NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	460.17
Volume:	450.091
LogP:	2.745
LogD:	2.859
LogS:	-4.1
# Rotatable Bonds:	6
TPSA:	90.91
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.643
Synthetic Accessibility Score:	4.184
Fsp3:	0.458
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:	-4.703
MDCK Permeability:	2.272013807669282e-05
Pgp-inhibitor:	0.479
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	83.68759155273438%
Volume Distribution (VD):	0.762
Pgp-substrate:	6.744787693023682%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.997
CYP2C19-inhibitor:	0.3
CYP2C19-substrate:	0.953
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.167
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.857
CYP3A4-inhibitor:	0.375
CYP3A4-substrate:	0.93

ADMET: Excretion

Clearance (CL):	2.859
Half-life (T1/2):	0.205

ADMET: Toxicity

hERG Blockers:	0.385
Human Hepatotoxicity (H-HT):	0.104
Drug-inuced Liver Injury (DILI):	0.694
AMES Toxicity:	0.114
Rat Oral Acute Toxicity:	0.858
Maximum Recommended Daily Dose:	0.085
Skin Sensitization:	0.363
Carcinogencity:	0.148
Eye Corrosion:	0.003
Eye Irritation:	0.312
Respiratory Toxicity:	0.054

Download Data

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

Natural Product: NPC477960

Natural Product ID:	NPC477960
*Common Name:**	(3R)-4,5,5',6,6',7'-hexamethoxy-7,8'-dimethylspiro[1H-2-benzofuran-3,3'-1H-isochromene]-4'-one
IUPAC Name:	(3R)-4,5,5',6,6',7'-hexamethoxy-7,8'-dimethylspiro[1H-2-benzofuran-3,3'-1H-isochromene]-4'-one
Synonyms:
Standard InCHIKey:	JJQRYVJZLKYSFP-DEOSSOPVSA-N
Standard InCHI:	InChI=1S/C24H28O9/c1-11-13-9-32-24(23(25)15(13)19(28-5)21(30-7)17(11)26-3)16-14(10-33-24)12(2)18(27-4)22(31-8)20(16)29-6/h9-10H2,1-8H3/t24-/m0/s1
SMILES:	CC1=C2CO[C@]3(C4=C(C(=C(C(=C4CO3)C)OC)OC)OC)C(=O)C2=C(C(=C1OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118707790
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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
NPO33576	Spicaria elegans KLA03	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24967847]

☑ 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	3

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50000	nM	PMID[24967847]
NPT2	Others	Unspecified		IC50	>	50000	nM	PMID[24967847]
NPT1453	Organism	Influenza A virus (A/PR/8/34(H1N1))	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50	=	149000	nM	PMID[24967847]

