NPASS Compound

Structure

NPC219664 OpenBabel07101719152D 23 25 0 0 1 0 0 0 0 0999 V2000 -2.4538 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 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 17 1 0 0 0 0 2 17 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 7 2 0 0 0 0 6 9 1 0 0 0 0 7 11 1 0 0 0 0 8 10 1 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 20 1 0 0 0 0 12 17 1 6 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 18 2 0 0 0 0 16 23 1 0 0 0 0 17 19 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	319.14
Volume:	318.684
LogP:	2.796
LogD:	2.798
LogS:	-2.495
# Rotatable Bonds:	4
TPSA:	70.04
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.933
Synthetic Accessibility Score:	3.347
Fsp3:	0.471
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.671
MDCK Permeability:	2.39554083236726e-05
Pgp-inhibitor:	0.537
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.24
Plasma Protein Binding (PPB):	89.08223724365234%
Volume Distribution (VD):	0.642
Pgp-substrate:	10.673580169677734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.425
CYP1A2-substrate:	0.923
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.882
CYP2C9-inhibitor:	0.058
CYP2C9-substrate:	0.83
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.774
CYP3A4-inhibitor:	0.226
CYP3A4-substrate:	0.533

ADMET: Excretion

Clearance (CL):	6.966
Half-life (T1/2):	0.359

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.511
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.435
Maximum Recommended Daily Dose:	0.111
Skin Sensitization:	0.451
Carcinogencity:	0.218
Eye Corrosion:	0.003
Eye Irritation:	0.026
Respiratory Toxicity:	0.788

Download Data

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

Natural Product: NPC219664

Natural Product ID:	NPC219664
*Common Name:**	(S)-(-)-7,8-Dimethyoxyplatydesmine
IUPAC Name:	2-[(2S)-4,7,8-trimethoxy-2,3-dihydrofuro[2,3-b]quinolin-2-yl]propan-2-ol
Synonyms:
Standard InCHIKey:	KEQCVKMHHPQLBP-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C17H21NO5/c1-17(2,19)12-8-10-14(21-4)9-6-7-11(20-3)15(22-5)13(9)18-16(10)23-12/h6-7,12,19H,8H2,1-5H3/t12-/m0/s1
SMILES:	CC(C)([C@@H]1Cc2c(c3ccc(c(c3nc2O1)OC)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463650
PubChem CID:	10426085
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001780] Dihydrofuranoquinolines

*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
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575945]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18163582]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	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
Others	4

Activity Type	# Activity
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	86.5	%	PMID[488855]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	81.7	%	PMID[488855]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	84.4	%	PMID[488855]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	89.8	%	PMID[488855]

