NPASS Compound

Structure

NPC179250 OpenBabel07101719152D 45 49 0 0 1 0 0 0 0 0999 V2000 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 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 -2.5981 1.5000 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 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 -1.7321 0.0000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 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 -2.5981 -0.5000 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 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 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 -5.1962 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 43 1 0 0 0 0 2 8 1 0 0 0 0 2 22 2 0 0 0 0 3 9 2 0 0 0 0 3 22 1 0 0 0 0 4 10 1 0 0 0 0 4 23 2 0 0 0 0 5 11 2 0 0 0 0 5 23 1 0 0 0 0 6 12 2 0 0 0 0 6 24 1 0 0 0 0 7 13 2 0 0 0 0 7 24 1 0 0 0 0 8 26 2 0 0 0 0 9 26 1 0 0 0 0 10 27 2 0 0 0 0 11 27 1 0 0 0 0 12 30 1 0 0 0 0 13 32 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 36 1 0 0 0 0 17 37 1 0 0 0 0 18 24 2 0 0 0 0 18 31 1 0 0 0 0 19 25 2 0 0 0 0 19 28 1 0 0 0 0 20 25 1 0 0 0 0 20 29 2 0 0 0 0 21 28 2 0 0 0 0 21 29 1 0 0 0 0 26 38 1 0 0 0 0 27 39 1 0 0 0 0 28 40 1 0 0 0 0 29 43 1 0 0 0 0 30 31 2 0 0 0 0 30 44 1 0 0 0 0 31 45 1 0 0 0 0 32 36 2 3 0 0 0 32 41 1 0 0 0 0 33 25 1 1 0 0 0 33 34 1 0 0 0 0 33 44 1 0 0 0 0 34 35 1 6 0 0 0 34 45 1 0 0 0 0 35 37 2 3 0 0 0 35 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	610.23
Volume:	623.902
LogP:	4.015
LogD:	3.661
LogS:	-4.476
# Rotatable Bonds:	13
TPSA:	146.58
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.157
Synthetic Accessibility Score:	3.593
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.75
MDCK Permeability:	5.3719991228717845e-06
Pgp-inhibitor:	0.469
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.745
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	99.00801849365234%
Volume Distribution (VD):	0.627
Pgp-substrate:	0.6510718464851379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.441
CYP1A2-substrate:	0.186
CYP2C19-inhibitor:	0.94
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.942
CYP2C9-substrate:	0.759
CYP2D6-inhibitor:	0.918
CYP2D6-substrate:	0.514
CYP3A4-inhibitor:	0.951
CYP3A4-substrate:	0.33

ADMET: Excretion

Clearance (CL):	7.93
Half-life (T1/2):	0.722

ADMET: Toxicity

hERG Blockers:	0.624
Human Hepatotoxicity (H-HT):	0.573
Drug-inuced Liver Injury (DILI):	0.384
AMES Toxicity:	0.434
Rat Oral Acute Toxicity:	0.257
Maximum Recommended Daily Dose:	0.826
Skin Sensitization:	0.556
Carcinogencity:	0.101
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.009

Download Data

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

Natural Product: NPC179250

Natural Product ID:	NPC179250
*Common Name:**	(2R,3S)-2-(3-Hydroxy-5-Methoxyphenyl)-N-[2-(4-Hydroxyphenyl)Ethyl]-6-[(Z)-3-[2-(4-Hydroxyphenyl)Ethylamino]-3-Oxoprop-1-Enyl]-2,3-Dihydro-1,4-Benzodioxine-3-Carboxamide
IUPAC Name:	(2R,3S)-2-(3-hydroxy-5-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-6-[(Z)-3-[2-(4-hydroxyphenyl)ethylamino]-3-oxoprop-1-enyl]-2,3-dihydro-1,4-benzodioxine-3-carboxamide
Synonyms:
Standard InCHIKey:	ABUYVRIWKJMSGL-HYKZEENLSA-N
Standard InCHI:	InChI=1S/C35H34N2O8/c1-43-29-20-25(19-28(40)21-29)33-34(35(42)37-17-15-23-4-10-27(39)11-5-23)45-31-18-24(6-12-30(31)44-33)7-13-32(41)36-16-14-22-2-8-26(38)9-3-22/h2-13,18-21,33-34,38-40H,14-17H2,1H3,(H,36,41)(H,37,42)/b13-7-/t33-,34+/m1/s1
SMILES:	COc1cc(cc(c1)O)[C@@H]1[C@@H](C(=NCCc2ccc(cc2)O)O)Oc2cc(ccc2O1)/C=CC(=NCCc1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337121
PubChem CID:	71521887
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002699] Benzodioxanes [CHEMONTID:0002704] Phenylbenzodioxanes [CHEMONTID:0002707] Phenylbenzo-1,4-dioxanes