☑ 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 NPC477960 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	468
0.1-0.2	2032
0.2-0.3	4663
0.3-0.4	10875
0.4-0.5	7694
0.5-0.6	4437
0.6-0.7	5956
0.7-0.8	6210
0.8-0.85	347
0.85-0.9	12
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477961
1.0	High Similarity	NPC477962
0.8954	High Similarity	NPC38469
0.8782	High Similarity	NPC155063
0.8782	High Similarity	NPC301897
0.8718	High Similarity	NPC478238
0.8712	High Similarity	NPC471688
0.871	High Similarity	NPC52623
0.8671	High Similarity	NPC238405
0.8671	High Similarity	NPC104459
0.8671	High Similarity	NPC257914
0.8654	High Similarity	NPC57211
0.8654	High Similarity	NPC473664
0.8645	High Similarity	NPC279061
0.8625	High Similarity	NPC302741
0.8608	High Similarity	NPC258644
0.8599	High Similarity	NPC284353
0.858	High Similarity	NPC113093
0.8562	High Similarity	NPC34376
0.8562	High Similarity	NPC65746
0.8535	High Similarity	NPC478213
0.8535	High Similarity	NPC279930
0.8509	High Similarity	NPC273021
0.8509	High Similarity	NPC18284
0.8509	High Similarity	NPC475144
0.8509	High Similarity	NPC125991
0.85	High Similarity	NPC131557
0.8491	Intermediate Similarity	NPC310206
0.8481	Intermediate Similarity	NPC471746
0.8471	Intermediate Similarity	NPC68882
0.8471	Intermediate Similarity	NPC153008
0.8471	Intermediate Similarity	NPC148497
0.8471	Intermediate Similarity	NPC475116
0.8471	Intermediate Similarity	NPC20337
0.8457	Intermediate Similarity	NPC208120
0.8457	Intermediate Similarity	NPC173587
0.8452	Intermediate Similarity	NPC476058
0.8452	Intermediate Similarity	NPC476342
0.8447	Intermediate Similarity	NPC474239
0.8447	Intermediate Similarity	NPC209411
0.8447	Intermediate Similarity	NPC239890
0.8443	Intermediate Similarity	NPC156635
0.8438	Intermediate Similarity	NPC113055
0.8438	Intermediate Similarity	NPC325122
0.8421	Intermediate Similarity	NPC174486
0.8418	Intermediate Similarity	NPC244371
0.8415	Intermediate Similarity	NPC150131
0.8415	Intermediate Similarity	NPC471180
0.8408	Intermediate Similarity	NPC220577
0.8408	Intermediate Similarity	NPC104353
0.8408	Intermediate Similarity	NPC473732
0.8405	Intermediate Similarity	NPC146584
0.8405	Intermediate Similarity	NPC21016
0.8405	Intermediate Similarity	NPC326520
0.8397	Intermediate Similarity	NPC181250
0.8395	Intermediate Similarity	NPC61141
0.8395	Intermediate Similarity	NPC478199
0.8395	Intermediate Similarity	NPC469575
0.8395	Intermediate Similarity	NPC474763
0.8393	Intermediate Similarity	NPC67302
0.8387	Intermediate Similarity	NPC117463
0.8385	Intermediate Similarity	NPC475886
0.8385	Intermediate Similarity	NPC298093
0.8385	Intermediate Similarity	NPC474287
0.8383	Intermediate Similarity	NPC108202
0.8383	Intermediate Similarity	NPC146803
0.8377	Intermediate Similarity	NPC224687
0.8377	Intermediate Similarity	NPC296575
0.8375	Intermediate Similarity	NPC217677
0.8375	Intermediate Similarity	NPC165977
0.8373	Intermediate Similarity	NPC475825
0.8373	Intermediate Similarity	NPC223375
0.8366	Intermediate Similarity	NPC476054
0.8364	Intermediate Similarity	NPC242395
0.8354	Intermediate Similarity	NPC170245
0.8354	Intermediate Similarity	NPC292460
0.8344	Intermediate Similarity	NPC474350
0.8344	Intermediate Similarity	NPC216917
0.8344	Intermediate Similarity	NPC259058
0.8344	Intermediate Similarity	NPC201547
0.8344	Intermediate Similarity	NPC474240
0.8344	Intermediate Similarity	NPC41301
0.8343	Intermediate Similarity	NPC244903
0.8333	Intermediate Similarity	NPC474186
0.8333	Intermediate Similarity	NPC474351
0.8333	Intermediate Similarity	NPC475883
0.8333	Intermediate Similarity	NPC474187
0.8323	Intermediate Similarity	NPC470336
0.8323	Intermediate Similarity	NPC474568
0.8323	Intermediate Similarity	NPC474043
0.8323	Intermediate Similarity	NPC310259
0.8323	Intermediate Similarity	NPC470335
0.8323	Intermediate Similarity	NPC62640
0.8323	Intermediate Similarity	NPC315157
0.8323	Intermediate Similarity	NPC125713
0.8313	Intermediate Similarity	NPC72249
0.8312	Intermediate Similarity	NPC182842
0.8312	Intermediate Similarity	NPC27106
0.8303	Intermediate Similarity	NPC76482
