NPASS Compound

Structure

NPC469699 OpenBabel07101719132D 29 32 0 0 1 0 0 0 0 0999 V2000 -1.1340 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8690 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1369 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 16 1 0 0 0 0 5 10 1 0 0 0 0 5 11 2 0 0 0 0 6 11 1 0 0 0 0 6 13 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 22 1 0 0 0 0 10 14 2 0 0 0 0 11 12 1 0 0 0 0 13 21 1 6 0 0 0 14 27 1 0 0 0 0 15 9 1 6 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 23 2 0 0 0 0 16 27 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 1 0 0 0 18 19 1 0 0 0 0 18 25 1 6 0 0 0 19 20 1 0 0 0 0 19 26 1 1 0 0 0 20 28 1 0 0 0 0 20 29 1 6 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.16
Volume:	394.686
LogP:	1.265
LogD:	1.172
LogS:	-3.093
# Rotatable Bonds:	4
TPSA:	129.59
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.526
Synthetic Accessibility Score:	4.25
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.296
MDCK Permeability:	1.325810171692865e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.34
20% Bioavailability (F20%):	0.048
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	89.26553344726562%
Volume Distribution (VD):	0.817
Pgp-substrate:	9.999950408935547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.096
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.27
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.199
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.409
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.08

ADMET: Excretion

Clearance (CL):	4.028
Half-life (T1/2):	0.485

ADMET: Toxicity

hERG Blockers:	0.096
Human Hepatotoxicity (H-HT):	0.23
Drug-inuced Liver Injury (DILI):	0.543
AMES Toxicity:	0.077
Rat Oral Acute Toxicity:	0.144
Maximum Recommended Daily Dose:	0.864
Skin Sensitization:	0.158
Carcinogencity:	0.495
Eye Corrosion:	0.003
Eye Irritation:	0.078
Respiratory Toxicity:	0.025

Download Data

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

Natural Product: NPC469699

Natural Product ID:	NPC469699
*Common Name:**	(S)-2-[1-Methyl-1-(3,4,5-Trihydroxy-6-Hydroxymethyl-Tetrahydro-Pyran-2-Yloxy)-Ethyl]-2,3-Dihydro-Furo[3,2-G]Chromen-7-One
IUPAC Name:	(7R)-7-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]-7,8-dihydro-6H-cyclopenta[g]chromen-2-one
Synonyms:
Standard InCHIKey:	BPGKEPWWWHYAHB-HUFJVISLSA-N
Standard InCHI:	InChI=1S/C21H26O8/c1-21(2,29-20-19(26)18(25)17(24)15(9-22)28-20)13-6-11-5-10-3-4-16(23)27-14(10)8-12(11)7-13/h3-5,8,13,15,17-20,22,24-26H,6-7,9H2,1-2H3/t13-,15-,17-,18+,19-,20+/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC([C@H]2Cc3c(C2)cc2c(c3)oc(=O)cc2)(C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1159421
PubChem CID:	46905093
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO3509	Angelica furcijuga	Species	Apiaceae	Eukaryota	roots	Miyazaki prefecture, Japan	n.a.	PMID[9873511]
NPO3509	Angelica furcijuga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3509	Angelica furcijuga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3509	Angelica furcijuga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	2
Others	2

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	IC50	>	100000.0	nM	PMID[544909]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	16.0	%	PMID[544909]
NPT32	Organism	Mus musculus	Mus musculus	IC50	>	100000.0	nM	PMID[544909]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	49.0	%	PMID[544909]

