NPASS Compound

Structure

NPC203168 OpenBabel07101719122D 24 26 0 0 1 0 0 0 0 0999 V2000 -2.4538 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -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 2.6831 -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 0.9511 -1.3090 0.0000 C 0 0 0 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 0.0000 -1.6180 0.0000 C 0 0 1 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 -0.5878 -0.8090 0.0000 C 0 0 2 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 -0.3090 -2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 0.0570 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 21 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 6 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 17 1 6 0 0 0 15 24 1 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	335.14
Volume:	327.475
LogP:	2.168
LogD:	2.147
LogS:	-2.608
# Rotatable Bonds:	4
TPSA:	90.27
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.881
Synthetic Accessibility Score:	3.747
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:	-4.834
MDCK Permeability:	2.6656971385818906e-05
Pgp-inhibitor:	0.037
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.074
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.949
Plasma Protein Binding (PPB):	84.28498840332031%
Volume Distribution (VD):	1.09
Pgp-substrate:	15.956876754760742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.115
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.908
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.808
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.582
CYP3A4-inhibitor:	0.114
CYP3A4-substrate:	0.688

ADMET: Excretion

Clearance (CL):	6.554
Half-life (T1/2):	0.495

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.051
Drug-inuced Liver Injury (DILI):	0.49
AMES Toxicity:	0.074
Rat Oral Acute Toxicity:	0.331
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.077
Carcinogencity:	0.05
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.105

Download Data

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

Natural Product: NPC203168

Natural Product ID:	NPC203168
*Common Name:**	Cis-(+)-7,8-Dimethoxymyrtopsine
IUPAC Name:	(2R,3S)-2-(2-hydroxypropan-2-yl)-4,7,8-trimethoxy-2,3-dihydrofuro[2,3-b]quinolin-3-ol
Synonyms:
Standard InCHIKey:	UFSDNXBDTQSQFM-SWLSCSKDSA-N
Standard InCHI:	InChI=1S/C17H21NO6/c1-17(2,20)15-12(19)10-13(22-4)8-6-7-9(21-3)14(23-5)11(8)18-16(10)24-15/h6-7,12,15,19-20H,1-5H3/t12-,15+/m0/s1
SMILES:	COc1c2c(O[C@H]([C@H]2O)C(O)(C)C)nc2c1ccc(c2OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463651
PubChem CID:	16062333
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	=	85.4	%	PMID[538561]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	78.3	%	PMID[538561]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	79.0	%	PMID[538561]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	89.4	%	PMID[538561]