*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
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[12467621]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	root	n.a.	PMID[16212233]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	root bark	n.a.	n.a.	PMID[23282106]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[26982999]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[9090870]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17823	Lycium chinense	Species	Solanaceae	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

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	44100.0	nM	PMID[559009]
NPT1	Others	Radical scavenging activity		IC50	=	48200.0	nM	PMID[559009]

☑ 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 NPC179250 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	268
0.1-0.2	1451
0.2-0.3	6595
0.3-0.4	12019
0.4-0.5	4692
0.5-0.6	7238
0.6-0.7	8035
0.7-0.8	2270
0.8-0.85	113
0.85-0.9	10
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC50380
0.9156	High Similarity	NPC107602
0.9013	High Similarity	NPC470935
0.9013	High Similarity	NPC471032
0.8961	High Similarity	NPC127402
0.8938	High Similarity	NPC90984
0.8742	High Similarity	NPC222039
0.8742	High Similarity	NPC100478
0.8581	High Similarity	NPC277857
0.8581	High Similarity	NPC115144
0.8571	High Similarity	NPC5462
0.8553	High Similarity	NPC262189
0.8543	High Similarity	NPC296898
0.8471	Intermediate Similarity	NPC281549
0.8365	Intermediate Similarity	NPC477612
0.8333	Intermediate Similarity	NPC171932
0.8333	Intermediate Similarity	NPC28440
0.8312	Intermediate Similarity	NPC22317
0.8303	Intermediate Similarity	NPC470936
0.8302	Intermediate Similarity	NPC321657
0.8302	Intermediate Similarity	NPC318373
0.8301	Intermediate Similarity	NPC474390
0.8301	Intermediate Similarity	NPC299583
0.8286	Intermediate Similarity	NPC41122
0.8286	Intermediate Similarity	NPC318805
0.8235	Intermediate Similarity	NPC312770
0.8235	Intermediate Similarity	NPC204848
0.8235	Intermediate Similarity	NPC41473
0.8235	Intermediate Similarity	NPC14600
0.8235	Intermediate Similarity	NPC160607
0.8224	Intermediate Similarity	NPC170694
0.8202	Intermediate Similarity	NPC234318
0.8194	Intermediate Similarity	NPC266197
0.8194	Intermediate Similarity	NPC291101
0.8187	Intermediate Similarity	NPC211561
0.8187	Intermediate Similarity	NPC475250
0.8187	Intermediate Similarity	NPC470826
0.8187	Intermediate Similarity	NPC476969
0.8187	Intermediate Similarity	NPC470098
0.8187	Intermediate Similarity	NPC473266
0.8146	Intermediate Similarity	NPC469625
0.8146	Intermediate Similarity	NPC469613
0.8146	Intermediate Similarity	NPC30043
0.8129	Intermediate Similarity	NPC22517
0.8125	Intermediate Similarity	NPC139699
0.8125	Intermediate Similarity	NPC114659
0.8092	Intermediate Similarity	NPC7903
0.8092	Intermediate Similarity	NPC16208
0.8092	Intermediate Similarity	NPC35932
0.8092	Intermediate Similarity	NPC184447
0.8092	Intermediate Similarity	NPC160991
0.8092	Intermediate Similarity	NPC474134
