NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.19
Volume:	295.197
LogP:	3.518
LogD:	3.33
LogS:	-3.251
# Rotatable Bonds:	7
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.793
Synthetic Accessibility Score:	3.149
Fsp3:	0.625
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:	-4.256
MDCK Permeability:	2.4093178581097163e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.333
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.416
Plasma Protein Binding (PPB):	86.0364761352539%
Volume Distribution (VD):	4.258
Pgp-substrate:	21.293725967407227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.458
CYP1A2-substrate:	0.702
CYP2C19-inhibitor:	0.319
CYP2C19-substrate:	0.892
CYP2C9-inhibitor:	0.458
CYP2C9-substrate:	0.692
CYP2D6-inhibitor:	0.378
CYP2D6-substrate:	0.245
CYP3A4-inhibitor:	0.668
CYP3A4-substrate:	0.618

ADMET: Excretion

Clearance (CL):	12.788
Half-life (T1/2):	0.705

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.1
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.138
Rat Oral Acute Toxicity:	0.107
Maximum Recommended Daily Dose:	0.052
Skin Sensitization:	0.889
Carcinogencity:	0.053
Eye Corrosion:	0.008
Eye Irritation:	0.55
Respiratory Toxicity:	0.083

Download Data

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

Natural Product: NPC228452

Natural Product ID:	NPC228452
*Common Name:**	(7S)-(+)-7-O-Methylsydonol
IUPAC Name:	5-(hydroxymethyl)-2-[(2S)-2-methoxy-6-methylheptan-2-yl]phenol
Synonyms:
Standard InCHIKey:	PWOXLPFACURSPD-INIZCTEOSA-N
Standard InCHI:	InChI=1S/C16H26O3/c1-12(2)6-5-9-16(3,19-4)14-8-7-13(11-17)10-15(14)18/h7-8,10,12,17-18H,5-6,9,11H2,1-4H3/t16-/m0/s1
SMILES:	CO[C@](c1ccc(cc1O)CO)(CCCC(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2397436
PubChem CID:	71713905
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
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18505285]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23647825]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24057165]

☑ 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
Others	2

Activity Type	# Activity
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	29.82	%	PMID[536285]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[536285]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	69.02	%	PMID[536285]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	13800.0	nM	PMID[536285]