☑ 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 NPC469699 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	370
0.1-0.2	1524
0.2-0.3	2993
0.3-0.4	6903
0.4-0.5	10697
0.5-0.6	5738
0.6-0.7	6508
0.7-0.8	7490
0.8-0.85	455
0.85-0.9	18
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8933	High Similarity	NPC296377
0.8926	High Similarity	NPC85624
0.8874	High Similarity	NPC169510
0.8874	High Similarity	NPC95990
0.8808	High Similarity	NPC87950
0.8808	High Similarity	NPC471764
0.8766	High Similarity	NPC470264
0.8642	High Similarity	NPC208818
0.8627	High Similarity	NPC308178
0.8609	High Similarity	NPC478240
0.8553	High Similarity	NPC469701
0.8543	High Similarity	NPC263397
0.8543	High Similarity	NPC302286
0.8543	High Similarity	NPC116104
0.8543	High Similarity	NPC88754
0.8543	High Similarity	NPC237872
0.8533	High Similarity	NPC287286
0.8533	High Similarity	NPC476442
0.8533	High Similarity	NPC215512
0.8516	High Similarity	NPC147224
0.8506	High Similarity	NPC130959
0.8506	High Similarity	NPC474795
0.8506	High Similarity	NPC159697
0.8506	High Similarity	NPC303013
0.8506	High Similarity	NPC474940
0.8467	Intermediate Similarity	NPC312881
0.8462	Intermediate Similarity	NPC478249
0.8462	Intermediate Similarity	NPC77310
0.8462	Intermediate Similarity	NPC269914
0.8456	Intermediate Similarity	NPC153818
0.8456	Intermediate Similarity	NPC232246
0.8438	Intermediate Similarity	NPC478269
0.8428	Intermediate Similarity	NPC228357
0.8414	Intermediate Similarity	NPC295970
0.8411	Intermediate Similarity	NPC195357
0.8411	Intermediate Similarity	NPC152771
0.8408	Intermediate Similarity	NPC302610
0.84	Intermediate Similarity	NPC279573
0.8389	Intermediate Similarity	NPC103409
0.8389	Intermediate Similarity	NPC224543
0.8389	Intermediate Similarity	NPC78746
0.8389	Intermediate Similarity	NPC188380
0.8387	Intermediate Similarity	NPC93924
0.8387	Intermediate Similarity	NPC96294
0.8377	Intermediate Similarity	NPC37838
0.8366	Intermediate Similarity	NPC217635
0.8366	Intermediate Similarity	NPC251062
0.8366	Intermediate Similarity	NPC184464
0.8366	Intermediate Similarity	NPC471667
0.8366	Intermediate Similarity	NPC79429
0.8355	Intermediate Similarity	NPC145319
0.8354	Intermediate Similarity	NPC229548
0.8354	Intermediate Similarity	NPC478241
0.8354	Intermediate Similarity	NPC89693
0.8344	Intermediate Similarity	NPC475379
0.8333	Intermediate Similarity	NPC475940
0.8333	Intermediate Similarity	NPC184861
0.8333	Intermediate Similarity	NPC155963
0.8333	Intermediate Similarity	NPC281014
0.8333	Intermediate Similarity	NPC225106
0.8333	Intermediate Similarity	NPC474893
0.8333	Intermediate Similarity	NPC294456
0.8333	Intermediate Similarity	NPC212124
0.8333	Intermediate Similarity	NPC478267
0.8333	Intermediate Similarity	NPC181452