☑ 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 NPC219664 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	511
0.1-0.2	2494
0.2-0.3	13025
0.3-0.4	5088
0.4-0.5	12015
0.5-0.6	8101
0.6-0.7	1223
0.7-0.8	224
0.8-0.85	10
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC203168
0.9211	High Similarity	NPC66815
0.8691	High Similarity	NPC279401
0.8691	High Similarity	NPC79293
0.8611	High Similarity	NPC58209
0.8387	Intermediate Similarity	NPC166712
0.8357	Intermediate Similarity	NPC148409
0.8349	Intermediate Similarity	NPC160100
0.8294	Intermediate Similarity	NPC200888
0.8279	Intermediate Similarity	NPC34770
0.8177	Intermediate Similarity	NPC474595
0.8135	Intermediate Similarity	NPC42591
0.8116	Intermediate Similarity	NPC474594
0.8083	Intermediate Similarity	NPC62069
0.8047	Intermediate Similarity	NPC476997
0.8018	Intermediate Similarity	NPC188400
0.8018	Intermediate Similarity	NPC208364
0.8009	Intermediate Similarity	NPC476998
0.8009	Intermediate Similarity	NPC476996
0.8	Intermediate Similarity	NPC203373
0.7963	Intermediate Similarity	NPC476994
0.7951	Intermediate Similarity	NPC304183
0.7902	Intermediate Similarity	NPC470930
0.7876	Intermediate Similarity	NPC173250
0.7868	Intermediate Similarity	NPC66083
0.7837	Intermediate Similarity	NPC209769
0.7824	Intermediate Similarity	NPC283152
0.7727	Intermediate Similarity	NPC217176
0.7727	Intermediate Similarity	NPC204385
0.772	Intermediate Similarity	NPC312872
0.7718	Intermediate Similarity	NPC199277
0.7718	Intermediate Similarity	NPC135887
0.7713	Intermediate Similarity	NPC476995
0.7689	Intermediate Similarity	NPC101312
0.768	Intermediate Similarity	NPC194724
0.7672	Intermediate Similarity	NPC120513
0.7662	Intermediate Similarity	NPC469390
0.7647	Intermediate Similarity	NPC476999
0.7632	Intermediate Similarity	NPC118511
0.7628	Intermediate Similarity	NPC473822
0.7628	Intermediate Similarity	NPC469594
0.7623	Intermediate Similarity	NPC277351
0.7591	Intermediate Similarity	NPC140296
0.759	Intermediate Similarity	NPC288943
0.7583	Intermediate Similarity	NPC469589
0.7546	Intermediate Similarity	NPC131885
0.7534	Intermediate Similarity	NPC205372
0.7525	Intermediate Similarity	NPC206201
0.75	Intermediate Similarity	NPC314552
0.75	Intermediate Similarity	NPC473182
0.7489	Intermediate Similarity	NPC168922
0.7488	Intermediate Similarity	NPC128823
0.7478	Intermediate Similarity	NPC473183
0.7477	Intermediate Similarity	NPC26679
0.7476	Intermediate Similarity	NPC137929
0.7476	Intermediate Similarity	NPC164374
0.7465	Intermediate Similarity	NPC173080
0.7463	Intermediate Similarity	NPC61350
0.7454	Intermediate Similarity	NPC288349
0.7442	Intermediate Similarity	NPC469592
0.7442	Intermediate Similarity	NPC471080
0.7441	Intermediate Similarity	NPC476106
0.7441	Intermediate Similarity	NPC471736
0.7441	Intermediate Similarity	NPC472111
0.7437	Intermediate Similarity	NPC474798
0.7421	Intermediate Similarity	NPC97746
0.7416	Intermediate Similarity	NPC470586
0.7415	Intermediate Similarity	NPC475190
0.7389	Intermediate Similarity	NPC473184
0.7373	Intermediate Similarity	NPC470799
0.7373	Intermediate Similarity	NPC8022
0.7371	Intermediate Similarity	NPC308392
0.7371	Intermediate Similarity	NPC470931
0.7363	Intermediate Similarity	NPC320394
0.7361	Intermediate Similarity	NPC162530
0.7352	Intermediate Similarity	NPC298436
0.7352	Intermediate Similarity	NPC473179
0.7346	Intermediate Similarity	NPC469440
0.7346	Intermediate Similarity	NPC162484
0.7336	Intermediate Similarity	NPC185782
0.7333	Intermediate Similarity	NPC201508
0.7333	Intermediate Similarity	NPC31930
0.7318	Intermediate Similarity	NPC174049
0.7315	Intermediate Similarity	NPC316981
0.7315	Intermediate Similarity	NPC112206
0.7315	Intermediate Similarity	NPC202605
0.7304	Intermediate Similarity	NPC110741
0.7299	Intermediate Similarity	NPC291535
0.7299	Intermediate Similarity	NPC475085
0.7299	Intermediate Similarity	NPC475112
0.7296	Intermediate Similarity	NPC1608
0.7296	Intermediate Similarity	NPC472068
0.7282	Intermediate Similarity	NPC195268
0.7282	Intermediate Similarity	NPC133140
0.7277	Intermediate Similarity	NPC473188
0.7273	Intermediate Similarity	NPC124300