0.8092	Intermediate Similarity	NPC131128
0.809	Intermediate Similarity	NPC85381
0.8086	Intermediate Similarity	NPC324517
0.8086	Intermediate Similarity	NPC329343
0.8086	Intermediate Similarity	NPC321972
0.8079	Intermediate Similarity	NPC114102
0.8079	Intermediate Similarity	NPC469614
0.8079	Intermediate Similarity	NPC469612
0.8065	Intermediate Similarity	NPC211549
0.8063	Intermediate Similarity	NPC236202
0.8063	Intermediate Similarity	NPC204770
0.8063	Intermediate Similarity	NPC70409
0.8063	Intermediate Similarity	NPC18185
0.8063	Intermediate Similarity	NPC170103
0.8063	Intermediate Similarity	NPC58190
0.8063	Intermediate Similarity	NPC108811
0.8063	Intermediate Similarity	NPC262911
0.8063	Intermediate Similarity	NPC202742
0.8063	Intermediate Similarity	NPC82917
0.8063	Intermediate Similarity	NPC263940
0.8063	Intermediate Similarity	NPC294558
0.8052	Intermediate Similarity	NPC112939
0.8052	Intermediate Similarity	NPC470356
0.8052	Intermediate Similarity	NPC474206
0.8052	Intermediate Similarity	NPC112246
0.8052	Intermediate Similarity	NPC121812
0.8052	Intermediate Similarity	NPC61946
0.8052	Intermediate Similarity	NPC94750
0.8046	Intermediate Similarity	NPC30779
0.8037	Intermediate Similarity	NPC279406
0.8037	Intermediate Similarity	NPC226809
0.8026	Intermediate Similarity	NPC470095
0.8026	Intermediate Similarity	NPC470096
0.8026	Intermediate Similarity	NPC214869
0.8026	Intermediate Similarity	NPC472597
0.8025	Intermediate Similarity	NPC178054
0.8025	Intermediate Similarity	NPC470372
0.8013	Intermediate Similarity	NPC273295
0.8013	Intermediate Similarity	NPC35961
0.8013	Intermediate Similarity	NPC202582
0.8013	Intermediate Similarity	NPC52029
0.8013	Intermediate Similarity	NPC55947
0.8013	Intermediate Similarity	NPC226788
0.8013	Intermediate Similarity	NPC218856
0.8013	Intermediate Similarity	NPC470258
0.8013	Intermediate Similarity	NPC210623
0.8013	Intermediate Similarity	NPC260842
0.8013	Intermediate Similarity	NPC3439
0.8013	Intermediate Similarity	NPC190629
0.8013	Intermediate Similarity	NPC195749
0.8013	Intermediate Similarity	NPC222004
0.8013	Intermediate Similarity	NPC285339
0.8012	Intermediate Similarity	NPC182119
0.8012	Intermediate Similarity	NPC20757
0.8012	Intermediate Similarity	NPC227516
0.8	Intermediate Similarity	NPC306441
0.8	Intermediate Similarity	NPC96576
0.8	Intermediate Similarity	NPC474639
0.8	Intermediate Similarity	NPC16435
0.8	Intermediate Similarity	NPC230734
0.8	Intermediate Similarity	NPC227503
0.7989	Intermediate Similarity	NPC286119
0.7989	Intermediate Similarity	NPC195538
0.7988	Intermediate Similarity	NPC224161
0.7987	Intermediate Similarity	NPC310854
0.7987	Intermediate Similarity	NPC66840
0.7987	Intermediate Similarity	NPC470097
0.7987	Intermediate Similarity	NPC256307
0.7987	Intermediate Similarity	NPC471415
0.7987	Intermediate Similarity	NPC114119
0.7975	Intermediate Similarity	NPC469559
0.7974	Intermediate Similarity	NPC201587
0.7974	Intermediate Similarity	NPC253105
0.7974	Intermediate Similarity	NPC470752