0.8333	Intermediate Similarity	NPC220006
0.8323	Intermediate Similarity	NPC52740
0.8323	Intermediate Similarity	NPC241600
0.8323	Intermediate Similarity	NPC173726
0.8322	Intermediate Similarity	NPC472525
0.8313	Intermediate Similarity	NPC478248
0.8312	Intermediate Similarity	NPC43508
0.8312	Intermediate Similarity	NPC226722
0.8312	Intermediate Similarity	NPC476301
0.8303	Intermediate Similarity	NPC286809
0.8291	Intermediate Similarity	NPC169404
0.8291	Intermediate Similarity	NPC476452
0.8291	Intermediate Similarity	NPC476352
0.8291	Intermediate Similarity	NPC53587
0.8291	Intermediate Similarity	NPC215060
0.8291	Intermediate Similarity	NPC474442
0.8291	Intermediate Similarity	NPC176186
0.8289	Intermediate Similarity	NPC137501
0.8289	Intermediate Similarity	NPC154262
0.8289	Intermediate Similarity	NPC7518
0.8289	Intermediate Similarity	NPC159387
0.828	Intermediate Similarity	NPC114740
0.8278	Intermediate Similarity	NPC211110
0.8278	Intermediate Similarity	NPC49597
0.8278	Intermediate Similarity	NPC151946
0.8269	Intermediate Similarity	NPC117788
0.8269	Intermediate Similarity	NPC290902
0.8269	Intermediate Similarity	NPC220282
0.8269	Intermediate Similarity	NPC474856
0.8269	Intermediate Similarity	NPC291326
0.8269	Intermediate Similarity	NPC474834
0.8267	Intermediate Similarity	NPC37468
0.8267	Intermediate Similarity	NPC38099
0.8267	Intermediate Similarity	NPC26954
0.8267	Intermediate Similarity	NPC166180
0.8258	Intermediate Similarity	NPC199928
0.8255	Intermediate Similarity	NPC180716
0.8255	Intermediate Similarity	NPC62366
0.8255	Intermediate Similarity	NPC211164
0.8255	Intermediate Similarity	NPC213173
0.8255	Intermediate Similarity	NPC224475
0.8247	Intermediate Similarity	NPC296659
0.8247	Intermediate Similarity	NPC292443
0.8247	Intermediate Similarity	NPC202391
0.8247	Intermediate Similarity	NPC164183
0.8247	Intermediate Similarity	NPC232228
0.8239	Intermediate Similarity	NPC150442
0.8239	Intermediate Similarity	NPC257847
0.8228	Intermediate Similarity	NPC213197
0.8219	Intermediate Similarity	NPC146540
0.8217	Intermediate Similarity	NPC44452
0.821	Intermediate Similarity	NPC179914
0.8205	Intermediate Similarity	NPC97240
0.8205	Intermediate Similarity	NPC175275
0.8205	Intermediate Similarity	NPC213074
0.8205	Intermediate Similarity	NPC41844
0.8205	Intermediate Similarity	NPC224674
0.8205	Intermediate Similarity	NPC275284
0.8205	Intermediate Similarity	NPC114505
0.8205	Intermediate Similarity	NPC193473
0.8205	Intermediate Similarity	NPC31325
0.8205	Intermediate Similarity	NPC15956
0.8204	Intermediate Similarity	NPC52598
0.82	Intermediate Similarity	NPC472424
0.82	Intermediate Similarity	NPC281241
0.82	Intermediate Similarity	NPC79957
0.82	Intermediate Similarity	NPC86892
0.82	Intermediate Similarity	NPC471625