☑ 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 NPC203168 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	2394
0.2-0.3	12514
0.3-0.4	5613
0.4-0.5	11487
0.5-0.6	8608
0.6-0.7	1330
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	NPC219664
0.9215	High Similarity	NPC66815
0.8698	High Similarity	NPC279401
0.8698	High Similarity	NPC79293
0.8618	High Similarity	NPC58209
0.8365	Intermediate Similarity	NPC148409
0.8356	Intermediate Similarity	NPC160100
0.8311	Intermediate Similarity	NPC166712
0.8302	Intermediate Similarity	NPC200888
0.8276	Intermediate Similarity	NPC474595
0.8213	Intermediate Similarity	NPC474594
0.8203	Intermediate Similarity	NPC34770
0.8144	Intermediate Similarity	NPC42591
0.8093	Intermediate Similarity	NPC62069
0.8056	Intermediate Similarity	NPC476997
0.8018	Intermediate Similarity	NPC476996
0.8018	Intermediate Similarity	NPC476998
0.7972	Intermediate Similarity	NPC476994
0.7961	Intermediate Similarity	NPC304183
0.7946	Intermediate Similarity	NPC188400
0.7946	Intermediate Similarity	NPC208364
0.793	Intermediate Similarity	NPC203373
0.7879	Intermediate Similarity	NPC66083
0.7847	Intermediate Similarity	NPC209769
0.7835	Intermediate Similarity	NPC283152
0.7826	Intermediate Similarity	NPC470930
0.7807	Intermediate Similarity	NPC173250
0.7784	Intermediate Similarity	NPC194724
0.7729	Intermediate Similarity	NPC199277
0.7729	Intermediate Similarity	NPC135887
0.7723	Intermediate Similarity	NPC476995
0.7721	Intermediate Similarity	NPC469594
0.7699	Intermediate Similarity	NPC101312
0.7678	Intermediate Similarity	NPC469589
0.7673	Intermediate Similarity	NPC469390
0.7658	Intermediate Similarity	NPC217176
0.765	Intermediate Similarity	NPC204385
0.7641	Intermediate Similarity	NPC312872
0.7639	Intermediate Similarity	NPC473822
0.7634	Intermediate Similarity	NPC277351
0.7607	Intermediate Similarity	NPC120513
0.7602	Intermediate Similarity	NPC288943
0.7593	Intermediate Similarity	NPC314552
0.7585	Intermediate Similarity	NPC128823
0.7578	Intermediate Similarity	NPC476999
0.7571	Intermediate Similarity	NPC164374
0.7571	Intermediate Similarity	NPC137929
0.7552	Intermediate Similarity	NPC118511
0.7545	Intermediate Similarity	NPC205372
0.7536	Intermediate Similarity	NPC476106
0.7536	Intermediate Similarity	NPC471736
0.7535	Intermediate Similarity	NPC471080
0.7535	Intermediate Similarity	NPC469592
0.7523	Intermediate Similarity	NPC140296
0.7511	Intermediate Similarity	NPC473182
0.7489	Intermediate Similarity	NPC473183
0.7477	Intermediate Similarity	NPC131885
0.7477	Intermediate Similarity	NPC173080
0.7475	Intermediate Similarity	NPC61350
0.7465	Intermediate Similarity	NPC288349
0.7453	Intermediate Similarity	NPC472111
0.745	Intermediate Similarity	NPC206201
0.7432	Intermediate Similarity	NPC97746
0.7424	Intermediate Similarity	NPC168922
0.7407	Intermediate Similarity	NPC26679
0.7401	Intermediate Similarity	NPC473184
0.7385	Intermediate Similarity	NPC8022
0.7385	Intermediate Similarity	NPC470799
0.7383	Intermediate Similarity	NPC470931
0.7383	Intermediate Similarity	NPC308392
0.7376	Intermediate Similarity	NPC320394
0.7364	Intermediate Similarity	NPC473179
0.7363	Intermediate Similarity	NPC474798
0.7358	Intermediate Similarity	NPC469440
0.7346	Intermediate Similarity	NPC470586
0.7345	Intermediate Similarity	NPC201508
0.7343	Intermediate Similarity	NPC475190
0.733	Intermediate Similarity	NPC174049
0.7328	Intermediate Similarity	NPC291609
0.7327	Intermediate Similarity	NPC316981
0.7327	Intermediate Similarity	NPC112206
0.7327	Intermediate Similarity	NPC202605
0.7317	Intermediate Similarity	NPC110741
0.7313	Intermediate Similarity	NPC478032
0.7311	Intermediate Similarity	NPC291535
0.7311	Intermediate Similarity	NPC475085
0.7311	Intermediate Similarity	NPC475112
0.7308	Intermediate Similarity	NPC472068
0.7294	Intermediate Similarity	NPC162530
0.7288	Intermediate Similarity	NPC473188
0.7285	Intermediate Similarity	NPC298436
0.7284	Intermediate Similarity	NPC124300
0.7281	Intermediate Similarity	NPC255800
0.7281	Intermediate Similarity	NPC96584
0.7277	Intermediate Similarity	NPC162484
0.7269	Intermediate Similarity	NPC185782
0.7265	Intermediate Similarity	NPC122463
