
0.7132	Intermediate Similarity	NPD3568	Approved
0.7132	Intermediate Similarity	NPD1538	Phase 1
0.7132	Intermediate Similarity	NPD1519	Approved
0.7132	Intermediate Similarity	NPD3567	Approved
0.713	Intermediate Similarity	NPD291	Approved
0.7121	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD3049	Approved
0.712	Intermediate Similarity	NPD2595	Approved
0.712	Intermediate Similarity	NPD1357	Approved
0.712	Intermediate Similarity	NPD3443	Approved
0.712	Intermediate Similarity	NPD3444	Approved
0.712	Intermediate Similarity	NPD2594	Approved
0.712	Intermediate Similarity	NPD3445	Approved
0.7111	Intermediate Similarity	NPD4538	Approved
0.7111	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4536	Approved
0.7109	Intermediate Similarity	NPD5327	Phase 3
0.7109	Intermediate Similarity	NPD6539	Approved
0.7109	Intermediate Similarity	NPD2429	Approved
0.7109	Intermediate Similarity	NPD4359	Approved
0.7109	Intermediate Similarity	NPD6540	Phase 3
0.7109	Intermediate Similarity	NPD2428	Approved
0.7109	Intermediate Similarity	NPD6542	Approved
0.7109	Intermediate Similarity	NPD6543	Approved
0.7097	Intermediate Similarity	NPD5536	Phase 2
0.709	Intermediate Similarity	NPD4340	Discontinued
0.709	Intermediate Similarity	NPD6355	Discontinued
0.7087	Intermediate Similarity	NPD1611	Approved
0.7077	Intermediate Similarity	NPD3691	Phase 2
0.7077	Intermediate Similarity	NPD3690	Phase 2
0.7068	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7477	Discontinued
0.7063	Intermediate Similarity	NPD1778	Approved
0.7063	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2554	Approved
0.7063	Intermediate Similarity	NPD2556	Approved
0.7059	Intermediate Similarity	NPD5960	Phase 3
0.7059	Intermediate Similarity	NPD5588	Approved
0.7054	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6696	Suspended
0.7054	Intermediate Similarity	NPD9296	Approved
0.7054	Intermediate Similarity	NPD6541	Approved
0.7054	Intermediate Similarity	NPD6538	Approved
0.7049	Intermediate Similarity	NPD1398	Phase 1
0.7045	Intermediate Similarity	NPD7095	Approved
0.7045	Intermediate Similarity	NPD4625	Phase 3
0.7043	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD2230	Approved
0.7031	Intermediate Similarity	NPD2233	Approved
0.7031	Intermediate Similarity	NPD2232	Approved
0.7031	Intermediate Similarity	NPD1608	Approved
0.7029	Intermediate Similarity	NPD7037	Approved
0.7016	Intermediate Similarity	NPD7340	Approved
0.7015	Intermediate Similarity	NPD1558	Phase 1
0.7015	Intermediate Similarity	NPD4140	Approved
0.7008	Intermediate Similarity	NPD3294	Phase 2
0.7007	Intermediate Similarity	NPD1523	Approved
0.7007	Intermediate Similarity	NPD2935	Discontinued
0.7007	Intermediate Similarity	NPD1522	Approved
0.7	Intermediate Similarity	NPD3021	Approved
0.7	Intermediate Similarity	NPD1232	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3827	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3022	Approved
0.699	Remote Similarity	NPD9088	Approved
0.6985	Remote Similarity	NPD7097	Phase 1
0.6985	Remote Similarity	NPD1536	Approved
0.6977	Remote Similarity	NPD4749	Approved
0.697	Remote Similarity	NPD682	Discontinued
0.697	Remote Similarity	NPD2614	Approved
0.697	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5735	Approved
0.6957	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7018	Phase 2
0.6942	Remote Similarity	NPD2673	Approved
0.6942	Remote Similarity	NPD2671	Approved
0.694	Remote Similarity	NPD7265	Discontinued
0.6935	Remote Similarity	NPD709	Approved
0.6934	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD4626	Approved
0.6929	Remote Similarity	NPD2107	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1283	Approved
0.6923	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8651	Approved
0.6906	Remote Similarity	NPD1549	Phase 2
0.6905	Remote Similarity	NPD2486	Discontinued
0.6905	Remote Similarity	NPD9545	Approved
0.6897	Remote Similarity	NPD3028	Approved
0.6894	Remote Similarity	NPD454	Approved
0.6884	Remote Similarity	NPD4476	Approved
0.6884	Remote Similarity	NPD4477	Approved
0.687	Remote Similarity	NPD1818	Approved
0.687	Remote Similarity	NPD1820	Approved
0.687	Remote Similarity	NPD1819	Approved
0.687	Remote Similarity	NPD1817	Approved
0.6866	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7294	Phase 1
0.6866	Remote Similarity	NPD3268	Approved
0.6866	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD9501	Approved
0.6861	Remote Similarity	NPD1521	Approved
0.6861	Remote Similarity	NPD1520	Approved
0.6857	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.685	Remote Similarity	NPD5691	Approved
0.685	Remote Similarity	NPD1651	Approved
0.6846	Remote Similarity	NPD2982	Phase 2
0.6846	Remote Similarity	NPD1669	Approved
0.6846	Remote Similarity	NPD2983	Phase 2
0.6846	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD846	Approved
0.6838	Remote Similarity	NPD940	Approved
0.6835	Remote Similarity	NPD2344	Approved
0.6833	Remote Similarity	NPD9552	Approved
0.6831	Remote Similarity	NPD7440	Discontinued
0.6829	Remote Similarity	NPD7635	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