0.7273	Intermediate Similarity	NPC72211
0.7269	Intermediate Similarity	NPC255800
0.7269	Intermediate Similarity	NPC96584
0.7264	Intermediate Similarity	NPC118776
0.7263	Intermediate Similarity	NPC26872
0.726	Intermediate Similarity	NPC473513
0.7252	Intermediate Similarity	NPC118121
0.7252	Intermediate Similarity	NPC122463
0.725	Intermediate Similarity	NPC472168
0.7241	Intermediate Similarity	NPC291609
0.7235	Intermediate Similarity	NPC48353
0.7232	Intermediate Similarity	NPC202503
0.723	Intermediate Similarity	NPC16452
0.723	Intermediate Similarity	NPC476581
0.723	Intermediate Similarity	NPC36229
0.7229	Intermediate Similarity	NPC475844
0.7227	Intermediate Similarity	NPC204446
0.7225	Intermediate Similarity	NPC243834
0.7225	Intermediate Similarity	NPC70956
0.722	Intermediate Similarity	NPC242928
0.7214	Intermediate Similarity	NPC478032
0.7204	Intermediate Similarity	NPC11017
0.7204	Intermediate Similarity	NPC234197
0.7202	Intermediate Similarity	NPC266931
0.72	Intermediate Similarity	NPC473185
0.7198	Intermediate Similarity	NPC280964
0.7198	Intermediate Similarity	NPC141915
0.7198	Intermediate Similarity	NPC114335
0.7183	Intermediate Similarity	NPC475774
0.7181	Intermediate Similarity	NPC475253
0.7179	Intermediate Similarity	NPC310618
0.7177	Intermediate Similarity	NPC473053
0.7177	Intermediate Similarity	NPC70259
0.7169	Intermediate Similarity	NPC235076
0.7163	Intermediate Similarity	NPC193777
0.7156	Intermediate Similarity	NPC476578
0.7156	Intermediate Similarity	NPC476582
0.7156	Intermediate Similarity	NPC53069
0.7156	Intermediate Similarity	NPC296482
0.7156	Intermediate Similarity	NPC4071
0.7156	Intermediate Similarity	NPC202768
0.7155	Intermediate Similarity	NPC99891
0.715	Intermediate Similarity	NPC26850
0.7149	Intermediate Similarity	NPC100079
0.7149	Intermediate Similarity	NPC23614
0.7143	Intermediate Similarity	NPC188420
0.7143	Intermediate Similarity	NPC272706
0.713	Intermediate Similarity	NPC475910
0.7129	Intermediate Similarity	NPC43787
0.7129	Intermediate Similarity	NPC131017
0.7129	Intermediate Similarity	NPC205934
0.7123	Intermediate Similarity	NPC149471
0.7123	Intermediate Similarity	NPC271215
0.7108	Intermediate Similarity	NPC84478
0.7103	Intermediate Similarity	NPC223427
0.7097	Intermediate Similarity	NPC201697
0.7095	Intermediate Similarity	NPC129897
0.7089	Intermediate Similarity	NPC472067
0.7089	Intermediate Similarity	NPC267423
0.7089	Intermediate Similarity	NPC472066
0.7089	Intermediate Similarity	NPC472031
0.7085	Intermediate Similarity	NPC132642
0.7083	Intermediate Similarity	NPC313189
0.7078	Intermediate Similarity	NPC209981
0.7074	Intermediate Similarity	NPC469554
0.7073	Intermediate Similarity	NPC62510
0.707	Intermediate Similarity	NPC264166
0.707	Intermediate Similarity	NPC47059
0.707	Intermediate Similarity	NPC118832
0.707	Intermediate Similarity	NPC165349
0.707	Intermediate Similarity	NPC274291
0.707	Intermediate Similarity	NPC329708
0.7069	Intermediate Similarity	NPC470785
0.7064	Intermediate Similarity	NPC472434
0.7062	Intermediate Similarity	NPC224928
0.7061	Intermediate Similarity	NPC469792
0.7054	Intermediate Similarity	NPC477532
0.7048	Intermediate Similarity	NPC110151
0.7042	Intermediate Similarity	NPC477019
0.704	Intermediate Similarity	NPC208084
0.704	Intermediate Similarity	NPC46451
0.7039	Intermediate Similarity	NPC314573
0.7035	Intermediate Similarity	NPC179287
0.7033	Intermediate Similarity	NPC294244
0.7032	Intermediate Similarity	NPC146418
0.7026	Intermediate Similarity	NPC184680
0.7025	Intermediate Similarity	NPC284685
0.7022	Intermediate Similarity	NPC280272
0.7018	Intermediate Similarity	NPC252251
0.7014	Intermediate Similarity	NPC16066
0.7009	Intermediate Similarity	NPC476044
0.7009	Intermediate Similarity	NPC128115
0.7009	Intermediate Similarity	NPC54066
0.7	Intermediate Similarity	NPC252590
0.7	Intermediate Similarity	NPC96405
0.7	Intermediate Similarity	NPC171409
0.6992	Remote Similarity	NPC227824
0.6992	Remote Similarity	NPC284141
0.6986	Remote Similarity	NPC290689
0.6986	Remote Similarity	NPC269367
0.6986	Remote Similarity	NPC199667
0.6966	Remote Similarity	NPC41501
0.6963	Remote Similarity	NPC329747
0.696	Remote Similarity	NPC473449