0.8303	Intermediate Similarity	NPC232936
0.8293	Intermediate Similarity	NPC187923
0.8293	Intermediate Similarity	NPC475888
0.8293	Intermediate Similarity	NPC327652
0.8291	Intermediate Similarity	NPC474170
0.8291	Intermediate Similarity	NPC474388
0.8291	Intermediate Similarity	NPC472535
0.8291	Intermediate Similarity	NPC474414
0.8286	Intermediate Similarity	NPC314020
0.8284	Intermediate Similarity	NPC168584
0.8282	Intermediate Similarity	NPC108767
0.8282	Intermediate Similarity	NPC211107
0.8282	Intermediate Similarity	NPC215612
0.828	Intermediate Similarity	NPC69752
0.828	Intermediate Similarity	NPC238366
0.8272	Intermediate Similarity	NPC78944
0.8272	Intermediate Similarity	NPC36217
0.8272	Intermediate Similarity	NPC56085
0.8272	Intermediate Similarity	NPC299436
0.8272	Intermediate Similarity	NPC470358
0.8272	Intermediate Similarity	NPC65784
0.8272	Intermediate Similarity	NPC14353
0.8272	Intermediate Similarity	NPC470326
0.8272	Intermediate Similarity	NPC269906
0.8272	Intermediate Similarity	NPC228785
0.8269	Intermediate Similarity	NPC474999
0.8269	Intermediate Similarity	NPC299923
0.8269	Intermediate Similarity	NPC470511
0.8263	Intermediate Similarity	NPC121333
0.8263	Intermediate Similarity	NPC471181
0.8261	Intermediate Similarity	NPC19097
0.8261	Intermediate Similarity	NPC167595
0.8258	Intermediate Similarity	NPC87295
0.8258	Intermediate Similarity	NPC165512
0.8253	Intermediate Similarity	NPC213416
0.8253	Intermediate Similarity	NPC152477
0.8253	Intermediate Similarity	NPC473202
0.8253	Intermediate Similarity	NPC476771
0.825	Intermediate Similarity	NPC276059
0.825	Intermediate Similarity	NPC122623
0.825	Intermediate Similarity	NPC34725
0.825	Intermediate Similarity	NPC241774
0.825	Intermediate Similarity	NPC16286
0.8242	Intermediate Similarity	NPC475214
0.8242	Intermediate Similarity	NPC472895
0.8242	Intermediate Similarity	NPC472452
0.8242	Intermediate Similarity	NPC298071
0.8242	Intermediate Similarity	NPC477517
0.8242	Intermediate Similarity	NPC329119
0.8239	Intermediate Similarity	NPC40033
0.8239	Intermediate Similarity	NPC166201
0.8235	Intermediate Similarity	NPC212290
0.8232	Intermediate Similarity	NPC197168
0.8232	Intermediate Similarity	NPC18100
0.8232	Intermediate Similarity	NPC273959
0.8232	Intermediate Similarity	NPC205265
0.8232	Intermediate Similarity	NPC472281
0.8232	Intermediate Similarity	NPC470459
0.8232	Intermediate Similarity	NPC7483
0.8232	Intermediate Similarity	NPC475985
0.8228	Intermediate Similarity	NPC29056
0.8228	Intermediate Similarity	NPC234152
0.8228	Intermediate Similarity	NPC477676
0.8228	Intermediate Similarity	NPC177839
0.8221	Intermediate Similarity	NPC94155
0.8221	Intermediate Similarity	NPC278052
0.8221	Intermediate Similarity	NPC471499
0.8221	Intermediate Similarity	NPC474779
0.8221	Intermediate Similarity	NPC40491
0.8221	Intermediate Similarity	NPC61010
0.8217	Intermediate Similarity	NPC63256
0.8217	Intermediate Similarity	NPC183236
0.8217	Intermediate Similarity	NPC10304
0.821	Intermediate Similarity	NPC215375
0.821	Intermediate Similarity	NPC250076
0.821	Intermediate Similarity	NPC62518
0.821	Intermediate Similarity	NPC100123
0.8205	Intermediate Similarity	NPC283002
0.8205	Intermediate Similarity	NPC120924
0.8205	Intermediate Similarity	NPC302408
0.8205	Intermediate Similarity	NPC195919
0.8205	Intermediate Similarity	NPC216314
0.8204	Intermediate Similarity	NPC212748
0.8204	Intermediate Similarity	NPC477670
0.8204	Intermediate Similarity	NPC279209
0.8204	Intermediate Similarity	NPC102277
0.8199	Intermediate Similarity	NPC474983
0.8199	Intermediate Similarity	NPC303255
0.8199	Intermediate Similarity	NPC257277
0.8199	Intermediate Similarity	NPC477380
0.8199	Intermediate Similarity	NPC150227
0.8194	Intermediate Similarity	NPC293201
0.8194	Intermediate Similarity	NPC470932
0.8193	Intermediate Similarity	NPC149244
0.8193	Intermediate Similarity	NPC265530
0.8193	Intermediate Similarity	NPC477502
0.8193	Intermediate Similarity	NPC226304
0.8193	Intermediate Similarity	NPC48640
0.8193	Intermediate Similarity	NPC325555
0.8193	Intermediate Similarity	NPC42892
0.8193	Intermediate Similarity	NPC474948

