NPASS Compound

Structure

CID202249 OpenBabel06191715592D 26 31 0 0 1 0 0 0 0 0999 V2000 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2395 -0.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8847 0.7471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2971 -1.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 -0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2280 -1.8410 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6141 0.4980 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4223 0.1303 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 3 9 1 0 0 0 0 4 12 2 0 0 0 0 4 15 1 0 0 0 0 5 13 1 0 0 0 0 5 17 2 0 0 0 0 6 14 2 0 0 0 0 6 16 1 0 0 0 0 7 22 1 0 0 0 0 7 23 1 0 0 0 0 8 24 1 0 0 0 0 8 25 1 0 0 0 0 9 1 1 1 0 0 0 9 10 1 0 0 0 0 10 2 1 6 0 0 0 10 18 1 0 0 0 0 11 3 1 1 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 13 21 2 0 0 0 0 14 26 1 0 0 0 0 15 16 2 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 12 1 1 0 0 0 18 19 1 0 0 0 0 19 20 1 1 0 0 0 20 17 1 1 0 0 0 20 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.13
Volume:	342.696
LogP:	3.602
LogD:	3.763
LogS:	-5.041
# Rotatable Bonds:	0
TPSA:	63.22
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.712
Synthetic Accessibility Score:	5.329
Fsp3:	0.55
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:	-4.82
MDCK Permeability:	4.862553396378644e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.055

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.211
Plasma Protein Binding (PPB):	97.69815826416016%
Volume Distribution (VD):	1.207
Pgp-substrate:	2.3436028957366943%

ADMET: Metabolism

CYP1A2-inhibitor:	0.488
CYP1A2-substrate:	0.964
CYP2C19-inhibitor:	0.348
CYP2C19-substrate:	0.867
CYP2C9-inhibitor:	0.41
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.936
CYP3A4-substrate:	0.806

ADMET: Excretion

Clearance (CL):	17.391
Half-life (T1/2):	0.165

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.571
Drug-inuced Liver Injury (DILI):	0.493
AMES Toxicity:	0.134
Rat Oral Acute Toxicity:	0.48
Maximum Recommended Daily Dose:	0.807
Skin Sensitization:	0.642
Carcinogencity:	0.922
Eye Corrosion:	0.004
Eye Irritation:	0.038
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC202249

Natural Product ID:	NPC202249
*Common Name:**	GMTJIWUFFXGFHH-UEHZMWGCSA-N
IUPAC Name:	n.a.
Synonyms:	1'-Epi-Sauchinone
Standard InCHIKey:	GMTJIWUFFXGFHH-UEHZMWGCSA-N
Standard InCHI:	InChI=1S/C20H20O6/c1-9-3-11-13(21)5-17-20(25-8-24-17)19(11)18(10(9)2)12-4-15-16(23-7-22-15)6-14(12)26-20/h4-6,9-11,18-19H,3,7-8H2,1-2H3/t9-,10+,11-,18+,19+,20+/m1/s1
SMILES:	C[C@@H]1C[C@@H]2C(=O)C=C3[C@]4([C@@H]2[C@@H]([C@H]1C)c1cc2c(cc1O4)OCO2)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446987
PubChem CID:	10021151
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924192]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754613]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	root	n.a.	PMID[14750033]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15482936]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	roots	n.a.	n.a.	PMID[18841903]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24359277]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[24387347]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31642320]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20323	Saururus chinensis	Species	Saururaceae	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
AC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	AC50	=	75.9	%	PMID[536890]