☑ 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 NPC228452 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	269
0.1-0.2	1354
0.2-0.3	3739
0.3-0.4	11468
0.4-0.5	7889
0.5-0.6	8281
0.6-0.7	7353
0.7-0.8	2083
0.8-0.85	215
0.85-0.9	38
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9519	High Similarity	NPC66834
0.9231	High Similarity	NPC475225
0.9135	High Similarity	NPC471228
0.9135	High Similarity	NPC235762
0.8966	High Similarity	NPC261992
0.8947	High Similarity	NPC328485
0.8942	High Similarity	NPC72729
0.8942	High Similarity	NPC174911
0.8909	High Similarity	NPC302371
0.8879	High Similarity	NPC188997
0.8868	High Similarity	NPC130817
0.8839	High Similarity	NPC232165
0.875	High Similarity	NPC79241
0.875	High Similarity	NPC6597
0.8739	High Similarity	NPC26615
0.8727	High Similarity	NPC132720
0.8718	High Similarity	NPC325301
0.8704	High Similarity	NPC53740
0.8696	High Similarity	NPC160235
0.8696	High Similarity	NPC121866
0.8696	High Similarity	NPC151197
0.8684	High Similarity	NPC320864
0.8661	High Similarity	NPC190212
0.8661	High Similarity	NPC319803
0.8654	High Similarity	NPC312132
0.8654	High Similarity	NPC259512
0.8649	High Similarity	NPC54373
0.8624	High Similarity	NPC474352
0.8611	High Similarity	NPC47284
0.8571	High Similarity	NPC474073
0.8559	High Similarity	NPC18128
0.8559	High Similarity	NPC327070
0.8559	High Similarity	NPC77789
0.8545	High Similarity	NPC241549
0.8534	High Similarity	NPC38181
0.8534	High Similarity	NPC20230
0.8519	High Similarity	NPC323810
0.8505	High Similarity	NPC477685
0.8505	High Similarity	NPC80800
0.8505	High Similarity	NPC252105
0.85	High Similarity	NPC476254
0.85	High Similarity	NPC131397
0.8496	Intermediate Similarity	NPC261343
0.8491	Intermediate Similarity	NPC33675
0.8491	Intermediate Similarity	NPC299762
0.8482	Intermediate Similarity	NPC224527
0.8482	Intermediate Similarity	NPC275627
0.8468	Intermediate Similarity	NPC186385
0.8468	Intermediate Similarity	NPC299568
0.8455	Intermediate Similarity	NPC204901
0.8455	Intermediate Similarity	NPC233320
0.8455	Intermediate Similarity	NPC232523
0.8455	Intermediate Similarity	NPC158253
0.8448	Intermediate Similarity	NPC9592
0.8448	Intermediate Similarity	NPC48781
0.8448	Intermediate Similarity	NPC190514
0.8448	Intermediate Similarity	NPC283616
0.8443	Intermediate Similarity	NPC38604
0.8443	Intermediate Similarity	NPC211179
0.844	Intermediate Similarity	NPC471350
0.844	Intermediate Similarity	NPC37802
0.8426	Intermediate Similarity	NPC12870
0.8426	Intermediate Similarity	NPC24327
0.8426	Intermediate Similarity	NPC108497
0.8421	Intermediate Similarity	NPC470837
0.8421	Intermediate Similarity	NPC41851
0.8411	Intermediate Similarity	NPC129373
0.8411	Intermediate Similarity	NPC248396
0.8411	Intermediate Similarity	NPC48730
0.8396	Intermediate Similarity	NPC88420
0.8396	Intermediate Similarity	NPC152097
0.8396	Intermediate Similarity	NPC475078
0.839	Intermediate Similarity	NPC96423
0.8378	Intermediate Similarity	NPC169450
0.8376	Intermediate Similarity	NPC471449
0.8376	Intermediate Similarity	NPC51341
0.8376	Intermediate Similarity	NPC184302
0.8374	Intermediate Similarity	NPC472796
0.8374	Intermediate Similarity	NPC472795
0.8374	Intermediate Similarity	NPC472797
0.8364	Intermediate Similarity	NPC12640
0.8364	Intermediate Similarity	NPC30416
0.8364	Intermediate Similarity	NPC310456
0.8364	Intermediate Similarity	NPC201662
0.8364	Intermediate Similarity	NPC99836
0.8361	Intermediate Similarity	NPC66331
0.8349	Intermediate Similarity	NPC227458
0.8349	Intermediate Similarity	NPC218879
0.8349	Intermediate Similarity	NPC244513
0.8348	Intermediate Similarity	NPC474486
0.8347	Intermediate Similarity	NPC76119
0.8347	Intermediate Similarity	NPC33654
0.8347	Intermediate Similarity	NPC4286
0.8319	Intermediate Similarity	NPC469912
0.8319	Intermediate Similarity	NPC212965
0.8318	Intermediate Similarity	NPC260775
0.8305	Intermediate Similarity	NPC474131
0.8305	Intermediate Similarity	NPC135467
0.8305	Intermediate Similarity	NPC260832
0.8304	Intermediate Similarity	NPC19808
