NPASS Compound

Structure

NPC68328 OpenBabel07101719132D 24 27 0 0 1 0 0 0 0 0999 V2000 -2.5981 0.5000 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 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 3.4641 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 2.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3735 2.7930 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 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 0.8660 0.5000 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 -0.7366 3.2272 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2395 3.2930 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 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 10 2 0 0 0 0 7 11 2 0 0 0 0 8 10 1 0 0 0 0 9 12 1 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 11 16 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 8 1 6 0 0 0 13 15 1 0 0 0 0 13 20 1 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 16 18 2 0 0 0 0 17 19 2 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	325.13
Volume:	330.657
LogP:	2.341
LogD:	2.487
LogS:	-2.793
# Rotatable Bonds:	3
TPSA:	56.79
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.942
Synthetic Accessibility Score:	3.184
Fsp3:	0.316
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:	-4.736
MDCK Permeability:	2.1259556888253428e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.11
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.765
Plasma Protein Binding (PPB):	93.72392272949219%
Volume Distribution (VD):	0.79
Pgp-substrate:	6.0777177810668945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.176
CYP1A2-substrate:	0.924
CYP2C19-inhibitor:	0.642
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.488
CYP2C9-substrate:	0.878
CYP2D6-inhibitor:	0.091
CYP2D6-substrate:	0.299
CYP3A4-inhibitor:	0.753
CYP3A4-substrate:	0.91

ADMET: Excretion

Clearance (CL):	2.854
Half-life (T1/2):	0.396

ADMET: Toxicity

hERG Blockers:	0.073
Human Hepatotoxicity (H-HT):	0.592
Drug-inuced Liver Injury (DILI):	0.881
AMES Toxicity:	0.329
Rat Oral Acute Toxicity:	0.392
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.13
Carcinogencity:	0.084
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.15

Download Data

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

Natural Product: NPC68328

Natural Product ID:	NPC68328
*Common Name:**	1,2,3-Trimethoxy-5-Oxonoraporphine
IUPAC Name:	(6aR)-1,2,3-trimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-5-one
Synonyms:
Standard InCHIKey:	YQESNKYPMKIBFJ-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C19H19NO4/c1-22-17-12-9-14(21)20-13-8-10-6-4-5-7-11(10)16(15(12)13)18(23-2)19(17)24-3/h4-7,13H,8-9H2,1-3H3,(H,20,21)/t13-/m1/s1
SMILES:	COc1c(OC)c2c3ccccc3C[C@@H]3c2c(c1OC)CC(=N3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491156
PubChem CID:	10853492
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO32498	Mitrephora maingayi	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479326]

☑ 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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	>	30.0	mg/ml	PMID[459591]

