NPASS Compound

Structure

NPC127402 OpenBabel07101718182D 46 48 0 0 0 0 0 0 0 0999 V2000 -2.5981 -7.5000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 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 7.7942 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 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 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 -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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 8.6603 -2.0000 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 0.8660 -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 2.5981 -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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -5.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 45 1 0 0 0 0 3 46 1 0 0 0 0 4 5 1 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 9 1 0 0 0 0 6 22 2 0 0 0 0 7 10 2 0 0 0 0 7 22 1 0 0 0 0 8 11 1 0 0 0 0 8 24 1 0 0 0 0 9 25 2 0 0 0 0 10 25 1 0 0 0 0 11 32 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 0 0 0 0 13 35 1 0 0 0 0 14 37 1 0 0 0 0 15 36 1 0 0 0 0 16 23 1 0 0 0 0 16 27 2 0 0 0 0 17 23 2 0 0 0 0 17 30 1 0 0 0 0 18 23 1 0 0 0 0 18 31 2 0 0 0 0 19 24 2 0 0 0 0 19 28 1 0 0 0 0 20 26 2 0 0 0 0 20 29 1 0 0 0 0 21 35 2 3 0 0 0 21 38 1 0 0 0 0 24 26 1 0 0 0 0 25 39 1 0 0 0 0 26 27 1 0 0 0 0 27 34 1 0 0 0 0 28 29 2 0 0 0 0 28 40 1 0 0 0 0 29 41 1 0 0 0 0 30 33 2 0 0 0 0 30 45 1 0 0 0 0 31 33 1 0 0 0 0 31 46 1 0 0 0 0 32 36 2 3 0 0 0 32 42 1 0 0 0 0 33 43 1 0 0 0 0 34 37 2 3 0 0 0 34 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	635.28
Volume:	648.779
LogP:	1.45
LogD:	2.136
LogS:	-3.953
# Rotatable Bonds:	19
TPSA:	186.68
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.054
Synthetic Accessibility Score:	2.985
Fsp3:	0.324
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.931
MDCK Permeability:	1.266218168893829e-05
Pgp-inhibitor:	0.939
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.926
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	95.32512664794922%
Volume Distribution (VD):	0.967
Pgp-substrate:	2.938884973526001%

ADMET: Metabolism

CYP1A2-inhibitor:	0.191
CYP1A2-substrate:	0.603
CYP2C19-inhibitor:	0.154
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.46
CYP2C9-substrate:	0.714
CYP2D6-inhibitor:	0.474
CYP2D6-substrate:	0.429
CYP3A4-inhibitor:	0.842
CYP3A4-substrate:	0.147

ADMET: Excretion

Clearance (CL):	7.233
Half-life (T1/2):	0.949

ADMET: Toxicity

hERG Blockers:	0.11
Human Hepatotoxicity (H-HT):	0.396
Drug-inuced Liver Injury (DILI):	0.248
AMES Toxicity:	0.126
Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.839
Carcinogencity:	0.009
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.012

Download Data

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

Natural Product: NPC127402

Natural Product ID:	NPC127402
*Common Name:**	(E)-2-(4,5-Dihydroxy-2-{3-[(4-Hydroxyphenethyl)Amino]-3-Oxopropyl}Phenyl)-3-(4-Hydroxy-3,5-Dimethoxyphenyl)-N-(4-Acetamidobutyl)Acrylamide
IUPAC Name:	(E)-N-(4-acetamidobutyl)-2-[4,5-dihydroxy-2-[3-[2-(4-hydroxyphenyl)ethylamino]-3-oxopropyl]phenyl]-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enamide
Synonyms:
Standard InCHIKey:	HJDHQNBCJWHUOS-JVWAILMASA-N
Standard InCHI:	InChI=1S/C34H41N3O9/c1-21(38)35-13-4-5-14-37-34(44)27(16-23-17-30(45-2)33(43)31(18-23)46-3)26-20-29(41)28(40)19-24(26)8-11-32(42)36-15-12-22-6-9-25(39)10-7-22/h6-7,9-10,16-20,39-41,43H,4-5,8,11-15H2,1-3H3,(H,35,38)(H,36,42)(H,37,44)/b27-16+
SMILES:	COc1cc(/C=C(c2cc(O)c(cc2CCC(=NCCc2ccc(cc2)O)O)O)/C(=NCCCCN=C(O)C)O)cc(c1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337119
PubChem CID:	71524308
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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	=	52700.0	nM	PMID[485079]
NPT1	Others	Radical scavenging activity		IC50	=	64700.0	nM	PMID[485079]