0.7265	Intermediate Similarity	NPC118121
0.7264	Intermediate Similarity	NPC31930
0.7248	Intermediate Similarity	NPC48353
0.7244	Intermediate Similarity	NPC202503
0.724	Intermediate Similarity	NPC204446
0.7238	Intermediate Similarity	NPC243834
0.7238	Intermediate Similarity	NPC70956
0.7234	Intermediate Similarity	NPC1608
0.7215	Intermediate Similarity	NPC266931
0.7212	Intermediate Similarity	NPC195268
0.7212	Intermediate Similarity	NPC141915
0.7212	Intermediate Similarity	NPC114335
0.7212	Intermediate Similarity	NPC473185
0.7212	Intermediate Similarity	NPC280964
0.7212	Intermediate Similarity	NPC133140
0.7204	Intermediate Similarity	NPC72211
0.7196	Intermediate Similarity	NPC475774
0.7195	Intermediate Similarity	NPC473513
0.7192	Intermediate Similarity	NPC118776
0.7191	Intermediate Similarity	NPC310618
0.719	Intermediate Similarity	NPC473053
0.7188	Intermediate Similarity	NPC26872
0.7178	Intermediate Similarity	NPC472168
0.7176	Intermediate Similarity	NPC193777
0.7175	Intermediate Similarity	NPC132642
0.7167	Intermediate Similarity	NPC99891
0.7167	Intermediate Similarity	NPC475844
0.7163	Intermediate Similarity	NPC118832
0.7163	Intermediate Similarity	NPC329708
0.7163	Intermediate Similarity	NPC165349
0.7163	Intermediate Similarity	NPC264166
0.7163	Intermediate Similarity	NPC274291
0.7163	Intermediate Similarity	NPC47059
0.7163	Intermediate Similarity	NPC16452
0.7163	Intermediate Similarity	NPC36229
0.7163	Intermediate Similarity	NPC476581
0.715	Intermediate Similarity	NPC242928
0.7143	Intermediate Similarity	NPC475910
0.7136	Intermediate Similarity	NPC234197
0.7136	Intermediate Similarity	NPC11017
0.7118	Intermediate Similarity	NPC475253
0.7116	Intermediate Similarity	NPC223427
0.7109	Intermediate Similarity	NPC70259
0.7107	Intermediate Similarity	NPC129897
0.7104	Intermediate Similarity	NPC235076
0.7101	Intermediate Similarity	NPC472066
0.7101	Intermediate Similarity	NPC472031
0.7101	Intermediate Similarity	NPC472067
0.7091	Intermediate Similarity	NPC53069
0.7091	Intermediate Similarity	NPC202768
0.7091	Intermediate Similarity	NPC296482
0.709	Intermediate Similarity	NPC209981
0.7089	Intermediate Similarity	NPC476578
0.7089	Intermediate Similarity	NPC476582
0.7089	Intermediate Similarity	NPC4071
0.7087	Intermediate Similarity	NPC62510
0.7085	Intermediate Similarity	NPC23614
0.7085	Intermediate Similarity	NPC100079
0.7078	Intermediate Similarity	NPC188420
0.7077	Intermediate Similarity	NPC26850
0.7076	Intermediate Similarity	NPC284141
0.7076	Intermediate Similarity	NPC472434
0.7075	Intermediate Similarity	NPC272706
0.7075	Intermediate Similarity	NPC224928
0.7074	Intermediate Similarity	NPC469792
0.7073	Intermediate Similarity	NPC227824
0.7067	Intermediate Similarity	NPC477532
0.7062	Intermediate Similarity	NPC43787
0.7062	Intermediate Similarity	NPC131017
0.7062	Intermediate Similarity	NPC205934
0.7061	Intermediate Similarity	NPC110151
0.7059	Intermediate Similarity	NPC271215
0.7059	Intermediate Similarity	NPC149471
0.7053	Intermediate Similarity	NPC314573
0.7048	Intermediate Similarity	NPC179287
0.7048	Intermediate Similarity	NPC294244
0.7039	Intermediate Similarity	NPC84478
0.7035	Intermediate Similarity	NPC280272
0.7032	Intermediate Similarity	NPC201697
0.7031	Intermediate Similarity	NPC252251
0.7023	Intermediate Similarity	NPC267423
0.7022	Intermediate Similarity	NPC128115
0.7022	Intermediate Similarity	NPC54066
0.7018	Intermediate Similarity	NPC313189
0.7015	Intermediate Similarity	NPC252590
0.7014	Intermediate Similarity	NPC226202
0.7013	Intermediate Similarity	NPC469554
0.7009	Intermediate Similarity	NPC474183
0.7009	Intermediate Similarity	NPC470784
0.7009	Intermediate Similarity	NPC470785
0.6979	Remote Similarity	NPC41501
0.6978	Remote Similarity	NPC208084
0.6978	Remote Similarity	NPC46451
0.6977	Remote Similarity	NPC477019
0.6974	Remote Similarity	NPC473449
0.697	Remote Similarity	NPC477531
0.6968	Remote Similarity	NPC146418
0.6967	Remote Similarity	NPC284685
0.6966	Remote Similarity	NPC184680
0.6959	Remote Similarity	NPC153769
0.6957	Remote Similarity	NPC274640
0.6951	Remote Similarity	NPC16066
0.6949	Remote Similarity	NPC217554