☑ 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 NPC68328 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	327
0.1-0.2	1605
0.2-0.3	7420
0.3-0.4	10681
0.4-0.5	5295
0.5-0.6	10208
0.6-0.7	5789
0.7-0.8	1211
0.8-0.85	133
0.85-0.9	26
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9745	High Similarity	NPC231371
0.875	High Similarity	NPC195766
0.875	High Similarity	NPC206736
0.8727	High Similarity	NPC118274
0.8727	High Similarity	NPC168753
0.8696	High Similarity	NPC329837
0.8675	High Similarity	NPC239775
0.8623	High Similarity	NPC474051
0.8608	High Similarity	NPC265473
0.8608	High Similarity	NPC276665
0.8529	High Similarity	NPC474507
0.8521	High Similarity	NPC148709
0.8521	High Similarity	NPC476577
0.8521	High Similarity	NPC173416
0.8519	High Similarity	NPC476572
0.8494	Intermediate Similarity	NPC474931
0.8494	Intermediate Similarity	NPC306555
0.8494	Intermediate Similarity	NPC145832
0.8494	Intermediate Similarity	NPC12053
0.8494	Intermediate Similarity	NPC158376
0.8494	Intermediate Similarity	NPC81218
0.8494	Intermediate Similarity	NPC117188
0.8494	Intermediate Similarity	NPC205421
0.8494	Intermediate Similarity	NPC204947
0.843	Intermediate Similarity	NPC276060
0.8395	Intermediate Similarity	NPC99659
0.8395	Intermediate Similarity	NPC325871
0.8373	Intermediate Similarity	NPC306843
0.8373	Intermediate Similarity	NPC253043
0.8373	Intermediate Similarity	NPC196447
0.8373	Intermediate Similarity	NPC96603
0.8373	Intermediate Similarity	NPC212794
0.8373	Intermediate Similarity	NPC477563
0.8373	Intermediate Similarity	NPC78222
0.8373	Intermediate Similarity	NPC136508
0.8373	Intermediate Similarity	NPC13504
0.8343	Intermediate Similarity	NPC19520
0.8343	Intermediate Similarity	NPC149090
0.8333	Intermediate Similarity	NPC219170
0.8333	Intermediate Similarity	NPC180253
0.8313	Intermediate Similarity	NPC324144
0.8313	Intermediate Similarity	NPC1229
0.8294	Intermediate Similarity	NPC66341
0.8294	Intermediate Similarity	NPC477020
0.8294	Intermediate Similarity	NPC192135
0.8286	Intermediate Similarity	NPC22928
0.8286	Intermediate Similarity	NPC57036
0.8286	Intermediate Similarity	NPC214116
0.8272	Intermediate Similarity	NPC275027
0.8266	Intermediate Similarity	NPC32413
0.8266	Intermediate Similarity	NPC474506
0.821	Intermediate Similarity	NPC81733
0.821	Intermediate Similarity	NPC326316
0.8208	Intermediate Similarity	NPC470879
0.8208	Intermediate Similarity	NPC258695
0.8198	Intermediate Similarity	NPC112575
0.8193	Intermediate Similarity	NPC166014
0.8193	Intermediate Similarity	NPC27410
0.8176	Intermediate Similarity	NPC26240
0.8176	Intermediate Similarity	NPC69712
0.8176	Intermediate Similarity	NPC477562
0.8166	Intermediate Similarity	NPC247389
0.8161	Intermediate Similarity	NPC195538
0.815	Intermediate Similarity	NPC320223