☑ 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 NPC127402 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	255
0.1-0.2	1364
0.2-0.3	6209
0.3-0.4	12329
0.4-0.5	4788
0.5-0.6	7494
0.6-0.7	7913
0.7-0.8	2161
0.8-0.85	154
0.85-0.9	23
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9793	High Similarity	NPC107602
0.9577	High Similarity	NPC5462
0.9155	High Similarity	NPC296898
0.8961	High Similarity	NPC50380
0.8961	High Similarity	NPC179250
0.8836	High Similarity	NPC100478
0.8836	High Similarity	NPC222039
0.8662	High Similarity	NPC114102
0.863	High Similarity	NPC299583
0.8609	High Similarity	NPC471032
0.8609	High Similarity	NPC470935
0.8601	High Similarity	NPC214869
0.8592	High Similarity	NPC35961
0.8592	High Similarity	NPC195749
0.8592	High Similarity	NPC52029
0.8562	High Similarity	NPC160607
0.8562	High Similarity	NPC204848
0.8562	High Similarity	NPC312770
0.8562	High Similarity	NPC41473
0.8562	High Similarity	NPC14600
0.8553	High Similarity	NPC90984
0.8521	High Similarity	NPC155838
0.8514	High Similarity	NPC472090
0.8514	High Similarity	NPC472092
0.8514	High Similarity	NPC472091
0.8471	Intermediate Similarity	NPC329837
0.8451	Intermediate Similarity	NPC186898
0.8451	Intermediate Similarity	NPC251571
0.84	Intermediate Similarity	NPC472088
0.84	Intermediate Similarity	NPC472087
0.8387	Intermediate Similarity	NPC275027
0.8333	Intermediate Similarity	NPC472089
0.8323	Intermediate Similarity	NPC52475
0.8322	Intermediate Similarity	NPC153990
0.8301	Intermediate Similarity	NPC277857
0.8301	Intermediate Similarity	NPC115144
0.8288	Intermediate Similarity	NPC14224
0.8288	Intermediate Similarity	NPC161958
0.8276	Intermediate Similarity	NPC126836
0.8269	Intermediate Similarity	NPC18614
0.8252	Intermediate Similarity	NPC301713
0.8246	Intermediate Similarity	NPC318805
0.8246	Intermediate Similarity	NPC41122
0.8243	Intermediate Similarity	NPC313081
0.8243	Intermediate Similarity	NPC200557
0.8243	Intermediate Similarity	NPC294884
0.8243	Intermediate Similarity	NPC158142
0.8243	Intermediate Similarity	NPC69029
0.8243	Intermediate Similarity	NPC108198
0.8243	Intermediate Similarity	NPC10314
0.8232	Intermediate Similarity	NPC231371
0.8217	Intermediate Similarity	NPC475557
0.82	Intermediate Similarity	NPC55947
0.82	Intermediate Similarity	NPC275061
0.82	Intermediate Similarity	NPC132804
0.82	Intermediate Similarity	NPC220344
0.82	Intermediate Similarity	NPC243996
0.8194	Intermediate Similarity	NPC127587
0.8188	Intermediate Similarity	NPC143139
0.8188	Intermediate Similarity	NPC202846
0.8182	Intermediate Similarity	NPC233410
0.8182	Intermediate Similarity	NPC116907
0.8182	Intermediate Similarity	NPC298757
0.8182	Intermediate Similarity	NPC251855
0.8182	Intermediate Similarity	NPC472093