0.7962	Intermediate Similarity	NPC472091
0.7962	Intermediate Similarity	NPC472092
0.7962	Intermediate Similarity	NPC472090
0.7961	Intermediate Similarity	NPC472338
0.795	Intermediate Similarity	NPC327412
0.795	Intermediate Similarity	NPC328567
0.795	Intermediate Similarity	NPC320970
0.795	Intermediate Similarity	NPC320671
0.7949	Intermediate Similarity	NPC102904
0.7949	Intermediate Similarity	NPC176051
0.7949	Intermediate Similarity	NPC103976
0.7949	Intermediate Similarity	NPC474282
0.7949	Intermediate Similarity	NPC326797
0.7949	Intermediate Similarity	NPC107551
0.7947	Intermediate Similarity	NPC155838
0.7943	Intermediate Similarity	NPC251735
0.7943	Intermediate Similarity	NPC285931
0.7943	Intermediate Similarity	NPC328155
0.7943	Intermediate Similarity	NPC181796
0.7943	Intermediate Similarity	NPC271013
0.7943	Intermediate Similarity	NPC8836
0.7943	Intermediate Similarity	NPC217748
0.7943	Intermediate Similarity	NPC54654
0.7943	Intermediate Similarity	NPC290582
0.7943	Intermediate Similarity	NPC7715
0.7943	Intermediate Similarity	NPC279228
0.7943	Intermediate Similarity	NPC104196
0.7943	Intermediate Similarity	NPC42663
0.7943	Intermediate Similarity	NPC222661
0.7943	Intermediate Similarity	NPC239824
0.7943	Intermediate Similarity	NPC15414
0.7943	Intermediate Similarity	NPC49075
0.7943	Intermediate Similarity	NPC182052
0.7943	Intermediate Similarity	NPC258657
0.7943	Intermediate Similarity	NPC229373
0.7943	Intermediate Similarity	NPC311973
0.7943	Intermediate Similarity	NPC90998
0.7943	Intermediate Similarity	NPC290005
0.7943	Intermediate Similarity	NPC476202
0.7943	Intermediate Similarity	NPC185639
0.7943	Intermediate Similarity	NPC223690
0.7939	Intermediate Similarity	NPC46335
0.7939	Intermediate Similarity	NPC157333
0.7937	Intermediate Similarity	NPC274960
0.7937	Intermediate Similarity	NPC143120
0.7937	Intermediate Similarity	NPC473909
0.7937	Intermediate Similarity	NPC181615
0.7935	Intermediate Similarity	NPC260898
0.7935	Intermediate Similarity	NPC151224
0.7935	Intermediate Similarity	NPC234333
0.7935	Intermediate Similarity	NPC47398
0.7927	Intermediate Similarity	NPC187028
0.7927	Intermediate Similarity	NPC18249
0.7927	Intermediate Similarity	NPC10221
0.7927	Intermediate Similarity	NPC140915
0.7927	Intermediate Similarity	NPC197741
0.7927	Intermediate Similarity	NPC305700
0.7922	Intermediate Similarity	NPC11060
0.7922	Intermediate Similarity	NPC168059
0.7922	Intermediate Similarity	NPC263064
0.7922	Intermediate Similarity	NPC229442
0.7914	Intermediate Similarity	NPC474560
0.791	Intermediate Similarity	NPC212237
0.791	Intermediate Similarity	NPC116465
0.7908	Intermediate Similarity	NPC309787
0.7908	Intermediate Similarity	NPC474238
0.7898	Intermediate Similarity	NPC49172
0.7898	Intermediate Similarity	NPC274716
0.7898	Intermediate Similarity	NPC254441
0.7898	Intermediate Similarity	NPC167116
0.7895	Intermediate Similarity	NPC86030
0.7895	Intermediate Similarity	NPC5851
0.7888	Intermediate Similarity	NPC260397
0.7888	Intermediate Similarity	NPC324492