0.815	Intermediate Similarity	NPC114364
0.815	Intermediate Similarity	NPC23219
0.8146	Intermediate Similarity	NPC318805
0.8146	Intermediate Similarity	NPC41122
0.8144	Intermediate Similarity	NPC79402
0.8144	Intermediate Similarity	NPC80759
0.8136	Intermediate Similarity	NPC186546
0.8136	Intermediate Similarity	NPC476576
0.8114	Intermediate Similarity	NPC476202
0.8107	Intermediate Similarity	NPC476432
0.8107	Intermediate Similarity	NPC264850
0.8107	Intermediate Similarity	NPC24264
0.8107	Intermediate Similarity	NPC13916
0.8107	Intermediate Similarity	NPC219341
0.8101	Intermediate Similarity	NPC478093
0.8101	Intermediate Similarity	NPC117717
0.809	Intermediate Similarity	NPC82763
0.8084	Intermediate Similarity	NPC230956
0.8084	Intermediate Similarity	NPC271388
0.8084	Intermediate Similarity	NPC205255
0.8084	Intermediate Similarity	NPC235143
0.8084	Intermediate Similarity	NPC119649
0.8068	Intermediate Similarity	NPC302275
0.8066	Intermediate Similarity	NPC234318
0.8056	Intermediate Similarity	NPC478092
0.8056	Intermediate Similarity	NPC478091
0.8056	Intermediate Similarity	NPC30182
0.8056	Intermediate Similarity	NPC473589
0.8056	Intermediate Similarity	NPC85381
0.8049	Intermediate Similarity	NPC114124
0.8047	Intermediate Similarity	NPC24465
0.8047	Intermediate Similarity	NPC302527
0.8047	Intermediate Similarity	NPC16805
0.8047	Intermediate Similarity	NPC225774
0.8047	Intermediate Similarity	NPC167546
0.8046	Intermediate Similarity	NPC260118
0.8035	Intermediate Similarity	NPC128560
0.8035	Intermediate Similarity	NPC199465
0.8035	Intermediate Similarity	NPC229166
0.8024	Intermediate Similarity	NPC221864
0.8023	Intermediate Similarity	NPC249996
0.8023	Intermediate Similarity	NPC95426
0.8023	Intermediate Similarity	NPC302245
0.8023	Intermediate Similarity	NPC16357
0.8012	Intermediate Similarity	NPC126519
0.8012	Intermediate Similarity	NPC203784
0.8012	Intermediate Similarity	NPC170503
0.8011	Intermediate Similarity	NPC248642
0.8	Intermediate Similarity	NPC35627
0.8	Intermediate Similarity	NPC215747
0.8	Intermediate Similarity	NPC476573
0.8	Intermediate Similarity	NPC81247
0.8	Intermediate Similarity	NPC192939
0.7989	Intermediate Similarity	NPC265383
0.7988	Intermediate Similarity	NPC52475
0.7988	Intermediate Similarity	NPC127402
0.7978	Intermediate Similarity	NPC139783
0.7978	Intermediate Similarity	NPC14507
0.7978	Intermediate Similarity	NPC47077
0.7978	Intermediate Similarity	NPC65312
0.7966	Intermediate Similarity	NPC156576
0.7966	Intermediate Similarity	NPC135772
0.7956	Intermediate Similarity	NPC29472
0.7953	Intermediate Similarity	NPC210918
0.7953	Intermediate Similarity	NPC298979
0.7952	Intermediate Similarity	NPC107602
0.7952	Intermediate Similarity	NPC123323
0.7944	Intermediate Similarity	NPC294244