0.8304	Intermediate Similarity	NPC33728
0.8304	Intermediate Similarity	NPC473524
0.8291	Intermediate Similarity	NPC63010
0.8288	Intermediate Similarity	NPC61033
0.8288	Intermediate Similarity	NPC305603
0.8288	Intermediate Similarity	NPC320439
0.8276	Intermediate Similarity	NPC92
0.8276	Intermediate Similarity	NPC469663
0.8273	Intermediate Similarity	NPC117115
0.8273	Intermediate Similarity	NPC233396
0.8273	Intermediate Similarity	NPC154899
0.8269	Intermediate Similarity	NPC231150
0.825	Intermediate Similarity	NPC120638
0.8246	Intermediate Similarity	NPC473521
0.8246	Intermediate Similarity	NPC98372
0.8241	Intermediate Similarity	NPC130756
0.8241	Intermediate Similarity	NPC294741
0.8241	Intermediate Similarity	NPC12931
0.8241	Intermediate Similarity	NPC130103
0.8241	Intermediate Similarity	NPC70677
0.824	Intermediate Similarity	NPC472590
0.8235	Intermediate Similarity	NPC100108
0.8235	Intermediate Similarity	NPC277798
0.8235	Intermediate Similarity	NPC218753
0.8235	Intermediate Similarity	NPC129176
0.822	Intermediate Similarity	NPC32152
0.822	Intermediate Similarity	NPC472593
0.8214	Intermediate Similarity	NPC174981
0.8214	Intermediate Similarity	NPC306295
0.8211	Intermediate Similarity	NPC257947
0.8205	Intermediate Similarity	NPC477136
0.8205	Intermediate Similarity	NPC33270
0.8205	Intermediate Similarity	NPC69261
0.8205	Intermediate Similarity	NPC476266
0.8198	Intermediate Similarity	NPC469913
0.8198	Intermediate Similarity	NPC92623
0.8198	Intermediate Similarity	NPC135464
0.8197	Intermediate Similarity	NPC470726
0.819	Intermediate Similarity	NPC306884
0.819	Intermediate Similarity	NPC84999
0.819	Intermediate Similarity	NPC808
0.819	Intermediate Similarity	NPC147284
0.819	Intermediate Similarity	NPC192948
0.819	Intermediate Similarity	NPC35797
0.819	Intermediate Similarity	NPC246760
0.819	Intermediate Similarity	NPC210497
0.819	Intermediate Similarity	NPC94139
0.819	Intermediate Similarity	NPC3358
0.819	Intermediate Similarity	NPC162314
0.8182	Intermediate Similarity	NPC96940
0.8182	Intermediate Similarity	NPC475580
0.8182	Intermediate Similarity	NPC272029
0.8174	Intermediate Similarity	NPC23804
0.8173	Intermediate Similarity	NPC47950
0.8173	Intermediate Similarity	NPC312304
0.8173	Intermediate Similarity	NPC192
0.8167	Intermediate Similarity	NPC168707
0.8167	Intermediate Similarity	NPC48623
0.8165	Intermediate Similarity	NPC12221
0.8158	Intermediate Similarity	NPC77772
0.8158	Intermediate Similarity	NPC470770
0.8158	Intermediate Similarity	NPC266937
0.8151	Intermediate Similarity	NPC232295
0.8148	Intermediate Similarity	NPC128723
0.8136	Intermediate Similarity	NPC206205
0.8136	Intermediate Similarity	NPC329980
0.813	Intermediate Similarity	NPC470724
0.8125	Intermediate Similarity	NPC151477
0.812	Intermediate Similarity	NPC477137
0.812	Intermediate Similarity	NPC219112
0.812	Intermediate Similarity	NPC308828
0.812	Intermediate Similarity	NPC150624
0.812	Intermediate Similarity	NPC308311
0.812	Intermediate Similarity	NPC38893
0.8115	Intermediate Similarity	NPC117794
0.8113	Intermediate Similarity	NPC245187
0.8113	Intermediate Similarity	NPC152415
0.811	Intermediate Similarity	NPC472591
0.8103	Intermediate Similarity	NPC268160
0.8099	Intermediate Similarity	NPC152946
0.8091	Intermediate Similarity	NPC269212
0.8091	Intermediate Similarity	NPC242342
0.8091	Intermediate Similarity	NPC146798
0.8091	Intermediate Similarity	NPC313030
0.8091	Intermediate Similarity	NPC53051
0.8091	Intermediate Similarity	NPC302219
0.8091	Intermediate Similarity	NPC71002
0.8091	Intermediate Similarity	NPC24404
0.8091	Intermediate Similarity	NPC222522
0.8091	Intermediate Similarity	NPC94351
0.8091	Intermediate Similarity	NPC168303
0.8091	Intermediate Similarity	NPC249828
0.8091	Intermediate Similarity	NPC85479
0.8091	Intermediate Similarity	NPC106396
0.8087	Intermediate Similarity	NPC166995
0.8087	Intermediate Similarity	NPC177962
0.8087	Intermediate Similarity	NPC62867
0.8087	Intermediate Similarity	NPC228425
0.8087	Intermediate Similarity	NPC474920
0.8083	Intermediate Similarity	NPC45663

