NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	252.17
Volume:	277.901
LogP:	2.882
LogD:	2.898
LogS:	-3.174
# Rotatable Bonds:	6
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.729
Synthetic Accessibility Score:	2.898
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.286
MDCK Permeability:	2.0697822037618607e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.039

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.507
Plasma Protein Binding (PPB):	63.79749298095703%
Volume Distribution (VD):	3.514
Pgp-substrate:	41.987186431884766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.418
CYP1A2-substrate:	0.402
CYP2C19-inhibitor:	0.214
CYP2C19-substrate:	0.806
CYP2C9-inhibitor:	0.321
CYP2C9-substrate:	0.697
CYP2D6-inhibitor:	0.358
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.38
CYP3A4-substrate:	0.456

ADMET: Excretion

Clearance (CL):	13.231
Half-life (T1/2):	0.7

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.042
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.073
Skin Sensitization:	0.408
Carcinogencity:	0.037
Eye Corrosion:	0.006
Eye Irritation:	0.73
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC66834

Natural Product ID:	NPC66834
*Common Name:**	(S)-(+)-Sydonol
IUPAC Name:	5-(hydroxymethyl)-2-[(2S)-2-hydroxy-6-methylheptan-2-yl]phenol
Synonyms:
Standard InCHIKey:	YOBQORBMRZQKGS-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C15H24O3/c1-11(2)5-4-8-15(3,18)13-7-6-12(10-16)9-14(13)17/h6-7,9,11,16-18H,4-5,8,10H2,1-3H3/t15-/m0/s1
SMILES:	OCc1ccc(c(c1)O)[C@](CCCC(C)C)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2397439
PubChem CID:	25112062
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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	<=	48.0	%	PMID[510930]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	324.6	mg/dl	PMID[510930]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	65.29	%	PMID[510930]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16390.0	nM	PMID[510930]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	86.99	%	PMID[510930]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5230.0	nM	PMID[510930]

☑ 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 NPC66834 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	257
0.1-0.2	1296
0.2-0.3	3717
0.3-0.4	12377
0.4-0.5	7656
0.5-0.6	9887
0.6-0.7	5803
0.7-0.8	1381
0.8-0.85	219
0.85-0.9	83
0.9-0.95	16
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC475225
0.9596	High Similarity	NPC471228
0.9596	High Similarity	NPC235762
0.9519	High Similarity	NPC228452
0.9394	High Similarity	NPC174911
0.9394	High Similarity	NPC72729
0.9192	High Similarity	NPC79241
0.9192	High Similarity	NPC6597
0.9151	High Similarity	NPC302371
0.9091	High Similarity	NPC259512
0.9091	High Similarity	NPC312132
0.9	High Similarity	NPC474073
0.8962	High Similarity	NPC132720
0.8942	High Similarity	NPC53740
0.8919	High Similarity	NPC151197
0.8911	High Similarity	NPC299762
0.8911	High Similarity	NPC33675
0.8909	High Similarity	NPC320864
0.8889	High Similarity	NPC319803
0.8857	High Similarity	NPC474352
0.8846	High Similarity	NPC47284
0.8846	High Similarity	NPC471350
0.8812	High Similarity	NPC88420
0.8762	High Similarity	NPC310456
0.875	High Similarity	NPC218879
0.875	High Similarity	NPC244513
0.875	High Similarity	NPC323810
0.875	High Similarity	NPC227458
0.875	High Similarity	NPC160235
0.8738	High Similarity	NPC80800
0.8738	High Similarity	NPC477685
0.8738	High Similarity	NPC252105
0.8716	High Similarity	NPC261343
0.8704	High Similarity	NPC224527
0.8704	High Similarity	NPC54373
0.8692	High Similarity	NPC186385
0.8692	High Similarity	NPC473524
0.8692	High Similarity	NPC299568
0.8687	High Similarity	NPC231150
0.8679	High Similarity	NPC158253