0.7939	Intermediate Similarity	NPC18614
0.7933	Intermediate Similarity	NPC275680
0.7933	Intermediate Similarity	NPC22115
0.7929	Intermediate Similarity	NPC60186
0.7911	Intermediate Similarity	NPC266006
0.791	Intermediate Similarity	NPC28425
0.7907	Intermediate Similarity	NPC182257
0.7907	Intermediate Similarity	NPC83198
0.7907	Intermediate Similarity	NPC204908
0.7901	Intermediate Similarity	NPC476565
0.7898	Intermediate Similarity	NPC126284
0.7895	Intermediate Similarity	NPC223077
0.7895	Intermediate Similarity	NPC56887
0.7895	Intermediate Similarity	NPC193853
0.7874	Intermediate Similarity	NPC190783
0.7874	Intermediate Similarity	NPC228040
0.7874	Intermediate Similarity	NPC152680
0.7874	Intermediate Similarity	NPC232386
0.787	Intermediate Similarity	NPC306902
0.787	Intermediate Similarity	NPC477559
0.787	Intermediate Similarity	NPC266753
0.787	Intermediate Similarity	NPC232924
0.787	Intermediate Similarity	NPC160298
0.7861	Intermediate Similarity	NPC6152
0.7853	Intermediate Similarity	NPC155442
0.7853	Intermediate Similarity	NPC119579
0.7853	Intermediate Similarity	NPC477561
0.7853	Intermediate Similarity	NPC476574
0.7853	Intermediate Similarity	NPC312918
0.7848	Intermediate Similarity	NPC205442
0.7848	Intermediate Similarity	NPC202846
0.7848	Intermediate Similarity	NPC143139
0.7845	Intermediate Similarity	NPC475754
0.7845	Intermediate Similarity	NPC259350
0.7845	Intermediate Similarity	NPC223236
0.7844	Intermediate Similarity	NPC244112
0.7836	Intermediate Similarity	NPC209377
0.7829	Intermediate Similarity	NPC477558
0.7812	Intermediate Similarity	NPC308768
0.7812	Intermediate Similarity	NPC12668
0.7811	Intermediate Similarity	NPC7393
0.7809	Intermediate Similarity	NPC116284
0.7799	Intermediate Similarity	NPC296898
0.7799	Intermediate Similarity	NPC242715
0.7799	Intermediate Similarity	NPC56329
0.7797	Intermediate Similarity	NPC311936
0.7785	Intermediate Similarity	NPC200557
0.7785	Intermediate Similarity	NPC158142
0.7785	Intermediate Similarity	NPC241241
0.7785	Intermediate Similarity	NPC10314
0.7785	Intermediate Similarity	NPC294884
0.7785	Intermediate Similarity	NPC108198
0.7785	Intermediate Similarity	NPC69029
0.7784	Intermediate Similarity	NPC226941
0.7784	Intermediate Similarity	NPC108957
0.7784	Intermediate Similarity	NPC14005
0.7778	Intermediate Similarity	NPC474009
0.7771	Intermediate Similarity	NPC476568
0.7771	Intermediate Similarity	NPC289743
0.7771	Intermediate Similarity	NPC110374
0.776	Intermediate Similarity	NPC256124
0.7756	Intermediate Similarity	NPC149337
0.7756	Intermediate Similarity	NPC471983
0.7753	Intermediate Similarity	NPC286119
0.775	Intermediate Similarity	NPC105847
0.775	Intermediate Similarity	NPC218131
0.775	Intermediate Similarity	NPC220344
0.775	Intermediate Similarity	NPC243759