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 NPC228452 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	252
0.1-0.2	938
0.2-0.3	1549
0.3-0.4	2750
0.4-0.5	1812
0.5-0.6	1182
0.6-0.7	574
0.7-0.8	85
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8654	High Similarity	NPD288	Approved
0.8558	High Similarity	NPD844	Approved
0.8468	Intermediate Similarity	NPD4750	Phase 3
0.8241	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.819	Intermediate Similarity	NPD6671	Approved
0.8182	Intermediate Similarity	NPD4749	Approved
0.816	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.813	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8087	Intermediate Similarity	NPD7635	Approved
0.8019	Intermediate Similarity	NPD845	Approved
0.7982	Intermediate Similarity	NPD3020	Approved
0.7851	Intermediate Similarity	NPD4626	Approved
0.7838	Intermediate Similarity	NPD846	Approved
0.7838	Intermediate Similarity	NPD940	Approved
0.7805	Intermediate Similarity	NPD2232	Approved
0.7805	Intermediate Similarity	NPD2233	Approved
0.7805	Intermediate Similarity	NPD2230	Approved
0.7795	Intermediate Similarity	NPD4625	Phase 3
0.7778	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD2860	Approved
0.7706	Intermediate Similarity	NPD2859	Approved
0.7686	Intermediate Similarity	NPD3091	Approved
0.768	Intermediate Similarity	NPD6696	Suspended
0.7672	Intermediate Similarity	NPD3021	Approved
0.7672	Intermediate Similarity	NPD3022	Approved
0.7667	Intermediate Similarity	NPD7340	Approved
0.7652	Intermediate Similarity	NPD290	Approved
0.7652	Intermediate Similarity	NPD2342	Discontinued
0.7638	Intermediate Similarity	NPD2861	Phase 2
0.7623	Intermediate Similarity	NPD5691	Approved
0.7615	Intermediate Similarity	NPD2933	Approved
0.7615	Intermediate Similarity	NPD2934	Approved
0.7615	Intermediate Similarity	NPD2238	Phase 2
0.7586	Intermediate Similarity	NPD2684	Approved
0.7581	Intermediate Similarity	NPD1610	Phase 2
0.7578	Intermediate Similarity	NPD4908	Phase 1
0.7565	Intermediate Similarity	NPD1445	Approved
0.7565	Intermediate Similarity	NPD1444	Approved
0.7563	Intermediate Similarity	NPD1398	Phase 1
0.7545	Intermediate Similarity	NPD1809	Phase 2
0.7542	Intermediate Similarity	NPD228	Approved
0.7519	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD3496	Discontinued
0.75	Intermediate Similarity	NPD4097	Suspended
0.748	Intermediate Similarity	NPD3094	Phase 2
0.7462	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD596	Approved
0.7442	Intermediate Similarity	NPD600	Approved
0.744	Intermediate Similarity	NPD3092	Approved
0.7438	Intermediate Similarity	NPD7157	Approved
0.7419	Intermediate Similarity	NPD1778	Approved
0.7417	Intermediate Similarity	NPD5283	Phase 1
0.7414	Intermediate Similarity	NPD968	Approved
0.7381	Intermediate Similarity	NPD2231	Phase 2
0.7381	Intermediate Similarity	NPD2235	Phase 2
0.7373	Intermediate Similarity	NPD1792	Phase 2
0.7348	Intermediate Similarity	NPD4060	Phase 1
0.7333	Intermediate Similarity	NPD6099	Approved
0.7333	Intermediate Similarity	NPD6100	Approved
0.7333	Intermediate Similarity	NPD7843	Approved
0.7302	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD4624	Approved
0.7281	Intermediate Similarity	NPD1242	Phase 1
0.728	Intermediate Similarity	NPD2668	Approved
0.728	Intermediate Similarity	NPD3095	Discontinued
0.728	Intermediate Similarity	NPD4059	Approved
0.728	Intermediate Similarity	NPD2667	Approved
0.7273	Intermediate Similarity	NPD840	Approved
0.7273	Intermediate Similarity	NPD839	Approved
0.7273	Intermediate Similarity	NPD2228	Approved
0.7273	Intermediate Similarity	NPD2229	Approved
0.7273	Intermediate Similarity	NPD2234	Approved
0.7264	Intermediate Similarity	NPD111	Approved
0.7258	Intermediate Similarity	NPD1548	Phase 1
0.725	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD9493	Approved
0.7231	Intermediate Similarity	NPD1712	Approved
0.7231	Intermediate Similarity	NPD2237	Approved
0.7218	Intermediate Similarity	NPD1613	Approved
0.7218	Intermediate Similarity	NPD3620	Phase 2
0.7218	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD9618	Approved
0.7213	Intermediate Similarity	NPD9614	Approved
0.7209	Intermediate Similarity	NPD2797	Approved
0.719	Intermediate Similarity	NPD1138	Approved
0.7174	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5177	Phase 3
0.7165	Intermediate Similarity	NPD1091	Approved
0.7155	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD3691	Phase 2