0.8679	High Similarity	NPC204901
0.8679	High Similarity	NPC232523
0.8673	High Similarity	NPC328485
0.8667	High Similarity	NPC37802
0.8661	High Similarity	NPC48781
0.8661	High Similarity	NPC9592
0.8654	High Similarity	NPC108497
0.8641	High Similarity	NPC129373
0.8641	High Similarity	NPC248396
0.8641	High Similarity	NPC48730
0.8641	High Similarity	NPC130103
0.8627	High Similarity	NPC152097
0.8627	High Similarity	NPC475078
0.8624	High Similarity	NPC26615
0.8624	High Similarity	NPC473521
0.8598	High Similarity	NPC174981
0.8598	High Similarity	NPC306295
0.8586	High Similarity	NPC312304
0.8586	High Similarity	NPC47950
0.8585	High Similarity	NPC99836
0.8585	High Similarity	NPC12640
0.8585	High Similarity	NPC201662
0.8571	High Similarity	NPC130817
0.8571	High Similarity	NPC475580
0.8571	High Similarity	NPC272029
0.8559	High Similarity	NPC474486
0.8559	High Similarity	NPC232165
0.8558	High Similarity	NPC12221
0.8545	High Similarity	NPC190212
0.8544	High Similarity	NPC128723
0.8544	High Similarity	NPC260775
0.8534	High Similarity	NPC261992
0.8532	High Similarity	NPC469912
0.8519	High Similarity	NPC19808
0.8519	High Similarity	NPC33728
0.8515	High Similarity	NPC245187
0.8515	High Similarity	NPC152415
0.8505	High Similarity	NPC305603
0.8505	High Similarity	NPC61033
0.8505	High Similarity	NPC320439
0.8491	Intermediate Similarity	NPC117115
0.8482	Intermediate Similarity	NPC92
0.8482	Intermediate Similarity	NPC469663
0.8476	Intermediate Similarity	NPC269212
0.8462	Intermediate Similarity	NPC117794
0.8462	Intermediate Similarity	NPC70677
0.8462	Intermediate Similarity	NPC130756
0.8462	Intermediate Similarity	NPC12931
0.8462	Intermediate Similarity	NPC294741
0.8448	Intermediate Similarity	NPC188997
0.8447	Intermediate Similarity	NPC77492
0.8426	Intermediate Similarity	NPC64586
0.8416	Intermediate Similarity	NPC3358
0.8416	Intermediate Similarity	NPC306884
0.8416	Intermediate Similarity	NPC94139
0.8416	Intermediate Similarity	NPC55903
0.8416	Intermediate Similarity	NPC210497
0.8416	Intermediate Similarity	NPC29373
0.8416	Intermediate Similarity	NPC147284
0.8416	Intermediate Similarity	NPC162314
0.8411	Intermediate Similarity	NPC469913
0.8411	Intermediate Similarity	NPC21594
0.8407	Intermediate Similarity	NPC477136
0.84	Intermediate Similarity	NPC192
0.8393	Intermediate Similarity	NPC84999
0.8393	Intermediate Similarity	NPC35797
0.8393	Intermediate Similarity	NPC192948
0.8393	Intermediate Similarity	NPC246760
0.839	Intermediate Similarity	NPC472592
0.8384	Intermediate Similarity	NPC1793
0.8384	Intermediate Similarity	NPC27974
0.8378	Intermediate Similarity	NPC23804
0.8364	Intermediate Similarity	NPC77772
0.8364	Intermediate Similarity	NPC470770
0.8364	Intermediate Similarity	NPC266937
0.8349	Intermediate Similarity	NPC58865
0.8333	Intermediate Similarity	NPC151477
0.8319	Intermediate Similarity	NPC219112
0.8319	Intermediate Similarity	NPC308311
0.8319	Intermediate Similarity	NPC38893
0.8319	Intermediate Similarity	NPC477137
0.8319	Intermediate Similarity	NPC308828
0.8317	Intermediate Similarity	NPC306074
0.8317	Intermediate Similarity	NPC304541
0.8304	Intermediate Similarity	NPC268160
0.8304	Intermediate Similarity	NPC41851
0.8302	Intermediate Similarity	NPC222522
0.8302	Intermediate Similarity	NPC168303
0.8302	Intermediate Similarity	NPC302219
0.8302	Intermediate Similarity	NPC242342
0.8302	Intermediate Similarity	NPC53051
0.8302	Intermediate Similarity	NPC24404
0.8302	Intermediate Similarity	NPC249828
0.8302	Intermediate Similarity	NPC146798
0.8302	Intermediate Similarity	NPC313030
0.8302	Intermediate Similarity	NPC71002
0.8302	Intermediate Similarity	NPC85479
0.8302	Intermediate Similarity	NPC94351
0.8302	Intermediate Similarity	NPC168393
0.8302	Intermediate Similarity	NPC106396