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 NPC219664 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	662
0.2-0.3	1055
0.3-0.4	1934
0.4-0.5	2813
0.5-0.6	1790
0.6-0.7	544
0.7-0.8	43
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7897	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6494	Phase 2
0.7736	Intermediate Similarity	NPD5903	Approved
0.7736	Intermediate Similarity	NPD5902	Approved
0.7671	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD5256	Discontinued
0.7602	Intermediate Similarity	NPD3920	Phase 2
0.7571	Intermediate Similarity	NPD7222	Phase 2
0.7536	Intermediate Similarity	NPD5658	Approved
0.7524	Intermediate Similarity	NPD3003	Approved
0.7512	Intermediate Similarity	NPD4502	Phase 2
0.7512	Intermediate Similarity	NPD3875	Discontinued
0.7512	Intermediate Similarity	NPD6550	Discontinued
0.75	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5164	Discontinued
0.7488	Intermediate Similarity	NPD1768	Approved
0.7474	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD6590	Discontinued
0.7463	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD4203	Approved
0.7437	Intermediate Similarity	NPD4204	Approved
0.7422	Intermediate Similarity	NPD7558	Phase 2
0.7406	Intermediate Similarity	NPD7453	Approved
0.7406	Intermediate Similarity	NPD7452	Approved
0.7343	Intermediate Similarity	NPD5512	Phase 3
0.7336	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD5930	Phase 3
0.7282	Intermediate Similarity	NPD3924	Approved
0.7282	Intermediate Similarity	NPD3923	Approved
0.7282	Intermediate Similarity	NPD3921	Approved
0.7282	Intermediate Similarity	NPD3922	Approved
0.7277	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD4131	Phase 3
0.7246	Intermediate Similarity	NPD7859	Phase 2
0.7243	Intermediate Similarity	NPD1392	Approved
0.7238	Intermediate Similarity	NPD2175	Phase 3
0.7238	Intermediate Similarity	NPD2176	Approved
0.7238	Intermediate Similarity	NPD2177	Approved
0.7227	Intermediate Similarity	NPD6985	Discontinued
0.7215	Intermediate Similarity	NPD5612	Discontinued
0.7212	Intermediate Similarity	NPD4418	Discontinued
0.7198	Intermediate Similarity	NPD4876	Phase 3
0.7198	Intermediate Similarity	NPD4875	Phase 3
0.7196	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7194	Discontinued
0.7163	Intermediate Similarity	NPD5429	Discontinued
0.7163	Intermediate Similarity	NPD7125	Discontinued
0.7162	Intermediate Similarity	NPD6963	Approved
0.7162	Intermediate Similarity	NPD6964	Approved
0.7156	Intermediate Similarity	NPD3816	Phase 1
0.7156	Intermediate Similarity	NPD3815	Phase 1
0.7143	Intermediate Similarity	NPD6988	Phase 1
0.7131	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7169	Suspended
0.7101	Intermediate Similarity	NPD2845	Phase 2
0.7101	Intermediate Similarity	NPD2843	Phase 2
0.7089	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6290	Phase 2
0.707	Intermediate Similarity	NPD4038	Approved
0.707	Intermediate Similarity	NPD32	Approved
0.707	Intermediate Similarity	NPD4035	Approved
0.707	Intermediate Similarity	NPD4037	Approved
0.707	Intermediate Similarity	NPD31	Approved
0.707	Intermediate Similarity	NPD4033	Approved
0.707	Intermediate Similarity	NPD4122	Approved
0.707	Intermediate Similarity	NPD4034	Approved
0.707	Intermediate Similarity	NPD4036	Approved
0.707	Intermediate Similarity	NPD4039	Approved
0.7059	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5833	Phase 1
0.704	Intermediate Similarity	NPD3763	Approved
0.7033	Intermediate Similarity	NPD6569	Phase 2
0.7031	Intermediate Similarity	NPD1505	Phase 2
0.7025	Intermediate Similarity	NPD7955	Approved
0.7025	Intermediate Similarity	NPD7956	Approved
0.7017	Intermediate Similarity	NPD6243	Phase 3
0.7017	Intermediate Similarity	NPD6244	Phase 3
0.7014	Intermediate Similarity	NPD3477	Phase 2
0.7014	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4927	Discontinued
0.6983	Remote Similarity	NPD4454	Phase 2
0.6968	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5905	Phase 1
0.6964	Remote Similarity	NPD6974	Phase 3
0.6962	Remote Similarity	NPD8359	Phase 2
0.6957	Remote Similarity	NPD6962	Phase 2
0.6955	Remote Similarity	NPD6220	Phase 3
0.6955	Remote Similarity	NPD5939	Approved
0.6955	Remote Similarity	NPD5936	Approved