☑ 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 NPC202249 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	1674
0.2-0.3	3284
0.3-0.4	8015
0.4-0.5	10576
0.5-0.6	4489
0.6-0.7	7776
0.7-0.8	6214
0.8-0.85	177
0.85-0.9	18
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC188962
1.0	High Similarity	NPC42871
0.8974	High Similarity	NPC220462
0.8854	High Similarity	NPC258644
0.8831	High Similarity	NPC474975
0.8782	High Similarity	NPC273578
0.8766	High Similarity	NPC149505
0.8758	High Similarity	NPC262804
0.8758	High Similarity	NPC40654
0.875	High Similarity	NPC478199
0.871	High Similarity	NPC210642
0.871	High Similarity	NPC13985
0.8693	High Similarity	NPC304687
0.8693	High Similarity	NPC101755
0.8693	High Similarity	NPC80230
0.8693	High Similarity	NPC104024
0.8693	High Similarity	NPC65574
0.8662	High Similarity	NPC244371
0.8645	High Similarity	NPC475170
0.8642	High Similarity	NPC222531
0.8634	High Similarity	NPC469575
0.8627	High Similarity	NPC87295
0.8616	High Similarity	NPC474990
0.8609	High Similarity	NPC80326
0.8606	High Similarity	NPC223375
0.8606	High Similarity	NPC475825
0.8599	High Similarity	NPC292460
0.8581	High Similarity	NPC262455
0.8581	High Similarity	NPC177476
0.8571	High Similarity	NPC115624
0.8562	High Similarity	NPC232883
0.8562	High Similarity	NPC205316
0.8553	High Similarity	NPC155063
0.8544	High Similarity	NPC178195
0.8544	High Similarity	NPC348849
0.8543	High Similarity	NPC300798
0.8543	High Similarity	NPC58137
0.8535	High Similarity	NPC220577
0.8526	High Similarity	NPC177830
0.8519	High Similarity	NPC273021
0.8519	High Similarity	NPC18284
0.8509	High Similarity	NPC119910
0.8509	High Similarity	NPC131557
0.8509	High Similarity	NPC298093
0.8503	High Similarity	NPC66804
0.85	High Similarity	NPC207584
0.85	High Similarity	NPC19947
0.8497	Intermediate Similarity	NPC475000
0.8491	Intermediate Similarity	NPC478238
0.8487	Intermediate Similarity	NPC176586
0.8487	Intermediate Similarity	NPC151423
0.8487	Intermediate Similarity	NPC40237
0.8487	Intermediate Similarity	NPC210354
0.8487	Intermediate Similarity	NPC472562
0.8487	Intermediate Similarity	NPC174522
0.8481	Intermediate Similarity	NPC144162
0.8471	Intermediate Similarity	NPC303519
0.8457	Intermediate Similarity	NPC209411
0.8457	Intermediate Similarity	NPC239890
0.8457	Intermediate Similarity	NPC100465
0.8457	Intermediate Similarity	NPC152424
0.8457	Intermediate Similarity	NPC34376
0.8452	Intermediate Similarity	NPC25496
0.8447	Intermediate Similarity	NPC104459
0.8447	Intermediate Similarity	NPC474043
0.8447	Intermediate Similarity	NPC257914
0.8447	Intermediate Similarity	NPC238405
0.8443	Intermediate Similarity	NPC474568
0.8442	Intermediate Similarity	NPC474158
0.8438	Intermediate Similarity	NPC237946
0.8438	Intermediate Similarity	NPC32373
0.8431	Intermediate Similarity	NPC474288
0.8428	Intermediate Similarity	NPC478213
0.8428	Intermediate Similarity	NPC57211
0.8424	Intermediate Similarity	NPC42230
0.8424	Intermediate Similarity	NPC474948
0.8418	Intermediate Similarity	NPC279061
0.8418	Intermediate Similarity	NPC104353
0.8415	Intermediate Similarity	NPC187923
0.8408	Intermediate Similarity	NPC238366
0.8397	Intermediate Similarity	NPC71726
0.8395	Intermediate Similarity	NPC96593
0.8387	Intermediate Similarity	NPC193779
0.8385	Intermediate Similarity	NPC310206
0.8385	Intermediate Similarity	NPC181168
0.8385	Intermediate Similarity	NPC115281
0.8385	Intermediate Similarity	NPC163527
0.8377	Intermediate Similarity	NPC177644
0.8377	Intermediate Similarity	NPC218841
0.8377	Intermediate Similarity	NPC15743
0.8377	Intermediate Similarity	NPC191158
0.8377	Intermediate Similarity	NPC92693
0.8375	Intermediate Similarity	NPC234730
0.8373	Intermediate Similarity	NPC211309
0.8365	Intermediate Similarity	NPC68882
0.8365	Intermediate Similarity	NPC153008
0.8365	Intermediate Similarity	NPC52623
0.8365	Intermediate Similarity	NPC38469
0.8365	Intermediate Similarity	NPC148497
0.8364	Intermediate Similarity	NPC471923
0.8364	Intermediate Similarity	NPC113093
0.8354	Intermediate Similarity	NPC116759