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 NPC179250 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	716
0.2-0.3	1234
0.3-0.4	2547
0.4-0.5	2262
0.5-0.6	1406
0.6-0.7	716
0.7-0.8	97
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8313	Intermediate Similarity	NPD4675	Approved
0.8313	Intermediate Similarity	NPD4678	Approved
0.8121	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4123	Phase 3
0.7943	Intermediate Similarity	NPD8053	Approved
0.7943	Intermediate Similarity	NPD8054	Approved
0.7831	Intermediate Similarity	NPD5773	Approved
0.7831	Intermediate Similarity	NPD5772	Approved
0.7805	Intermediate Similarity	NPD4005	Discontinued
0.7778	Intermediate Similarity	NPD7447	Phase 1
0.7778	Intermediate Similarity	NPD3027	Phase 3
0.7771	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6331	Phase 2
0.775	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1613	Approved
0.7716	Intermediate Similarity	NPD7212	Phase 2
0.7716	Intermediate Similarity	NPD7213	Phase 3
0.7701	Intermediate Similarity	NPD8156	Discontinued
0.7683	Intermediate Similarity	NPD2122	Discontinued
0.7644	Intermediate Similarity	NPD8251	Approved
0.7644	Intermediate Similarity	NPD8252	Approved
0.7644	Intermediate Similarity	NPD8099	Discontinued
0.7628	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD2674	Phase 3
0.7532	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7153	Discontinued
0.7515	Intermediate Similarity	NPD7526	Approved
0.7515	Intermediate Similarity	NPD52	Approved
0.7515	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2161	Phase 2
0.7485	Intermediate Similarity	NPD2219	Phase 1
0.7484	Intermediate Similarity	NPD4908	Phase 1
0.743	Intermediate Similarity	NPD7549	Discontinued
0.7405	Intermediate Similarity	NPD1558	Phase 1
0.7396	Intermediate Similarity	NPD6072	Discontinued
0.7394	Intermediate Similarity	NPD4357	Discontinued
0.7389	Intermediate Similarity	NPD3144	Approved
0.7389	Intermediate Similarity	NPD3145	Approved
0.7389	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3060	Approved
0.7346	Intermediate Similarity	NPD1375	Discontinued
0.7342	Intermediate Similarity	NPD7477	Discontinued
0.7333	Intermediate Similarity	NPD7124	Phase 2
0.733	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6166	Phase 2
0.7326	Intermediate Similarity	NPD7773	Phase 2
0.7322	Intermediate Similarity	NPD7906	Approved
0.731	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7089	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4055	Discovery
0.7256	Intermediate Similarity	NPD4162	Approved
0.7256	Intermediate Similarity	NPD5177	Phase 3
0.7251	Intermediate Similarity	NPD5722	Discontinued
0.7244	Intermediate Similarity	NPD6584	Phase 3
0.7225	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6746	Phase 2
0.7184	Intermediate Similarity	NPD7831	Phase 2
0.7184	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7833	Phase 2
0.7176	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5718	Phase 2
0.7152	Intermediate Similarity	NPD4236	Phase 3
0.7152	Intermediate Similarity	NPD4237	Approved
0.7151	Intermediate Similarity	NPD1934	Approved
0.7143	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6841	Approved
0.7135	Intermediate Similarity	NPD6843	Phase 3
0.7135	Intermediate Similarity	NPD6842	Approved
0.7134	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6788	Approved
0.7125	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3687	Approved
0.7118	Intermediate Similarity	NPD3686	Approved
0.7117	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2922	Phase 1
0.7111	Intermediate Similarity	NPD7054	Approved
0.7108	Intermediate Similarity	NPD7466	Approved
0.7104	Intermediate Similarity	NPD7310	Approved
0.7104	Intermediate Similarity	NPD7313	Approved
0.7104	Intermediate Similarity	NPD7311	Approved
0.7104	Intermediate Similarity	NPD7312	Approved
0.7099	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD8070	Approved
0.7086	Intermediate Similarity	NPD5604	Discontinued
0.7072	Intermediate Similarity	NPD7472	Approved
0.7072	Intermediate Similarity	NPD7074	Phase 3
0.7066	Intermediate Similarity	NPD5241	Discontinued
0.7065	Intermediate Similarity	NPD7309	Approved