0.82	Intermediate Similarity	NPC471909
0.82	Intermediate Similarity	NPC33986
0.8194	Intermediate Similarity	NPC163898
0.8188	Intermediate Similarity	NPC318400
0.8188	Intermediate Similarity	NPC296624
0.8188	Intermediate Similarity	NPC207002
0.8188	Intermediate Similarity	NPC133956
0.8188	Intermediate Similarity	NPC167111
0.8188	Intermediate Similarity	NPC471910
0.8182	Intermediate Similarity	NPC469367
0.8182	Intermediate Similarity	NPC152796
0.8182	Intermediate Similarity	NPC475213
0.8182	Intermediate Similarity	NPC204644
0.8182	Intermediate Similarity	NPC478239
0.8182	Intermediate Similarity	NPC178281
0.8182	Intermediate Similarity	NPC186296
0.8176	Intermediate Similarity	NPC254819
0.8171	Intermediate Similarity	NPC326278
0.817	Intermediate Similarity	NPC186406
0.817	Intermediate Similarity	NPC210192
0.817	Intermediate Similarity	NPC46644
0.8165	Intermediate Similarity	NPC98624
0.8165	Intermediate Similarity	NPC183380
0.8158	Intermediate Similarity	NPC100389
0.8158	Intermediate Similarity	NPC183781
0.8155	Intermediate Similarity	NPC471921
0.8155	Intermediate Similarity	NPC129930
0.8155	Intermediate Similarity	NPC474075
0.8155	Intermediate Similarity	NPC471920
0.8155	Intermediate Similarity	NPC471922
0.8155	Intermediate Similarity	NPC292712
0.8155	Intermediate Similarity	NPC114550
0.8155	Intermediate Similarity	NPC312006
0.8155	Intermediate Similarity	NPC20114
0.8153	Intermediate Similarity	NPC472339
0.8153	Intermediate Similarity	NPC270751
0.8151	Intermediate Similarity	NPC473993
0.8146	Intermediate Similarity	NPC471630
0.8146	Intermediate Similarity	NPC476455
0.8146	Intermediate Similarity	NPC177281
0.8146	Intermediate Similarity	NPC128529
0.8146	Intermediate Similarity	NPC55615
0.8146	Intermediate Similarity	NPC475628
0.8146	Intermediate Similarity	NPC283019
0.8146	Intermediate Similarity	NPC160727
0.8146	Intermediate Similarity	NPC149320
0.8144	Intermediate Similarity	NPC191653
0.8141	Intermediate Similarity	NPC474044
0.8133	Intermediate Similarity	NPC260265
0.8133	Intermediate Similarity	NPC326600
0.8133	Intermediate Similarity	NPC267412
0.8133	Intermediate Similarity	NPC166672
0.8133	Intermediate Similarity	NPC253574
0.8133	Intermediate Similarity	NPC47163
0.8133	Intermediate Similarity	NPC98179
0.8133	Intermediate Similarity	NPC100986
0.8133	Intermediate Similarity	NPC198381
0.8133	Intermediate Similarity	NPC50896
0.8133	Intermediate Similarity	NPC74655
0.8133	Intermediate Similarity	NPC195343
0.8133	Intermediate Similarity	NPC84894
0.8133	Intermediate Similarity	NPC319859
0.8133	Intermediate Similarity	NPC287182
0.8133	Intermediate Similarity	NPC164269
0.8133	Intermediate Similarity	NPC127888
0.8133	Intermediate Similarity	NPC18804
0.8133	Intermediate Similarity	NPC204353