0.8291	Intermediate Similarity	NPC325301
0.8291	Intermediate Similarity	NPC327070
0.8288	Intermediate Similarity	NPC228425
0.8288	Intermediate Similarity	NPC62867
0.8288	Intermediate Similarity	NPC166995
0.8288	Intermediate Similarity	NPC177962
0.8286	Intermediate Similarity	NPC10588
0.8286	Intermediate Similarity	NPC166761
0.8283	Intermediate Similarity	NPC407
0.8283	Intermediate Similarity	NPC307235
0.8273	Intermediate Similarity	NPC224870
0.8261	Intermediate Similarity	NPC121866
0.8261	Intermediate Similarity	NPC469644
0.8257	Intermediate Similarity	NPC262365
0.8257	Intermediate Similarity	NPC241549
0.8252	Intermediate Similarity	NPC222146
0.8252	Intermediate Similarity	NPC8392
0.8246	Intermediate Similarity	NPC304510
0.8246	Intermediate Similarity	NPC172219
0.8241	Intermediate Similarity	NPC67250
0.8241	Intermediate Similarity	NPC155072
0.8235	Intermediate Similarity	NPC325292
0.8235	Intermediate Similarity	NPC138117
0.823	Intermediate Similarity	NPC147179
0.8224	Intermediate Similarity	NPC102216
0.8224	Intermediate Similarity	NPC238696
0.8218	Intermediate Similarity	NPC300017
0.8214	Intermediate Similarity	NPC263753
0.8214	Intermediate Similarity	NPC117846
0.8208	Intermediate Similarity	NPC166313
0.8208	Intermediate Similarity	NPC284011
0.8208	Intermediate Similarity	NPC147310
0.8208	Intermediate Similarity	NPC294186
0.8208	Intermediate Similarity	NPC137415
0.8208	Intermediate Similarity	NPC192032
0.8208	Intermediate Similarity	NPC11280
0.8208	Intermediate Similarity	NPC72947
0.8208	Intermediate Similarity	NPC24407
0.8205	Intermediate Similarity	NPC25168
0.8198	Intermediate Similarity	NPC151537
0.8198	Intermediate Similarity	NPC275627
0.819	Intermediate Similarity	NPC223451
0.819	Intermediate Similarity	NPC122005
0.819	Intermediate Similarity	NPC252821
0.8182	Intermediate Similarity	NPC155393
0.8182	Intermediate Similarity	NPC98392
0.8174	Intermediate Similarity	NPC283616
0.8174	Intermediate Similarity	NPC471671
0.8174	Intermediate Similarity	NPC469609
0.8174	Intermediate Similarity	NPC154030
0.8174	Intermediate Similarity	NPC206
0.8174	Intermediate Similarity	NPC206205
0.8165	Intermediate Similarity	NPC233320
0.8158	Intermediate Similarity	NPC141001
0.8155	Intermediate Similarity	NPC316301
0.8155	Intermediate Similarity	NPC76938
0.8155	Intermediate Similarity	NPC27323
0.8155	Intermediate Similarity	NPC289769
0.8151	Intermediate Similarity	NPC174729
0.8151	Intermediate Similarity	NPC139774

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 NPC66834 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	931
0.2-0.3	1509
0.3-0.4	2905
0.4-0.5	1813
0.5-0.6	1204
0.6-0.7	471
0.7-0.8	69
0.8-0.85	5
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD288	Approved
0.899	High Similarity	NPD844	Approved
0.8692	High Similarity	NPD4750	Phase 3
0.8641	High Similarity	NPD289	Clinical (unspecified phase)
0.8416	Intermediate Similarity	NPD845	Approved
0.8288	Intermediate Similarity	NPD7635	Approved
0.8208	Intermediate Similarity	NPD846	Approved
0.8208	Intermediate Similarity	NPD940	Approved
0.819	Intermediate Similarity	NPD3020	Approved
0.8155	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7909	Intermediate Similarity	NPD1444	Approved
0.7909	Intermediate Similarity	NPD1445	Approved
0.7905	Intermediate Similarity	NPD1809	Phase 2
0.7905	Intermediate Similarity	NPD2859	Approved
0.7905	Intermediate Similarity	NPD2860	Approved
0.7863	Intermediate Similarity	NPD3091	Approved
0.7857	Intermediate Similarity	NPD3021	Approved
0.7857	Intermediate Similarity	NPD3022	Approved
0.7838	Intermediate Similarity	NPD2342	Discontinued
0.781	Intermediate Similarity	NPD2934	Approved
0.781	Intermediate Similarity	NPD2933	Approved
0.7769	Intermediate Similarity	NPD4749	Approved