0.8182	Intermediate Similarity	NPC57490
0.8182	Intermediate Similarity	NPC117214
0.8182	Intermediate Similarity	NPC203133
0.8182	Intermediate Similarity	NPC221077
0.8182	Intermediate Similarity	NPC193544
0.8182	Intermediate Similarity	NPC475169
0.8182	Intermediate Similarity	NPC17943
0.8182	Intermediate Similarity	NPC208950
0.8176	Intermediate Similarity	NPC195766
0.8176	Intermediate Similarity	NPC206736
0.8176	Intermediate Similarity	NPC125649
0.8163	Intermediate Similarity	NPC285078
0.8163	Intermediate Similarity	NPC6854
0.8163	Intermediate Similarity	NPC313737
0.8146	Intermediate Similarity	NPC12668
0.8146	Intermediate Similarity	NPC308768
0.8146	Intermediate Similarity	NPC266197
0.8146	Intermediate Similarity	NPC291101
0.8133	Intermediate Similarity	NPC230919
0.8133	Intermediate Similarity	NPC56329
0.8133	Intermediate Similarity	NPC22902
0.8133	Intermediate Similarity	NPC266453
0.8133	Intermediate Similarity	NPC200935
0.8133	Intermediate Similarity	NPC242715
0.8129	Intermediate Similarity	NPC262297
0.8125	Intermediate Similarity	NPC28730
0.8125	Intermediate Similarity	NPC18924
0.8125	Intermediate Similarity	NPC103823
0.8125	Intermediate Similarity	NPC214406
0.8125	Intermediate Similarity	NPC44748
0.8125	Intermediate Similarity	NPC76451
0.8125	Intermediate Similarity	NPC78974
0.8125	Intermediate Similarity	NPC223136
0.8121	Intermediate Similarity	NPC241241
0.8108	Intermediate Similarity	NPC32778
0.8105	Intermediate Similarity	NPC469630
0.8099	Intermediate Similarity	NPC262253
0.8099	Intermediate Similarity	NPC473411
0.8099	Intermediate Similarity	NPC71579
0.8095	Intermediate Similarity	NPC470095
0.8095	Intermediate Similarity	NPC130595
0.8095	Intermediate Similarity	NPC93882
0.8095	Intermediate Similarity	NPC15543
0.8095	Intermediate Similarity	NPC470096
0.8079	Intermediate Similarity	NPC212942
0.8079	Intermediate Similarity	NPC79622
0.8079	Intermediate Similarity	NPC243759
0.8079	Intermediate Similarity	NPC29868
0.8079	Intermediate Similarity	NPC218131
0.8079	Intermediate Similarity	NPC6300
0.8079	Intermediate Similarity	NPC477838
0.8079	Intermediate Similarity	NPC477837
0.8079	Intermediate Similarity	NPC230124
0.8079	Intermediate Similarity	NPC114171
0.8079	Intermediate Similarity	NPC22517
0.8079	Intermediate Similarity	NPC105847
0.8079	Intermediate Similarity	NPC184613
0.8072	Intermediate Similarity	NPC474051
0.8069	Intermediate Similarity	NPC282000
0.8069	Intermediate Similarity	NPC293054
0.8069	Intermediate Similarity	NPC236791
0.8069	Intermediate Similarity	NPC124452
0.8069	Intermediate Similarity	NPC246620
0.8069	Intermediate Similarity	NPC159968
0.8069	Intermediate Similarity	NPC210355
0.8069	Intermediate Similarity	NPC324112
0.8069	Intermediate Similarity	NPC74817
0.8069	Intermediate Similarity	NPC169474