0.6936	Remote Similarity	NPD7417	Discontinued
0.6933	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7069	Discontinued
0.692	Remote Similarity	NPD5632	Approved
0.6913	Remote Similarity	NPD5022	Discontinued
0.6907	Remote Similarity	NPD6716	Phase 1
0.6901	Remote Similarity	NPD4604	Approved
0.6901	Remote Similarity	NPD4605	Approved
0.6901	Remote Similarity	NPD1229	Phase 2
0.6889	Remote Similarity	NPD2899	Discontinued
0.6889	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7719	Discontinued
0.6883	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7803	Approved
0.6883	Remote Similarity	NPD4996	Approved
0.6883	Remote Similarity	NPD4995	Approved
0.6878	Remote Similarity	NPD4206	Approved
0.6872	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD1856	Discontinued
0.6872	Remote Similarity	NPD1954	Phase 1
0.6866	Remote Similarity	NPD6669	Phase 2
0.6863	Remote Similarity	NPD6159	Phase 2
0.6861	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2564	Approved
0.6857	Remote Similarity	NPD2565	Phase 2
0.6844	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD7395	Discontinued
0.6842	Remote Similarity	NPD1034	Phase 3
0.6842	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.684	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.684	Remote Similarity	NPD4551	Phase 2
0.684	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.684	Remote Similarity	NPD4925	Approved
0.6838	Remote Similarity	NPD3006	Discontinued
0.6833	Remote Similarity	NPD3886	Phase 1
0.683	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6298	Discontinued
0.6824	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5066	Phase 2
0.6802	Remote Similarity	NPD5067	Phase 2
0.6787	Remote Similarity	NPD4437	Phase 3
0.6786	Remote Similarity	NPD4675	Approved
0.6786	Remote Similarity	NPD4678	Approved
0.6786	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7426	Phase 1
0.6783	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7674	Phase 3
0.6783	Remote Similarity	NPD7675	Phase 3
0.6783	Remote Similarity	NPD5640	Discontinued
0.6776	Remote Similarity	NPD5582	Discontinued
0.6765	Remote Similarity	NPD6517	Phase 3
0.6763	Remote Similarity	NPD3037	Phase 1
0.6761	Remote Similarity	NPD1038	Approved
0.6761	Remote Similarity	NPD6361	Phase 2
0.6759	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD4795	Phase 2
0.6757	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5645	Phase 3
0.6749	Remote Similarity	NPD4083	Discontinued
0.6746	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD5945	Phase 1
0.6741	Remote Similarity	NPD5944	Phase 1
0.6739	Remote Similarity	NPD6246	Approved
0.6739	Remote Similarity	NPD3925	Approved
0.6735	Remote Similarity	NPD8255	Phase 2
0.6735	Remote Similarity	NPD8244	Phase 2
0.6729	Remote Similarity	NPD3396	Approved
0.6729	Remote Similarity	NPD3395	Approved
0.6728	Remote Similarity	NPD1739	Approved
0.6728	Remote Similarity	NPD1740	Approved
0.6728	Remote Similarity	NPD6219	Discontinued
0.6727	Remote Similarity	NPD5530	Phase 1
0.6726	Remote Similarity	NPD5416	Discontinued
0.6726	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD3328	Phase 2
0.6721	Remote Similarity	NPD7708	Approved
0.6714	Remote Similarity	NPD3633	Approved
0.6714	Remote Similarity	NPD3634	Approved
0.6712	Remote Similarity	NPD6324	Phase 1
0.6701	Remote Similarity	NPD4123	Phase 3
0.6697	Remote Similarity	NPD7263	Phase 2
0.6683	Remote Similarity	NPD3386	Phase 2
0.6682	Remote Similarity	NPD2383	Phase 1
0.6682	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD4858	Phase 2
0.6681	Remote Similarity	NPD6643	Discontinued
0.6681	Remote Similarity	NPD4080	Discontinued
0.6667	Remote Similarity	NPD2779	Approved
0.6667	Remote Similarity	NPD8364	Approved
0.6667	Remote Similarity	NPD5805	Approved
0.6667	Remote Similarity	NPD2476	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8363	Approved
0.6667	Remote Similarity	NPD5482	Discontinued
0.6667	Remote Similarity	NPD5003	Discontinued
0.6653	Remote Similarity	NPD5539	Phase 2
0.6652	Remote Similarity	NPD6736	Discontinued
0.6651	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6251	Discontinued
0.665	Remote Similarity	NPD112	Approved
0.665	Remote Similarity	NPD9705	Discontinued

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