0.8354	Intermediate Similarity	NPC14294
0.8354	Intermediate Similarity	NPC273959
0.8354	Intermediate Similarity	NPC163002
0.8344	Intermediate Similarity	NPC288149
0.8344	Intermediate Similarity	NPC10304
0.8344	Intermediate Similarity	NPC63256
0.8344	Intermediate Similarity	NPC472567
0.8344	Intermediate Similarity	NPC476058
0.8343	Intermediate Similarity	NPC156635
0.8333	Intermediate Similarity	NPC113055
0.8333	Intermediate Similarity	NPC125713
0.8333	Intermediate Similarity	NPC325122
0.8323	Intermediate Similarity	NPC115123
0.8323	Intermediate Similarity	NPC301897
0.8323	Intermediate Similarity	NPC477380
0.8323	Intermediate Similarity	NPC239113
0.8313	Intermediate Similarity	NPC475453
0.8313	Intermediate Similarity	NPC103197
0.8313	Intermediate Similarity	NPC30009
0.8313	Intermediate Similarity	NPC473531
0.8303	Intermediate Similarity	NPC474647
0.8303	Intermediate Similarity	NPC475953
0.8293	Intermediate Similarity	NPC61141
0.8293	Intermediate Similarity	NPC125991
0.8293	Intermediate Similarity	NPC302741
0.8282	Intermediate Similarity	NPC268718
0.8282	Intermediate Similarity	NPC150943
0.8282	Intermediate Similarity	NPC470637
0.8282	Intermediate Similarity	NPC91634
0.828	Intermediate Similarity	NPC304821
0.8272	Intermediate Similarity	NPC19097
0.8272	Intermediate Similarity	NPC477885
0.8272	Intermediate Similarity	NPC165977
0.8272	Intermediate Similarity	NPC217677
0.8269	Intermediate Similarity	NPC33832
0.8261	Intermediate Similarity	NPC284353
0.8261	Intermediate Similarity	NPC117154
0.8261	Intermediate Similarity	NPC476363
0.8256	Intermediate Similarity	NPC473883
0.8253	Intermediate Similarity	NPC474042
0.8253	Intermediate Similarity	NPC306475
0.8253	Intermediate Similarity	NPC174734
0.8253	Intermediate Similarity	NPC128293
0.8253	Intermediate Similarity	NPC173292
0.825	Intermediate Similarity	NPC166201
0.825	Intermediate Similarity	NPC245948
0.825	Intermediate Similarity	NPC474514
0.8242	Intermediate Similarity	NPC470178
0.8242	Intermediate Similarity	NPC475865
0.8239	Intermediate Similarity	NPC216917
0.8235	Intermediate Similarity	NPC196771
0.8232	Intermediate Similarity	NPC258322
0.8232	Intermediate Similarity	NPC191352
0.8232	Intermediate Similarity	NPC165549
0.8232	Intermediate Similarity	NPC162668
0.8228	Intermediate Similarity	NPC477698
0.8228	Intermediate Similarity	NPC85141
0.8228	Intermediate Similarity	NPC240521
0.8225	Intermediate Similarity	NPC72455
0.8224	Intermediate Similarity	NPC196420
0.8224	Intermediate Similarity	NPC166184
0.8221	Intermediate Similarity	NPC50430
0.8217	Intermediate Similarity	NPC302408
0.8217	Intermediate Similarity	NPC40818
0.8217	Intermediate Similarity	NPC106461
0.8217	Intermediate Similarity	NPC231013
0.8217	Intermediate Similarity	NPC116019
0.8217	Intermediate Similarity	NPC215932
0.8217	Intermediate Similarity	NPC110639
0.8217	Intermediate Similarity	NPC283002
0.8217	Intermediate Similarity	NPC30720
0.8217	Intermediate Similarity	NPC14958
0.8212	Intermediate Similarity	NPC73071
0.821	Intermediate Similarity	NPC261484
0.821	Intermediate Similarity	NPC473900
0.8205	Intermediate Similarity	NPC11422
0.8205	Intermediate Similarity	NPC178014
0.8205	Intermediate Similarity	NPC42716
0.8205	Intermediate Similarity	NPC307466
0.8205	Intermediate Similarity	NPC474749
0.8205	Intermediate Similarity	NPC23955
0.8204	Intermediate Similarity	NPC185498
0.8204	Intermediate Similarity	NPC126204
0.8204	Intermediate Similarity	NPC135345
0.8199	Intermediate Similarity	NPC472408
0.8199	Intermediate Similarity	NPC279930
0.8199	Intermediate Similarity	NPC159922
0.8194	Intermediate Similarity	NPC474966
0.8193	Intermediate Similarity	NPC326520
0.8193	Intermediate Similarity	NPC25361
0.8187	Intermediate Similarity	NPC67302
0.8187	Intermediate Similarity	NPC473732
0.8187	Intermediate Similarity	NPC474663
0.8182	Intermediate Similarity	NPC215612
0.8182	Intermediate Similarity	NPC51681
0.8182	Intermediate Similarity	NPC229632
0.8182	Intermediate Similarity	NPC108767
0.8176	Intermediate Similarity	NPC146803