0.8069	Intermediate Similarity	NPC82679
0.8067	Intermediate Similarity	NPC30632
0.8057	Intermediate Similarity	NPC234318
0.8057	Intermediate Similarity	NPC281629
0.8056	Intermediate Similarity	NPC60885
0.8056	Intermediate Similarity	NPC299584
0.8056	Intermediate Similarity	NPC234400
0.8056	Intermediate Similarity	NPC82483
0.8056	Intermediate Similarity	NPC265483
0.8054	Intermediate Similarity	NPC209199
0.8054	Intermediate Similarity	NPC160697
0.8046	Intermediate Similarity	NPC85381
0.8042	Intermediate Similarity	NPC228922
0.8042	Intermediate Similarity	NPC282496
0.8042	Intermediate Similarity	NPC136319
0.8042	Intermediate Similarity	NPC233526
0.8042	Intermediate Similarity	NPC197757
0.8039	Intermediate Similarity	NPC277784
0.8039	Intermediate Similarity	NPC183709
0.8039	Intermediate Similarity	NPC175838
0.8025	Intermediate Similarity	NPC476969
0.8023	Intermediate Similarity	NPC29531
0.8014	Intermediate Similarity	NPC206615
0.8014	Intermediate Similarity	NPC470213
0.8014	Intermediate Similarity	NPC186843
0.8014	Intermediate Similarity	NPC98631
0.8014	Intermediate Similarity	NPC154866
0.8013	Intermediate Similarity	NPC6262
0.8013	Intermediate Similarity	NPC151656
0.8013	Intermediate Similarity	NPC201145
0.8013	Intermediate Similarity	NPC73535
0.8013	Intermediate Similarity	NPC90615
0.8013	Intermediate Similarity	NPC25111
0.8013	Intermediate Similarity	NPC272157
0.8013	Intermediate Similarity	NPC266006
0.8	Intermediate Similarity	NPC30779
0.7988	Intermediate Similarity	NPC68328
0.7987	Intermediate Similarity	NPC218530
0.7986	Intermediate Similarity	NPC206487
0.7986	Intermediate Similarity	NPC5796
0.7973	Intermediate Similarity	NPC474017
0.7972	Intermediate Similarity	NPC41562
0.7962	Intermediate Similarity	NPC182119
0.7959	Intermediate Similarity	NPC170844
0.7959	Intermediate Similarity	NPC58164
0.7959	Intermediate Similarity	NPC10225
0.7959	Intermediate Similarity	NPC476968
0.7958	Intermediate Similarity	NPC166759
0.795	Intermediate Similarity	NPC235628
0.7949	Intermediate Similarity	NPC126291
0.7947	Intermediate Similarity	NPC476639
0.7947	Intermediate Similarity	NPC300846
0.7947	Intermediate Similarity	NPC254610
0.7947	Intermediate Similarity	NPC114155
0.7947	Intermediate Similarity	NPC205442
0.7945	Intermediate Similarity	NPC470699
0.7945	Intermediate Similarity	NPC266555
0.7941	Intermediate Similarity	NPC286119
0.7935	Intermediate Similarity	NPC470097
0.7935	Intermediate Similarity	NPC114119
0.7935	Intermediate Similarity	NPC471415
0.7933	Intermediate Similarity	NPC188378
0.7933	Intermediate Similarity	NPC170694
0.7933	Intermediate Similarity	NPC7515
0.7933	Intermediate Similarity	NPC276026
0.7933	Intermediate Similarity	NPC555
0.7933	Intermediate Similarity	NPC469659