0.776	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD6671	Approved
0.7724	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD1792	Phase 2
0.7642	Intermediate Similarity	NPD3094	Phase 2
0.7624	Intermediate Similarity	NPD111	Approved
0.7615	Intermediate Similarity	NPD1242	Phase 1
0.7603	Intermediate Similarity	NPD3092	Approved
0.7521	Intermediate Similarity	NPD9618	Approved
0.7521	Intermediate Similarity	NPD9614	Approved
0.7459	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4626	Approved
0.7438	Intermediate Similarity	NPD4059	Approved
0.7438	Intermediate Similarity	NPD3095	Discontinued
0.7436	Intermediate Similarity	NPD2229	Approved
0.7436	Intermediate Similarity	NPD2228	Approved
0.7436	Intermediate Similarity	NPD2234	Approved
0.7431	Intermediate Similarity	NPD9273	Approved
0.7414	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD4625	Phase 3
0.7398	Intermediate Similarity	NPD2232	Approved
0.7398	Intermediate Similarity	NPD2230	Approved
0.7398	Intermediate Similarity	NPD2233	Approved
0.7373	Intermediate Similarity	NPD497	Approved
0.7368	Intermediate Similarity	NPD290	Approved
0.7339	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9616	Approved
0.7333	Intermediate Similarity	NPD9615	Approved
0.7333	Intermediate Similarity	NPD9613	Approved
0.7321	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1610	Phase 2
0.7295	Intermediate Similarity	NPD2932	Approved
0.7295	Intermediate Similarity	NPD3019	Approved
0.7288	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD495	Approved
0.7288	Intermediate Similarity	NPD498	Approved
0.7288	Intermediate Similarity	NPD1398	Phase 1
0.7288	Intermediate Similarity	NPD496	Approved
0.728	Intermediate Similarity	NPD6696	Suspended
0.7273	Intermediate Similarity	NPD316	Approved
0.7265	Intermediate Similarity	NPD228	Approved
0.725	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7340	Approved
0.7244	Intermediate Similarity	NPD2861	Phase 2
0.7231	Intermediate Similarity	NPD2238	Phase 2
0.7227	Intermediate Similarity	NPD1793	Approved
0.7227	Intermediate Similarity	NPD1791	Approved
0.7213	Intermediate Similarity	NPD5691	Approved
0.7188	Intermediate Similarity	NPD600	Approved
0.7188	Intermediate Similarity	NPD596	Approved
0.7188	Intermediate Similarity	NPD4908	Phase 1
0.7172	Intermediate Similarity	NPD9294	Approved
0.7168	Intermediate Similarity	NPD9500	Approved
0.7155	Intermediate Similarity	NPD2684	Approved
0.7154	Intermediate Similarity	NPD1751	Approved
0.7154	Intermediate Similarity	NPD1778	Approved
0.7132	Intermediate Similarity	NPD3027	Phase 3
0.7131	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD968	Approved
0.7121	Intermediate Similarity	NPD4097	Suspended
0.7109	Intermediate Similarity	NPD5736	Approved
0.7097	Intermediate Similarity	NPD3496	Discontinued
0.7094	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1134	Approved
0.7087	Intermediate Similarity	NPD1129	Approved
0.7087	Intermediate Similarity	NPD1135	Approved
0.7087	Intermediate Similarity	NPD1131	Approved
0.7087	Intermediate Similarity	NPD1133	Approved
0.7083	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4093	Discontinued
0.704	Intermediate Similarity	NPD1201	Approved
0.7031	Intermediate Similarity	NPD599	Approved
0.7031	Intermediate Similarity	NPD602	Approved
0.7031	Intermediate Similarity	NPD858	Approved
0.7031	Intermediate Similarity	NPD859	Approved
0.7025	Intermediate Similarity	NPD7157	Approved
0.7023	Intermediate Similarity	NPD840	Approved
0.7023	Intermediate Similarity	NPD839	Approved
0.7016	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD9381	Approved
0.7016	Intermediate Similarity	NPD2286	Discontinued
0.7016	Intermediate Similarity	NPD9384	Approved
0.7	Intermediate Similarity	NPD5283	Phase 1
0.6992	Remote Similarity	NPD5303	Approved
0.6992	Remote Similarity	NPD5304	Approved