0.7154	Intermediate Similarity	NPD709	Approved
0.7154	Intermediate Similarity	NPD3690	Phase 2
0.7154	Intermediate Similarity	NPD6584	Phase 3
0.7143	Intermediate Similarity	NPD2932	Approved
0.7143	Intermediate Similarity	NPD3019	Approved
0.7132	Intermediate Similarity	NPD1283	Approved
0.7131	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6653	Approved
0.7107	Intermediate Similarity	NPD1139	Approved
0.7107	Intermediate Similarity	NPD1137	Approved
0.7105	Intermediate Similarity	NPD9273	Approved
0.7099	Intermediate Similarity	NPD5736	Approved
0.7097	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD4140	Approved
0.708	Intermediate Similarity	NPD2935	Discontinued
0.7073	Intermediate Similarity	NPD497	Approved
0.7063	Intermediate Similarity	NPD1651	Approved
0.7063	Intermediate Similarity	NPD5585	Approved
0.7063	Intermediate Similarity	NPD1357	Approved
0.7054	Intermediate Similarity	NPD5327	Phase 3
0.7049	Intermediate Similarity	NPD821	Approved
0.7045	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD9613	Approved
0.704	Intermediate Similarity	NPD9616	Approved
0.704	Intermediate Similarity	NPD9615	Approved
0.7037	Intermediate Similarity	NPD5735	Approved
0.7031	Intermediate Similarity	NPD1611	Approved
0.7029	Intermediate Similarity	NPD5763	Approved
0.7029	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD9295	Approved
0.6992	Remote Similarity	NPD496	Approved
0.6992	Remote Similarity	NPD495	Approved
0.6992	Remote Similarity	NPD498	Approved
0.6985	Remote Similarity	NPD2157	Approved
0.6985	Remote Similarity	NPD6353	Approved
0.6984	Remote Similarity	NPD316	Approved
0.6984	Remote Similarity	NPD7741	Discontinued
0.6984	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3134	Approved
0.697	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5451	Approved
0.694	Remote Similarity	NPD3268	Approved
0.6935	Remote Similarity	NPD1793	Approved
0.6935	Remote Similarity	NPD1791	Approved
0.6929	Remote Similarity	NPD4093	Discontinued
0.6929	Remote Similarity	NPD3443	Approved
0.6929	Remote Similarity	NPD3444	Approved
0.6929	Remote Similarity	NPD3445	Approved
0.6923	Remote Similarity	NPD3685	Discontinued
0.6923	Remote Similarity	NPD6582	Phase 2
0.6923	Remote Similarity	NPD6583	Phase 3
0.6906	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6004	Phase 3
0.6906	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6002	Phase 3
0.6906	Remote Similarity	NPD6005	Phase 3
0.6905	Remote Similarity	NPD7644	Approved
0.6899	Remote Similarity	NPD1281	Approved
0.6899	Remote Similarity	NPD422	Phase 1
0.6894	Remote Similarity	NPD558	Phase 2
0.6889	Remote Similarity	NPD6663	Approved
0.688	Remote Similarity	NPD4198	Discontinued
0.688	Remote Similarity	NPD2557	Approved
0.688	Remote Similarity	NPD6387	Discontinued
0.6879	Remote Similarity	NPD3892	Phase 2
0.6875	Remote Similarity	NPD5126	Approved
0.6875	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2286	Discontinued
0.6875	Remote Similarity	NPD1751	Approved
0.6875	Remote Similarity	NPD5125	Phase 3
0.6875	Remote Similarity	NPD6090	Discontinued
0.687	Remote Similarity	NPD8651	Approved
0.6864	Remote Similarity	NPD9500	Approved
0.6857	Remote Similarity	NPD2424	Discontinued
0.6853	Remote Similarity	NPD7041	Phase 2
0.6853	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.685	Remote Similarity	NPD5304	Approved
0.685	Remote Similarity	NPD5303	Approved
0.6849	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1608	Approved
0.6838	Remote Similarity	NPD2979	Phase 3
0.6827	Remote Similarity	NPD9294	Approved
0.6818	Remote Similarity	NPD1133	Approved
0.6818	Remote Similarity	NPD1129	Approved
0.6818	Remote Similarity	NPD6362	Approved
0.6818	Remote Similarity	NPD1134	Approved
0.6818	Remote Similarity	NPD1131	Approved
0.6818	Remote Similarity	NPD1135	Approved
0.6815	Remote Similarity	NPD7985	Registered
0.6812	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6674	Discontinued
0.6803	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1669	Approved
0.6794	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD4359	Approved
0.6788	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6355	Discontinued
0.6788	Remote Similarity	NPD5124	Phase 1
0.6769	Remote Similarity	NPD3705	Approved
0.6769	Remote Similarity	NPD1201	Approved
0.6767	Remote Similarity	NPD602	Approved
0.6767	Remote Similarity	NPD599	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