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 NPC127402 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	723
0.2-0.3	1136
0.3-0.4	2382
0.4-0.5	2456
0.5-0.6	1440
0.6-0.7	736
0.7-0.8	101
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8442	Intermediate Similarity	NPD4005	Discontinued
0.8187	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD4675	Approved
0.8153	Intermediate Similarity	NPD4678	Approved
0.8095	Intermediate Similarity	NPD2674	Phase 3
0.7963	Intermediate Similarity	NPD4055	Discovery
0.7959	Intermediate Similarity	NPD3027	Phase 3
0.7922	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD3145	Approved
0.7905	Intermediate Similarity	NPD3144	Approved
0.7898	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD8053	Approved
0.7895	Intermediate Similarity	NPD8054	Approved
0.7834	Intermediate Similarity	NPD4123	Phase 3
0.7821	Intermediate Similarity	NPD7124	Phase 2
0.7771	Intermediate Similarity	NPD4357	Discontinued
0.7756	Intermediate Similarity	NPD2219	Phase 1
0.7692	Intermediate Similarity	NPD6331	Phase 2
0.7671	Intermediate Similarity	NPD1669	Approved
0.764	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD1558	Phase 1
0.7558	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD5111	Phase 2
0.755	Intermediate Similarity	NPD5109	Approved
0.755	Intermediate Similarity	NPD5110	Phase 2
0.7546	Intermediate Similarity	NPD5090	Approved
0.7546	Intermediate Similarity	NPD5089	Approved
0.7533	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5241	Discontinued
0.7532	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6111	Discontinued
0.7516	Intermediate Similarity	NPD3060	Approved
0.75	Intermediate Similarity	NPD2922	Phase 1
0.7486	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD8251	Approved
0.7485	Intermediate Similarity	NPD8252	Approved
0.7485	Intermediate Similarity	NPD8099	Discontinued
0.7468	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5772	Approved
0.7455	Intermediate Similarity	NPD5773	Approved
0.7452	Intermediate Similarity	NPD7153	Discontinued
0.7451	Intermediate Similarity	NPD1613	Approved
0.7451	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD8156	Discontinued
0.744	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2161	Phase 2
0.7434	Intermediate Similarity	NPD5718	Phase 2
0.7432	Intermediate Similarity	NPD2983	Phase 2
0.7432	Intermediate Similarity	NPD2982	Phase 2
0.7391	Intermediate Similarity	NPD7447	Phase 1
0.7389	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2981	Phase 2
0.7351	Intermediate Similarity	NPD3018	Phase 2
0.7349	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7526	Approved
0.7346	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD52	Approved
0.7337	Intermediate Similarity	NPD6746	Phase 2
0.7333	Intermediate Similarity	NPD6072	Discontinued
0.7315	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6895	Approved
0.7308	Intermediate Similarity	NPD6896	Approved
0.7303	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4908	Phase 1
0.7301	Intermediate Similarity	NPD2122	Discontinued
0.7284	Intermediate Similarity	NPD4739	Approved
0.7278	Intermediate Similarity	NPD1375	Discontinued
0.7263	Intermediate Similarity	NPD7906	Approved
0.7262	Intermediate Similarity	NPD6788	Approved
0.7261	Intermediate Similarity	NPD4108	Discontinued
0.7254	Intermediate Similarity	NPD228	Approved
0.7248	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1350	Approved
0.7239	Intermediate Similarity	NPD1349	Approved
0.7239	Intermediate Similarity	NPD1351	Approved
0.7233	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7212	Phase 2
0.7222	Intermediate Similarity	NPD7213	Phase 3
0.7219	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5604	Discontinued
0.7219	Intermediate Similarity	NPD7831	Phase 2
0.7219	Intermediate Similarity	NPD7833	Phase 2
0.7208	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4236	Phase 3
0.7188	Intermediate Similarity	NPD7827	Phase 1
0.7188	Intermediate Similarity	NPD4237	Approved
0.7188	Intermediate Similarity	NPD5177	Phase 3
0.7184	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6234	Discontinued
0.7171	Intermediate Similarity	NPD6584	Phase 3
0.7161	Intermediate Similarity	NPD7477	Discontinued
0.7153	Intermediate Similarity	NPD5283	Phase 1
0.7143	Intermediate Similarity	NPD2978	Approved