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 NPC477960 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	398
0.1-0.2	1113
0.2-0.3	2257
0.3-0.4	2743
0.4-0.5	1591
0.5-0.6	710
0.6-0.7	243
0.7-0.8	92
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8385	Intermediate Similarity	NPD5494	Approved
0.825	Intermediate Similarity	NPD3817	Phase 2
0.8086	Intermediate Similarity	NPD3882	Suspended
0.8084	Intermediate Similarity	NPD3818	Discontinued
0.8061	Intermediate Similarity	NPD6232	Discontinued
0.8038	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD2532	Approved
0.8025	Intermediate Similarity	NPD2534	Approved
0.8025	Intermediate Similarity	NPD2533	Approved
0.8024	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD1247	Approved
0.7988	Intermediate Similarity	NPD919	Approved
0.7963	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD7819	Suspended
0.7953	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD7808	Phase 3
0.7941	Intermediate Similarity	NPD6797	Phase 2
0.7904	Intermediate Similarity	NPD3926	Phase 2
0.7901	Intermediate Similarity	NPD1934	Approved
0.7895	Intermediate Similarity	NPD7251	Discontinued
0.7882	Intermediate Similarity	NPD7074	Phase 3
0.7857	Intermediate Similarity	NPD6166	Phase 2
0.7857	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7054	Approved
0.7818	Intermediate Similarity	NPD7075	Discontinued
0.7798	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6801	Discontinued
0.7791	Intermediate Similarity	NPD37	Approved
0.7778	Intermediate Similarity	NPD7472	Approved
0.7758	Intermediate Similarity	NPD4965	Approved
0.7758	Intermediate Similarity	NPD4967	Phase 2
0.7758	Intermediate Similarity	NPD4966	Approved
0.7744	Intermediate Similarity	NPD2801	Approved
0.7688	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6959	Discontinued
0.7669	Intermediate Similarity	NPD4380	Phase 2
0.7665	Intermediate Similarity	NPD6234	Discontinued
0.7625	Intermediate Similarity	NPD6799	Approved
0.7616	Intermediate Similarity	NPD5844	Phase 1
0.7605	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2800	Approved
0.7586	Intermediate Similarity	NPD6559	Discontinued
0.7574	Intermediate Similarity	NPD7199	Phase 2
0.7561	Intermediate Similarity	NPD6599	Discontinued
0.7545	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1512	Approved
0.753	Intermediate Similarity	NPD1465	Phase 2
0.7529	Intermediate Similarity	NPD5711	Approved
0.7529	Intermediate Similarity	NPD5710	Approved
0.7516	Intermediate Similarity	NPD2796	Approved
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD920	Approved
0.7457	Intermediate Similarity	NPD7228	Approved
0.7436	Intermediate Similarity	NPD6651	Approved
0.7427	Intermediate Similarity	NPD3787	Discontinued
0.741	Intermediate Similarity	NPD7411	Suspended
0.7407	Intermediate Similarity	NPD1511	Approved
0.7389	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5402	Approved
0.7381	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3751	Discontinued
0.7353	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7240	Approved
0.7267	Intermediate Similarity	NPD1243	Approved
0.7261	Intermediate Similarity	NPD1933	Approved
0.7256	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2403	Approved
0.7234	Intermediate Similarity	NPD5005	Approved
0.7234	Intermediate Similarity	NPD5006	Approved
0.7233	Intermediate Similarity	NPD1510	Phase 2
0.7219	Intermediate Similarity	NPD6777	Approved
0.7219	Intermediate Similarity	NPD6780	Approved
0.7219	Intermediate Similarity	NPD6776	Approved
0.7219	Intermediate Similarity	NPD6781	Approved
0.7219	Intermediate Similarity	NPD6779	Approved
0.7219	Intermediate Similarity	NPD6782	Approved
0.7219	Intermediate Similarity	NPD6778	Approved
0.7205	Intermediate Similarity	NPD1549	Phase 2
0.7196	Intermediate Similarity	NPD7435	Discontinued
0.7193	Intermediate Similarity	NPD3749	Approved
0.7169	Intermediate Similarity	NPD5403	Approved
0.7152	Intermediate Similarity	NPD5401	Approved
0.7143	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2346	Discontinued
0.7134	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3748	Approved