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 NPC469699 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	894
0.2-0.3	1650
0.3-0.4	2613
0.4-0.5	2024
0.5-0.6	1086
0.6-0.7	397
0.7-0.8	157
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.817	Intermediate Similarity	NPD6674	Discontinued
0.8158	Intermediate Similarity	NPD5763	Approved
0.8158	Intermediate Similarity	NPD5762	Approved
0.8101	Intermediate Similarity	NPD1653	Approved
0.7892	Intermediate Similarity	NPD7199	Phase 2
0.7881	Intermediate Similarity	NPD4140	Approved
0.7829	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD5124	Phase 1
0.7821	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD8313	Approved
0.7803	Intermediate Similarity	NPD8312	Approved
0.7791	Intermediate Similarity	NPD6559	Discontinued
0.7784	Intermediate Similarity	NPD8127	Discontinued
0.7763	Intermediate Similarity	NPD4060	Phase 1
0.7744	Intermediate Similarity	NPD8455	Phase 2
0.7692	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7266	Discontinued
0.7683	Intermediate Similarity	NPD37	Approved
0.7658	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD5691	Approved
0.7651	Intermediate Similarity	NPD4965	Approved
0.7651	Intermediate Similarity	NPD4967	Phase 2
0.7651	Intermediate Similarity	NPD4966	Approved
0.7619	Intermediate Similarity	NPD1091	Approved
0.7616	Intermediate Similarity	NPD5844	Phase 1
0.7603	Intermediate Similarity	NPD4626	Approved
0.7595	Intermediate Similarity	NPD1652	Phase 2
0.7586	Intermediate Similarity	NPD7685	Pre-registration
0.756	Intermediate Similarity	NPD6234	Discontinued
0.7558	Intermediate Similarity	NPD7228	Approved
0.755	Intermediate Similarity	NPD2861	Phase 2
0.7531	Intermediate Similarity	NPD6273	Approved
0.7516	Intermediate Similarity	NPD7985	Registered
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7097	Phase 1
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5735	Approved
0.7453	Intermediate Similarity	NPD5058	Phase 3
0.7438	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4628	Phase 3
0.7425	Intermediate Similarity	NPD7819	Suspended
0.7421	Intermediate Similarity	NPD2424	Discontinued
0.7416	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7240	Approved
0.7372	Intermediate Similarity	NPD6355	Discontinued
0.7365	Intermediate Similarity	NPD5125	Phase 3
0.7365	Intermediate Similarity	NPD5126	Approved
0.7362	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6004	Phase 3
0.7358	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6005	Phase 3
0.7358	Intermediate Similarity	NPD6002	Phase 3
0.7356	Intermediate Similarity	NPD3818	Discontinued
0.7338	Intermediate Similarity	NPD4625	Phase 3
0.7325	Intermediate Similarity	NPD6653	Approved
0.7314	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3226	Approved
0.7267	Intermediate Similarity	NPD1611	Approved
0.7267	Intermediate Similarity	NPD3705	Approved
0.725	Intermediate Similarity	NPD2346	Discontinued
0.7237	Intermediate Similarity	NPD8651	Approved
0.7233	Intermediate Similarity	NPD7033	Discontinued
0.7219	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7054	Approved
0.7215	Intermediate Similarity	NPD6353	Approved
0.7212	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1613	Approved
0.7197	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7075	Discontinued
0.7188	Intermediate Similarity	NPD2438	Suspended
0.7186	Intermediate Similarity	NPD7458	Discontinued
0.7179	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7472	Approved
0.7175	Intermediate Similarity	NPD7074	Phase 3
0.7171	Intermediate Similarity	NPD4749	Approved
0.7171	Intermediate Similarity	NPD5327	Phase 3
0.7162	Intermediate Similarity	NPD7644	Approved
0.716	Intermediate Similarity	NPD6801	Discontinued
0.7152	Intermediate Similarity	NPD422	Phase 1
0.7151	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD7028	Phase 2
0.7135	Intermediate Similarity	NPD6797	Phase 2
0.7135	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD8032	Phase 2
0.7125	Intermediate Similarity	NPD4108	Discontinued
0.7124	Intermediate Similarity	NPD6696	Suspended
0.7115	Intermediate Similarity	NPD7095	Approved
0.7113	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7783	Phase 2
0.711	Intermediate Similarity	NPD4666	Phase 3
0.7108	Intermediate Similarity	NPD2676	Approved
0.7108	Intermediate Similarity	NPD2675	Approved
0.7105	Intermediate Similarity	NPD7435	Discontinued