0.6992	Remote Similarity	NPD1548	Phase 1
0.6984	Remote Similarity	NPD2235	Phase 2
0.6984	Remote Similarity	NPD2231	Phase 2
0.6977	Remote Similarity	NPD1712	Approved
0.697	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1613	Approved
0.697	Remote Similarity	NPD4060	Phase 1
0.6967	Remote Similarity	NPD9493	Approved
0.6967	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6100	Approved
0.6963	Remote Similarity	NPD6099	Approved
0.6957	Remote Similarity	NPD9610	Approved
0.6957	Remote Similarity	NPD9608	Approved
0.6931	Remote Similarity	NPD9088	Approved
0.6929	Remote Similarity	NPD9622	Approved
0.6917	Remote Similarity	NPD9379	Approved
0.6917	Remote Similarity	NPD1138	Approved
0.6917	Remote Similarity	NPD7843	Approved
0.6917	Remote Similarity	NPD9377	Approved
0.6911	Remote Similarity	NPD16	Approved
0.6911	Remote Similarity	NPD856	Approved
0.6905	Remote Similarity	NPD1091	Approved
0.6899	Remote Similarity	NPD4624	Approved
0.6894	Remote Similarity	NPD6663	Approved
0.6889	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD709	Approved
0.688	Remote Similarity	NPD2667	Approved
0.688	Remote Similarity	NPD4589	Approved
0.688	Remote Similarity	NPD2668	Approved
0.6875	Remote Similarity	NPD1283	Approved
0.6869	Remote Similarity	NPD9087	Approved
0.6864	Remote Similarity	NPD9266	Approved
0.6864	Remote Similarity	NPD74	Approved
0.686	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1759	Phase 1
0.6846	Remote Similarity	NPD2237	Approved
0.6842	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3028	Approved
0.6842	Remote Similarity	NPD3620	Phase 2
0.6842	Remote Similarity	NPD1616	Discontinued
0.6833	Remote Similarity	NPD1137	Approved
0.6833	Remote Similarity	NPD1139	Approved
0.6827	Remote Similarity	NPD9089	Approved
0.6825	Remote Similarity	NPD1981	Approved
0.6825	Remote Similarity	NPD1983	Approved
0.6825	Remote Similarity	NPD1980	Approved
0.6822	Remote Similarity	NPD1470	Approved
0.6822	Remote Similarity	NPD4103	Phase 2
0.6822	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD2797	Approved
0.6822	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD5177	Phase 3
0.6803	Remote Similarity	NPD475	Phase 2
0.68	Remote Similarity	NPD1357	Approved
0.68	Remote Similarity	NPD1651	Approved
0.6797	Remote Similarity	NPD4659	Approved
0.6797	Remote Similarity	NPD1755	Approved
0.6794	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.678	Remote Similarity	NPD9263	Approved
0.678	Remote Similarity	NPD9267	Approved
0.678	Remote Similarity	NPD9264	Approved
0.6777	Remote Similarity	NPD821	Approved
0.6774	Remote Similarity	NPD1758	Phase 1
0.6774	Remote Similarity	NPD318	Approved
0.6774	Remote Similarity	NPD317	Approved
0.6772	Remote Similarity	NPD1611	Approved
0.6769	Remote Similarity	NPD9621	Approved
0.6769	Remote Similarity	NPD6584	Phase 3
0.6769	Remote Similarity	NPD2194	Approved
0.6769	Remote Similarity	NPD2195	Approved
0.6769	Remote Similarity	NPD9619	Approved
0.6769	Remote Similarity	NPD3690	Phase 2
0.6769	Remote Similarity	NPD3691	Phase 2
0.6769	Remote Similarity	NPD9620	Approved
0.6767	Remote Similarity	NPD6407	Approved
0.6767	Remote Similarity	NPD6405	Approved
0.6765	Remote Similarity	NPD7743	Approved
0.6765	Remote Similarity	NPD7742	Approved
0.6763	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1101	Approved
0.675	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD2568	Approved
0.6741	Remote Similarity	NPD6653	Approved
0.6731	Remote Similarity	NPD9093	Approved
0.672	Remote Similarity	NPD7330	Discontinued
0.6718	Remote Similarity	NPD3635	Approved
0.6718	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD3636	Approved
0.6718	Remote Similarity	NPD3637	Approved
0.6716	Remote Similarity	NPD4140	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