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 NPC203168 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	661
0.2-0.3	1065
0.3-0.4	1952
0.4-0.5	2791
0.5-0.6	1777
0.6-0.7	553
0.7-0.8	42
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
0.8	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6494	Phase 2
0.7746	Intermediate Similarity	NPD5903	Approved
0.7746	Intermediate Similarity	NPD5902	Approved
0.7606	Intermediate Similarity	NPD4502	Phase 2
0.7602	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD5164	Discontinued
0.7583	Intermediate Similarity	NPD7222	Phase 2
0.7562	Intermediate Similarity	NPD5256	Discontinued
0.7536	Intermediate Similarity	NPD3003	Approved
0.7525	Intermediate Similarity	NPD3920	Phase 2
0.7523	Intermediate Similarity	NPD3875	Discontinued
0.7511	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD7558	Phase 2
0.75	Intermediate Similarity	NPD1768	Approved
0.7465	Intermediate Similarity	NPD5658	Approved
0.745	Intermediate Similarity	NPD4204	Approved
0.745	Intermediate Similarity	NPD4203	Approved
0.744	Intermediate Similarity	NPD6550	Discontinued
0.7418	Intermediate Similarity	NPD7452	Approved
0.7418	Intermediate Similarity	NPD7453	Approved
0.7398	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6590	Discontinued
0.7348	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2176	Approved
0.7333	Intermediate Similarity	NPD2175	Phase 3
0.7333	Intermediate Similarity	NPD2177	Approved
0.729	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD4131	Phase 3
0.7273	Intermediate Similarity	NPD5512	Phase 3
0.7256	Intermediate Similarity	NPD1392	Approved
0.7252	Intermediate Similarity	NPD5930	Phase 3
0.724	Intermediate Similarity	NPD6985	Discontinued
0.7227	Intermediate Similarity	NPD5612	Discontinued
0.7212	Intermediate Similarity	NPD3924	Approved
0.7212	Intermediate Similarity	NPD3923	Approved
0.7212	Intermediate Similarity	NPD3921	Approved
0.7212	Intermediate Similarity	NPD3922	Approved
0.7207	Intermediate Similarity	NPD7194	Discontinued
0.7185	Intermediate Similarity	NPD7859	Phase 2
0.7176	Intermediate Similarity	NPD6290	Phase 2
0.7163	Intermediate Similarity	NPD32	Approved
0.7163	Intermediate Similarity	NPD4038	Approved
0.7163	Intermediate Similarity	NPD4035	Approved
0.7163	Intermediate Similarity	NPD4122	Approved
0.7163	Intermediate Similarity	NPD4033	Approved
0.7163	Intermediate Similarity	NPD31	Approved
0.7163	Intermediate Similarity	NPD4036	Approved
0.7163	Intermediate Similarity	NPD4037	Approved
0.7163	Intermediate Similarity	NPD4039	Approved
0.7163	Intermediate Similarity	NPD4034	Approved
0.7143	Intermediate Similarity	NPD4418	Discontinued
0.7143	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD4875	Phase 3
0.7137	Intermediate Similarity	NPD4876	Phase 3
0.7137	Intermediate Similarity	NPD7169	Suspended
0.713	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6964	Approved
0.71	Intermediate Similarity	NPD6963	Approved
0.7097	Intermediate Similarity	NPD5429	Discontinued
0.7095	Intermediate Similarity	NPD7125	Discontinued
0.7091	Intermediate Similarity	NPD3815	Phase 1
0.7091	Intermediate Similarity	NPD3816	Phase 1
0.7075	Intermediate Similarity	NPD6988	Phase 1
0.7072	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD4454	Phase 2
0.7064	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5939	Approved
0.7045	Intermediate Similarity	NPD5936	Approved
0.7043	Intermediate Similarity	NPD1505	Phase 2
0.7033	Intermediate Similarity	NPD2845	Phase 2
0.7033	Intermediate Similarity	NPD2843	Phase 2
0.7027	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4604	Approved
0.6995	Remote Similarity	NPD4605	Approved
0.6992	Remote Similarity	NPD5833	Phase 1
0.6981	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3763	Approved
0.6967	Remote Similarity	NPD7955	Approved
0.6967	Remote Similarity	NPD6569	Phase 2
0.6967	Remote Similarity	NPD7956	Approved
0.6958	Remote Similarity	NPD6244	Phase 3
0.6958	Remote Similarity	NPD6243	Phase 3
0.6949	Remote Similarity	NPD7417	Discontinued
0.6948	Remote Similarity	NPD3477	Phase 2
0.6948	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4927	Discontinued