0.7095	Intermediate Similarity	NPD7251	Discontinued
0.7091	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3620	Phase 2
0.7089	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3496	Discontinued
0.7078	Intermediate Similarity	NPD2797	Approved
0.707	Intermediate Similarity	NPD6798	Discontinued
0.7063	Intermediate Similarity	NPD4538	Approved
0.7063	Intermediate Similarity	NPD4536	Approved
0.7063	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD3751	Discontinued
0.7056	Intermediate Similarity	NPD7808	Phase 3
0.7055	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD5709	Phase 3
0.7051	Intermediate Similarity	NPD4908	Phase 1
0.7049	Intermediate Similarity	NPD6843	Phase 3
0.7049	Intermediate Similarity	NPD6841	Approved
0.7049	Intermediate Similarity	NPD6842	Approved
0.7048	Intermediate Similarity	NPD2532	Approved
0.7048	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2534	Approved
0.7048	Intermediate Similarity	NPD2533	Approved
0.7037	Intermediate Similarity	NPD6776	Approved
0.7037	Intermediate Similarity	NPD6777	Approved
0.7037	Intermediate Similarity	NPD6779	Approved
0.7037	Intermediate Similarity	NPD6780	Approved
0.7037	Intermediate Similarity	NPD6781	Approved
0.7037	Intermediate Similarity	NPD6778	Approved
0.7037	Intermediate Similarity	NPD6782	Approved
0.7032	Intermediate Similarity	NPD4624	Approved
0.7029	Intermediate Similarity	NPD3787	Discontinued
0.7029	Intermediate Similarity	NPD6232	Discontinued
0.7027	Intermediate Similarity	NPD7157	Approved
0.702	Intermediate Similarity	NPD1778	Approved
0.7019	Intermediate Similarity	NPD5588	Approved
0.7018	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1283	Approved
0.7012	Intermediate Similarity	NPD3750	Approved
0.7012	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4110	Phase 3
0.7006	Intermediate Similarity	NPD7473	Discontinued
0.7	Intermediate Similarity	NPD2157	Approved
0.6981	Remote Similarity	NPD2979	Phase 3
0.6977	Remote Similarity	NPD2415	Discontinued
0.6977	Remote Similarity	NPD3817	Phase 2
0.6977	Remote Similarity	NPD5402	Approved
0.6971	Remote Similarity	NPD6959	Discontinued
0.6968	Remote Similarity	NPD3094	Phase 2
0.6963	Remote Similarity	NPD6823	Phase 2
0.6962	Remote Similarity	NPD3268	Approved
0.6961	Remote Similarity	NPD7549	Discontinued
0.6943	Remote Similarity	NPD7999	Approved
0.6943	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6599	Discontinued
0.6939	Remote Similarity	NPD7843	Approved
0.6937	Remote Similarity	NPD4340	Discontinued
0.6932	Remote Similarity	NPD7229	Phase 3
0.6928	Remote Similarity	NPD6666	Approved
0.6928	Remote Similarity	NPD1610	Phase 2
0.6928	Remote Similarity	NPD6667	Approved
0.6923	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5929	Approved
0.6919	Remote Similarity	NPD1465	Phase 2
0.6918	Remote Similarity	NPD6233	Phase 2
0.6914	Remote Similarity	NPD5494	Approved
0.6914	Remote Similarity	NPD2799	Discontinued
0.6914	Remote Similarity	NPD5960	Phase 3
0.6914	Remote Similarity	NPD3748	Approved
0.6914	Remote Similarity	NPD4308	Phase 3
0.6909	Remote Similarity	NPD7003	Approved
0.6909	Remote Similarity	NPD3892	Phase 2
0.6902	Remote Similarity	NPD8434	Phase 2
0.6901	Remote Similarity	NPD7411	Suspended
0.6899	Remote Similarity	NPD3027	Phase 3
0.6897	Remote Similarity	NPD2684	Approved
0.689	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD7874	Approved
0.6879	Remote Similarity	NPD5736	Approved
0.6879	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7799	Discontinued
0.6871	Remote Similarity	NPD6100	Approved
0.6871	Remote Similarity	NPD2935	Discontinued
0.6871	Remote Similarity	NPD6099	Approved
0.6867	Remote Similarity	NPD2677	Approved
0.6867	Remote Similarity	NPD7340	Approved
0.6864	Remote Similarity	NPD5403	Approved
0.6864	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1934	Approved
0.686	Remote Similarity	NPD4433	Discontinued
0.6859	Remote Similarity	NPD6362	Approved
0.6855	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4481	Phase 3
0.6845	Remote Similarity	NPD5401	Approved
0.6839	Remote Similarity	NPD7698	Approved
0.6839	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7696	Phase 3
0.6839	Remote Similarity	NPD7697	Approved
0.6837	Remote Similarity	NPD8151	Discontinued
0.6834	Remote Similarity	NPD7930	Approved
0.6828	Remote Similarity	NPD290	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