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 NPC202249 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	392
0.1-0.2	903
0.2-0.3	1766
0.3-0.4	2736
0.4-0.5	1967
0.5-0.6	843
0.6-0.7	461
0.7-0.8	76
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8509	High Similarity	NPD5494	Approved
0.8438	Intermediate Similarity	NPD4966	Approved
0.8438	Intermediate Similarity	NPD4967	Phase 2
0.8438	Intermediate Similarity	NPD4965	Approved
0.8333	Intermediate Similarity	NPD6234	Discontinued
0.825	Intermediate Similarity	NPD37	Approved
0.8204	Intermediate Similarity	NPD7228	Approved
0.8121	Intermediate Similarity	NPD7199	Phase 2
0.805	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7240	Approved
0.7941	Intermediate Similarity	NPD5844	Phase 1
0.7882	Intermediate Similarity	NPD3818	Discontinued
0.7866	Intermediate Similarity	NPD2801	Approved
0.7829	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7074	Phase 3
0.7791	Intermediate Similarity	NPD7028	Phase 2
0.7759	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7054	Approved
0.7697	Intermediate Similarity	NPD1934	Approved
0.7688	Intermediate Similarity	NPD7472	Approved
0.7665	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7473	Discontinued
0.7605	Intermediate Similarity	NPD3817	Phase 2
0.7588	Intermediate Similarity	NPD1247	Approved
0.758	Intermediate Similarity	NPD3748	Approved
0.7562	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD3882	Suspended
0.7557	Intermediate Similarity	NPD7808	Phase 3
0.7545	Intermediate Similarity	NPD1465	Phase 2
0.7544	Intermediate Similarity	NPD6232	Discontinued
0.7543	Intermediate Similarity	NPD6797	Phase 2
0.7532	Intermediate Similarity	NPD6099	Approved
0.7532	Intermediate Similarity	NPD6100	Approved
0.7517	Intermediate Similarity	NPD3705	Approved
0.7515	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7251	Discontinued
0.75	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD6674	Discontinued
0.75	Intermediate Similarity	NPD6559	Discontinued
0.7472	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.7457	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD6166	Phase 2
0.7457	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1653	Approved
0.7442	Intermediate Similarity	NPD3787	Discontinued
0.744	Intermediate Similarity	NPD7819	Suspended
0.7368	Intermediate Similarity	NPD919	Approved
0.7366	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD3750	Approved
0.733	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1511	Approved
0.7312	Intermediate Similarity	NPD2796	Approved
0.7308	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD8127	Discontinued
0.7283	Intermediate Similarity	NPD6959	Discontinued
0.7278	Intermediate Similarity	NPD1933	Approved
0.7273	Intermediate Similarity	NPD2534	Approved
0.7273	Intermediate Similarity	NPD2533	Approved
0.7273	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2532	Approved
0.7247	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7229	Phase 3
0.7235	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD1512	Approved
0.7226	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7680	Approved
0.7197	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5402	Approved
0.7179	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2800	Approved
0.716	Intermediate Similarity	NPD4380	Phase 2
0.716	Intermediate Similarity	NPD6599	Discontinued
0.7158	Intermediate Similarity	NPD5006	Approved
0.7158	Intermediate Similarity	NPD5005	Approved
0.7135	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7411	Suspended
0.7117	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7075	Discontinued
0.711	Intermediate Similarity	NPD3749	Approved
0.7108	Intermediate Similarity	NPD6799	Approved
0.7107	Intermediate Similarity	NPD1613	Approved
0.7107	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3266	Approved
0.7097	Intermediate Similarity	NPD3267	Approved
0.7093	Intermediate Similarity	NPD5353	Approved
0.7089	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD920	Approved
0.7078	Intermediate Similarity	NPD4749	Approved
0.7073	Intermediate Similarity	NPD1243	Approved
0.707	Intermediate Similarity	NPD4908	Phase 1
0.7066	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD2403	Approved