0.6933	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD5022	Discontinued
0.692	Remote Similarity	NPD6716	Phase 1
0.6916	Remote Similarity	NPD1229	Phase 2
0.6907	Remote Similarity	NPD5905	Phase 1
0.6906	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD8359	Phase 2
0.6903	Remote Similarity	NPD6974	Phase 3
0.6903	Remote Similarity	NPD2899	Discontinued
0.6897	Remote Similarity	NPD6962	Phase 2
0.6892	Remote Similarity	NPD6220	Phase 3
0.6886	Remote Similarity	NPD1856	Discontinued
0.6886	Remote Similarity	NPD1954	Phase 1
0.6881	Remote Similarity	NPD6669	Phase 2
0.6878	Remote Similarity	NPD6159	Phase 2
0.6872	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD7069	Discontinued
0.6858	Remote Similarity	NPD7395	Discontinued
0.6858	Remote Similarity	NPD5632	Approved
0.6854	Remote Similarity	NPD4551	Phase 2
0.6853	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD7803	Approved
0.6826	Remote Similarity	NPD7719	Discontinued
0.6824	Remote Similarity	NPD4995	Approved
0.6824	Remote Similarity	NPD4996	Approved
0.6824	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD5067	Phase 2
0.6816	Remote Similarity	NPD8244	Phase 2
0.6816	Remote Similarity	NPD5066	Phase 2
0.6816	Remote Similarity	NPD4206	Approved
0.6812	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4675	Approved
0.6802	Remote Similarity	NPD4678	Approved
0.6802	Remote Similarity	NPD4437	Phase 3
0.68	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7675	Phase 3
0.6797	Remote Similarity	NPD7426	Phase 1
0.6797	Remote Similarity	NPD5640	Discontinued
0.6797	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7674	Phase 3
0.6792	Remote Similarity	NPD2565	Phase 2
0.6792	Remote Similarity	NPD2564	Approved
0.6791	Remote Similarity	NPD5582	Discontinued
0.6781	Remote Similarity	NPD4925	Approved
0.678	Remote Similarity	NPD3006	Discontinued
0.6779	Remote Similarity	NPD3037	Phase 1
0.6778	Remote Similarity	NPD6517	Phase 3
0.6777	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD1034	Phase 3
0.6777	Remote Similarity	NPD2383	Phase 1
0.6777	Remote Similarity	NPD3886	Phase 1
0.6776	Remote Similarity	NPD6361	Phase 2
0.6771	Remote Similarity	NPD5645	Phase 3
0.6771	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6298	Discontinued
0.6766	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD4080	Discontinued
0.6765	Remote Similarity	NPD4083	Discontinued
0.6762	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD5944	Phase 1
0.6756	Remote Similarity	NPD5945	Phase 1
0.6753	Remote Similarity	NPD3925	Approved
0.6753	Remote Similarity	NPD6246	Approved
0.6742	Remote Similarity	NPD5530	Phase 1
0.6741	Remote Similarity	NPD5416	Discontinued
0.6741	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3328	Phase 2
0.673	Remote Similarity	NPD6339	Approved
0.673	Remote Similarity	NPD6340	Approved
0.6726	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD4123	Phase 3
0.6712	Remote Similarity	NPD7263	Phase 2
0.67	Remote Similarity	NPD5773	Approved
0.67	Remote Similarity	NPD5772	Approved
0.6698	Remote Similarity	NPD1038	Approved
0.6697	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4795	Phase 2
0.6682	Remote Similarity	NPD2476	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD5805	Approved
0.668	Remote Similarity	NPD8364	Approved
0.668	Remote Similarity	NPD8255	Phase 2
0.668	Remote Similarity	NPD8363	Approved
0.6667	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3395	Approved
0.6667	Remote Similarity	NPD6736	Discontinued
0.6667	Remote Similarity	NPD1740	Approved
0.6667	Remote Similarity	NPD1739	Approved
0.6667	Remote Similarity	NPD7708	Approved
0.6667	Remote Similarity	NPD3396	Approved
0.6667	Remote Similarity	NPD6219	Discontinued
0.6667	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD4349	Approved
0.6653	Remote Similarity	NPD4350	Approved
0.6653	Remote Similarity	NPD7796	Approved
0.6653	Remote Similarity	NPD7797	Approved
0.6652	Remote Similarity	NPD6991	Approved
0.6652	Remote Similarity	NPD6324	Phase 1
0.6652	Remote Similarity	NPD3263	Phase 3
0.6652	Remote Similarity	NPD4897	Phase 2
0.6651	Remote Similarity	NPD3634	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