0.7112	Intermediate Similarity	NPD4420	Approved
0.7105	Intermediate Similarity	NPD7696	Phase 3
0.7105	Intermediate Similarity	NPD7698	Approved
0.7105	Intermediate Similarity	NPD7697	Approved
0.7098	Intermediate Similarity	NPD8151	Discontinued
0.7089	Intermediate Similarity	NPD1240	Approved
0.7086	Intermediate Similarity	NPD5242	Approved
0.7083	Intermediate Similarity	NPD3226	Approved
0.7068	Intermediate Similarity	NPD7871	Phase 2
0.7068	Intermediate Similarity	NPD7870	Phase 2
0.7043	Intermediate Similarity	NPD6535	Approved
0.7043	Intermediate Similarity	NPD6534	Approved
0.7039	Intermediate Similarity	NPD3705	Approved
0.7037	Intermediate Similarity	NPD1471	Phase 3
0.7019	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD8313	Approved
0.7017	Intermediate Similarity	NPD8312	Approved
0.7	Intermediate Similarity	NPD1607	Approved
0.6988	Remote Similarity	NPD7390	Discontinued
0.6977	Remote Similarity	NPD5353	Approved
0.6975	Remote Similarity	NPD2935	Discontinued
0.6974	Remote Similarity	NPD7874	Approved
0.6974	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7701	Phase 2
0.6951	Remote Similarity	NPD6674	Discontinued
0.6936	Remote Similarity	NPD7768	Phase 2
0.6932	Remote Similarity	NPD7229	Phase 3
0.6931	Remote Similarity	NPD7700	Phase 2
0.6931	Remote Similarity	NPD7699	Phase 2
0.6914	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3750	Approved
0.6906	Remote Similarity	NPD7685	Pre-registration
0.6902	Remote Similarity	NPD8434	Phase 2
0.6902	Remote Similarity	NPD8150	Discontinued
0.6875	Remote Similarity	NPD943	Approved
0.6853	Remote Similarity	NPD7801	Approved
0.6848	Remote Similarity	NPD2654	Approved
0.6848	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD230	Phase 1
0.6815	Remote Similarity	NPD2798	Approved
0.681	Remote Similarity	NPD2799	Discontinued
0.6804	Remote Similarity	NPD8320	Phase 1
0.6804	Remote Similarity	NPD8319	Approved
0.6802	Remote Similarity	NPD6386	Approved
0.6802	Remote Similarity	NPD6385	Approved
0.6793	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6823	Phase 2
0.6784	Remote Similarity	NPD7458	Discontinued
0.6776	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6190	Approved
0.6758	Remote Similarity	NPD5953	Discontinued
0.675	Remote Similarity	NPD2313	Discontinued
0.675	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.674	Remote Similarity	NPD7286	Phase 2
0.673	Remote Similarity	NPD6832	Phase 2
0.6728	Remote Similarity	NPD447	Suspended
0.6719	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD8366	Approved
0.6686	Remote Similarity	NPD5978	Approved
0.6686	Remote Similarity	NPD5977	Approved
0.6684	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7783	Phase 2
0.6683	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2438	Suspended
0.6667	Remote Similarity	NPD6100	Approved
0.6647	Remote Similarity	NPD7028	Phase 2
0.6634	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6213	Phase 3
0.6632	Remote Similarity	NPD6212	Phase 3
0.6632	Remote Similarity	NPD8285	Discontinued
0.6632	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD8455	Phase 2
0.6628	Remote Similarity	NPD1653	Approved
0.6627	Remote Similarity	NPD2344	Approved
0.6626	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD2974	Approved
0.6615	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD2975	Approved
0.6615	Remote Similarity	NPD2973	Approved
0.6607	Remote Similarity	NPD4628	Phase 3
0.6603	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD8491	Approved
0.6584	Remote Similarity	NPD7930	Approved
0.6584	Remote Similarity	NPD3027	Phase 3
0.6582	Remote Similarity	NPD7680	Approved
0.6566	Remote Similarity	NPD1551	Phase 2
0.6566	Remote Similarity	NPD7584	Approved
0.6564	Remote Similarity	NPD2979	Phase 3
0.6564	Remote Similarity	NPD1613	Approved
0.6564	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD4060	Phase 1
0.6562	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3018	Phase 2
0.6559	Remote Similarity	NPD2971	Approved
0.6559	Remote Similarity	NPD2968	Approved
0.6554	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD2343	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data