0.7143	Intermediate Similarity	NPD2977	Approved
0.7134	Intermediate Similarity	NPD4097	Suspended
0.7126	Intermediate Similarity	NPD3489	Phase 3
0.7115	Intermediate Similarity	NPD3620	Phase 2
0.7115	Intermediate Similarity	NPD2238	Phase 2
0.7115	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD37	Approved
0.7081	Intermediate Similarity	NPD4162	Approved
0.7079	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7549	Discontinued
0.7073	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6843	Phase 3
0.7072	Intermediate Similarity	NPD6842	Approved
0.7072	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6841	Approved
0.7062	Intermediate Similarity	NPD7007	Discovery
0.7059	Intermediate Similarity	NPD7773	Phase 2
0.7059	Intermediate Similarity	NPD7451	Discontinued
0.7052	Intermediate Similarity	NPD6232	Discontinued
0.7052	Intermediate Similarity	NPD6071	Discontinued
0.7051	Intermediate Similarity	NPD840	Approved
0.7051	Intermediate Similarity	NPD839	Approved
0.7047	Intermediate Similarity	NPD2668	Approved
0.7047	Intermediate Similarity	NPD2667	Approved
0.7041	Intermediate Similarity	NPD7089	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5310	Approved
0.7039	Intermediate Similarity	NPD5311	Approved
0.7032	Intermediate Similarity	NPD4625	Phase 3
0.7032	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1024	Discontinued
0.7029	Intermediate Similarity	NPD7473	Discontinued
0.7029	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2157	Approved
0.7025	Intermediate Similarity	NPD5314	Approved
0.7024	Intermediate Similarity	NPD7438	Suspended
0.702	Intermediate Similarity	NPD2230	Approved
0.702	Intermediate Similarity	NPD2233	Approved
0.702	Intermediate Similarity	NPD2232	Approved
0.7019	Intermediate Similarity	NPD2808	Discontinued
0.7019	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1712	Approved
0.7011	Intermediate Similarity	NPD4083	Discontinued
0.7	Intermediate Similarity	NPD2560	Approved
0.7	Intermediate Similarity	NPD2563	Approved
0.6994	Remote Similarity	NPD7199	Phase 2
0.6994	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7228	Approved
0.6988	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4093	Discontinued
0.6974	Remote Similarity	NPD6583	Phase 3
0.6974	Remote Similarity	NPD6582	Phase 2
0.6971	Remote Similarity	NPD2489	Approved
0.6971	Remote Similarity	NPD27	Approved
0.697	Remote Similarity	NPD4584	Approved
0.697	Remote Similarity	NPD1424	Approved
0.6959	Remote Similarity	NPD4966	Approved
0.6959	Remote Similarity	NPD4965	Approved
0.6959	Remote Similarity	NPD4967	Phase 2
0.6954	Remote Similarity	NPD1610	Phase 2
0.6954	Remote Similarity	NPD4010	Discontinued
0.6954	Remote Similarity	NPD3051	Approved
0.6946	Remote Similarity	NPD2883	Discontinued
0.6944	Remote Similarity	NPD7313	Approved
0.6944	Remote Similarity	NPD4577	Approved
0.6944	Remote Similarity	NPD7312	Approved
0.6944	Remote Similarity	NPD7311	Approved
0.6944	Remote Similarity	NPD7310	Approved
0.6944	Remote Similarity	NPD4578	Approved
0.6943	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD2801	Approved
0.6937	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7466	Approved
0.6927	Remote Similarity	NPD7263	Phase 2
0.6923	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7110	Phase 1
0.6923	Remote Similarity	NPD4663	Approved
0.6923	Remote Similarity	NPD3778	Approved
0.6923	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6971	Discontinued
0.6918	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7037	Approved
0.6914	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2970	Approved
0.6914	Remote Similarity	NPD2969	Approved
0.6913	Remote Similarity	NPD1548	Phase 1
0.6909	Remote Similarity	NPD6087	Phase 1
0.6909	Remote Similarity	NPD5297	Approved
0.6906	Remote Similarity	NPD7309	Approved
0.6899	Remote Similarity	NPD3062	Approved
0.6899	Remote Similarity	NPD3059	Approved
0.6899	Remote Similarity	NPD3061	Approved
0.6897	Remote Similarity	NPD7802	Discontinued
0.689	Remote Similarity	NPD3692	Discontinued
0.689	Remote Similarity	NPD2677	Approved
0.6886	Remote Similarity	NPD6031	Approved
0.6886	Remote Similarity	NPD6030	Approved
0.6883	Remote Similarity	NPD3053	Approved
0.6883	Remote Similarity	NPD3055	Approved
0.6882	Remote Similarity	NPD1934	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