0.7055	Intermediate Similarity	NPD6111	Discontinued
0.7051	Intermediate Similarity	NPD2982	Phase 2
0.7051	Intermediate Similarity	NPD2983	Phase 2
0.7051	Intermediate Similarity	NPD6583	Phase 3
0.7051	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6582	Phase 2
0.7049	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7808	Phase 3
0.7043	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4739	Approved
0.7033	Intermediate Similarity	NPD7007	Discovery
0.7033	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1610	Phase 2
0.7022	Intermediate Similarity	NPD3051	Approved
0.7022	Intermediate Similarity	NPD6071	Discontinued
0.7019	Intermediate Similarity	NPD840	Approved
0.7019	Intermediate Similarity	NPD839	Approved
0.7018	Intermediate Similarity	NPD1653	Approved
0.7011	Intermediate Similarity	NPD4577	Approved
0.7011	Intermediate Similarity	NPD2978	Approved
0.7011	Intermediate Similarity	NPD4578	Approved
0.7011	Intermediate Similarity	NPD2977	Approved
0.7011	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5677	Discontinued
0.7006	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3489	Phase 3
0.6994	Remote Similarity	NPD3778	Approved
0.6993	Remote Similarity	NPD1548	Phase 1
0.6989	Remote Similarity	NPD4663	Approved
0.6987	Remote Similarity	NPD2981	Phase 2
0.6983	Remote Similarity	NPD2969	Approved
0.6983	Remote Similarity	NPD2970	Approved
0.6981	Remote Similarity	NPD3018	Phase 2
0.6973	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7228	Approved
0.6959	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2489	Approved
0.6944	Remote Similarity	NPD27	Approved
0.6943	Remote Similarity	NPD1669	Approved
0.6928	Remote Similarity	NPD3656	Approved
0.6928	Remote Similarity	NPD7266	Discontinued
0.6923	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8151	Discontinued
0.6914	Remote Similarity	NPD2801	Approved
0.6909	Remote Similarity	NPD4108	Discontinued
0.6902	Remote Similarity	NPD7039	Approved
0.6902	Remote Similarity	NPD7251	Discontinued
0.6902	Remote Similarity	NPD7038	Approved
0.6901	Remote Similarity	NPD1350	Approved
0.6901	Remote Similarity	NPD1351	Approved
0.6901	Remote Similarity	NPD1349	Approved
0.6899	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5089	Approved
0.6897	Remote Similarity	NPD5090	Approved
0.6895	Remote Similarity	NPD7125	Discontinued
0.6893	Remote Similarity	NPD6971	Discontinued
0.6891	Remote Similarity	NPD8095	Phase 1
0.6891	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.689	Remote Similarity	NPD3054	Approved
0.689	Remote Similarity	NPD3052	Approved
0.689	Remote Similarity	NPD5314	Approved
0.6886	Remote Similarity	NPD7037	Approved
0.6882	Remote Similarity	NPD1774	Approved
0.6879	Remote Similarity	NPD2235	Phase 2
0.6879	Remote Similarity	NPD2231	Phase 2
0.6875	Remote Similarity	NPD2861	Phase 2
0.6875	Remote Similarity	NPD2560	Approved
0.6875	Remote Similarity	NPD2563	Approved
0.6871	Remote Similarity	NPD2238	Phase 2
0.6864	Remote Similarity	NPD2677	Approved
0.6864	Remote Similarity	NPD3692	Discontinued
0.6854	Remote Similarity	NPD6234	Discontinued
0.6852	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5109	Approved
0.6852	Remote Similarity	NPD5110	Phase 2
0.6852	Remote Similarity	NPD5111	Phase 2
0.6848	Remote Similarity	NPD6797	Phase 2
0.6848	Remote Similarity	NPD6895	Approved
0.6848	Remote Similarity	NPD6896	Approved
0.6845	Remote Similarity	NPD6674	Discontinued
0.6842	Remote Similarity	NPD3985	Discontinued
0.6842	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3536	Discontinued
0.6839	Remote Similarity	NPD6502	Phase 2
0.6831	Remote Similarity	NPD5844	Phase 1
0.6818	Remote Similarity	NPD8455	Phase 2
0.681	Remote Similarity	NPD3530	Approved
0.681	Remote Similarity	NPD3531	Approved
0.681	Remote Similarity	NPD3532	Approved
0.679	Remote Similarity	NPD4625	Phase 3
0.6788	Remote Similarity	NPD2157	Approved
0.6788	Remote Similarity	NPD2568	Approved
0.6782	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3817	Phase 2
0.678	Remote Similarity	NPD6063	Approved
0.678	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7199	Phase 2

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