0.7055	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD8032	Phase 2
0.7037	Intermediate Similarity	NPD4420	Approved
0.7035	Intermediate Similarity	NPD8455	Phase 2
0.7033	Intermediate Similarity	NPD8312	Approved
0.7033	Intermediate Similarity	NPD8313	Approved
0.703	Intermediate Similarity	NPD4110	Phase 3
0.703	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7685	Pre-registration
0.7012	Intermediate Similarity	NPD1549	Phase 2
0.7006	Intermediate Similarity	NPD5242	Approved
0.7	Intermediate Similarity	NPD7458	Discontinued
0.6981	Remote Similarity	NPD3268	Approved
0.6981	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7549	Discontinued
0.6977	Remote Similarity	NPD6801	Discontinued
0.6964	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5536	Phase 2
0.6951	Remote Similarity	NPD2346	Discontinued
0.694	Remote Similarity	NPD2968	Approved
0.694	Remote Similarity	NPD2971	Approved
0.6928	Remote Similarity	NPD17	Approved
0.6919	Remote Similarity	NPD8434	Phase 2
0.6919	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3027	Phase 3
0.6918	Remote Similarity	NPD4625	Phase 3
0.6913	Remote Similarity	NPD5283	Phase 1
0.6901	Remote Similarity	NPD3226	Approved
0.6899	Remote Similarity	NPD3018	Phase 2
0.6899	Remote Similarity	NPD2861	Phase 2
0.6895	Remote Similarity	NPD2973	Approved
0.6895	Remote Similarity	NPD2975	Approved
0.6895	Remote Similarity	NPD2974	Approved
0.689	Remote Similarity	NPD2935	Discontinued
0.6886	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2797	Approved
0.6879	Remote Similarity	NPD3384	Approved
0.6879	Remote Similarity	NPD3382	Approved
0.6879	Remote Similarity	NPD3383	Approved
0.6875	Remote Similarity	NPD6778	Approved
0.6875	Remote Similarity	NPD6779	Approved
0.6875	Remote Similarity	NPD6781	Approved
0.6875	Remote Similarity	NPD1296	Phase 2
0.6875	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6776	Approved
0.6875	Remote Similarity	NPD6782	Approved
0.6875	Remote Similarity	NPD6780	Approved
0.6875	Remote Similarity	NPD6777	Approved
0.6875	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4580	Approved
0.6872	Remote Similarity	NPD4481	Phase 3
0.6872	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7097	Phase 1
0.6867	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1651	Approved
0.6857	Remote Similarity	NPD7768	Phase 2
0.6857	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5711	Approved
0.6854	Remote Similarity	NPD5710	Approved
0.6852	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6355	Discontinued
0.6852	Remote Similarity	NPD447	Suspended
0.6852	Remote Similarity	NPD5124	Phase 1
0.6852	Remote Similarity	NPD230	Phase 1
0.6845	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1610	Phase 2
0.6829	Remote Similarity	NPD1510	Phase 2
0.6829	Remote Similarity	NPD2799	Discontinued
0.6826	Remote Similarity	NPD8166	Discontinued
0.6826	Remote Similarity	NPD4628	Phase 3
0.6824	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1607	Approved
0.6807	Remote Similarity	NPD2424	Discontinued
0.6802	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD2981	Phase 2
0.6795	Remote Similarity	NPD1608	Approved
0.6791	Remote Similarity	NPD6842	Approved
0.6791	Remote Similarity	NPD6843	Phase 3
0.6791	Remote Similarity	NPD6841	Approved
0.679	Remote Similarity	NPD1240	Approved
0.679	Remote Similarity	NPD2979	Phase 3
0.6788	Remote Similarity	NPD2438	Suspended
0.6784	Remote Similarity	NPD5403	Approved
0.6769	Remote Similarity	NPD7698	Approved
0.6769	Remote Similarity	NPD7696	Phase 3
0.6769	Remote Similarity	NPD7435	Discontinued
0.6769	Remote Similarity	NPD7697	Approved
0.6768	Remote Similarity	NPD8151	Discontinued
0.6765	Remote Similarity	NPD5401	Approved
0.6753	Remote Similarity	NPD2494	Approved
0.6753	Remote Similarity	NPD5691	Approved
0.6753	Remote Similarity	NPD2493	Approved
0.6752	Remote Similarity	NPD2982	Phase 2
0.6752	Remote Similarity	NPD2983	Phase 2
0.6747	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6002	Phase 3
0.6747	Remote Similarity	NPD7266	Discontinued
0.6747	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6005	Phase 3
0.6747	Remote Similarity	NPD6004	Phase 3

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