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 NPC68328 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	782
0.2-0.3	1012
0.3-0.4	2250
0.4-0.5	2596
0.5-0.6	1647
0.6-0.7	547
0.7-0.8	107
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8528	High Similarity	NPD4055	Discovery
0.8438	Intermediate Similarity	NPD4005	Discontinued
0.7976	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD5090	Approved
0.7784	Intermediate Similarity	NPD5089	Approved
0.7778	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD4678	Approved
0.7725	Intermediate Similarity	NPD4675	Approved
0.7716	Intermediate Similarity	NPD6331	Phase 2
0.7714	Intermediate Similarity	NPD8099	Discontinued
0.7714	Intermediate Similarity	NPD8251	Approved
0.7714	Intermediate Similarity	NPD8252	Approved
0.7709	Intermediate Similarity	NPD8053	Approved
0.7709	Intermediate Similarity	NPD8054	Approved
0.7688	Intermediate Similarity	NPD3051	Approved
0.767	Intermediate Similarity	NPD8156	Discontinued
0.7636	Intermediate Similarity	NPD4584	Approved
0.7607	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6788	Approved
0.7593	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7906	Approved
0.7561	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD2970	Approved
0.7543	Intermediate Similarity	NPD2969	Approved
0.7532	Intermediate Similarity	NPD2674	Phase 3
0.747	Intermediate Similarity	NPD2420	Approved
0.747	Intermediate Similarity	NPD2421	Approved
0.7468	Intermediate Similarity	NPD1669	Approved
0.7459	Intermediate Similarity	NPD4578	Approved
0.7459	Intermediate Similarity	NPD4577	Approved
0.7458	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5241	Discontinued
0.7432	Intermediate Similarity	NPD4663	Approved
0.7425	Intermediate Similarity	NPD4123	Phase 3
0.7416	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD27	Approved
0.7401	Intermediate Similarity	NPD2489	Approved
0.7386	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7313	Approved
0.7363	Intermediate Similarity	NPD7311	Approved
0.7363	Intermediate Similarity	NPD7310	Approved
0.7363	Intermediate Similarity	NPD7312	Approved
0.7358	Intermediate Similarity	NPD3145	Approved
0.7358	Intermediate Similarity	NPD3144	Approved
0.7353	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7309	Approved
0.7312	Intermediate Similarity	NPD7477	Discontinued
0.7303	Intermediate Similarity	NPD4481	Phase 3
0.7299	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6746	Phase 2
0.7222	Intermediate Similarity	NPD7827	Phase 1
0.7211	Intermediate Similarity	NPD2974	Approved
0.7211	Intermediate Similarity	NPD2973	Approved
0.7211	Intermediate Similarity	NPD2975	Approved
0.7202	Intermediate Similarity	NPD7124	Phase 2
0.7195	Intermediate Similarity	NPD4108	Discontinued
0.7188	Intermediate Similarity	NPD1024	Discontinued
0.7176	Intermediate Similarity	NPD7526	Approved
0.7176	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD52	Approved
0.7169	Intermediate Similarity	NPD7153	Discontinued
0.7168	Intermediate Similarity	NPD6072	Discontinued
0.7168	Intermediate Similarity	NPD7438	Suspended
0.716	Intermediate Similarity	NPD4357	Discontinued
0.7159	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7833	Phase 2
0.7159	Intermediate Similarity	NPD7831	Phase 2
0.7152	Intermediate Similarity	NPD2161	Phase 2
0.7143	Intermediate Similarity	NPD2560	Approved
0.7143	Intermediate Similarity	NPD2563	Approved
0.7112	Intermediate Similarity	NPD6843	Phase 3
0.7112	Intermediate Similarity	NPD6841	Approved
0.7112	Intermediate Similarity	NPD6842	Approved
0.7098	Intermediate Similarity	NPD4580	Approved
0.7086	Intermediate Similarity	NPD5773	Approved
0.7086	Intermediate Similarity	NPD5772	Approved
0.7086	Intermediate Similarity	NPD4585	Approved
0.7081	Intermediate Similarity	NPD3027	Phase 3
0.7073	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD3452	Approved
0.7062	Intermediate Similarity	NPD3450	Approved
0.7062	Intermediate Similarity	NPD2493	Approved
0.7062	Intermediate Similarity	NPD2494	Approved
0.7055	Intermediate Similarity	NPD3110	Approved
0.7055	Intermediate Similarity	NPD3109	Approved
0.7052	Intermediate Similarity	NPD4017	Approved
0.7029	Intermediate Similarity	NPD7298	Approved
0.7027	Intermediate Similarity	NPD7549	Discontinued
0.7024	Intermediate Similarity	NPD5177	Phase 3
0.7018	Intermediate Similarity	NPD1424	Approved
0.7017	Intermediate Similarity	NPD2898	Approved
0.7006	Intermediate Similarity	NPD1375	Discontinued
0.7	Intermediate Similarity	NPD6071	Discontinued
0.6989	Remote Similarity	NPD2968	Approved
0.6989	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD2971	Approved
0.6975	Remote Similarity	NPD4625	Phase 3
0.6971	Remote Similarity	NPD4772	Phase 2
0.6971	Remote Similarity	NPD4773	Phase 2
0.697	Remote Similarity	NPD4097	Suspended
0.697	Remote Similarity	NPD2157	Approved
0.6959	Remote Similarity	NPD8095	Phase 1
0.6954	Remote Similarity	NPD4583	Approved
0.6954	Remote Similarity	NPD4582	Approved
0.6947	Remote Similarity	NPD2490	Approved
0.6947	Remote Similarity	NPD2488	Approved
0.6941	Remote Similarity	NPD2219	Phase 1
0.6941	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6031	Approved
0.6936	Remote Similarity	NPD6030	Approved
0.6933	Remote Similarity	NPD5109	Approved
0.6933	Remote Similarity	NPD5111	Phase 2
0.6933	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5110	Phase 2
0.6931	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7447	Phase 1
0.6918	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6502	Phase 2
0.6914	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6232	Discontinued
0.6906	Remote Similarity	NPD4010	Discontinued
0.6905	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD4004	Approved
0.6904	Remote Similarity	NPD4002	Approved
0.6901	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3845	Phase 1
0.6898	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4474	Approved
0.689	Remote Similarity	NPD4475	Approved
0.6886	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD3489	Phase 3
0.6879	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2922	Phase 1
0.6872	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD4083	Discontinued
0.686	Remote Similarity	NPD7212	Phase 2
0.686	Remote Similarity	NPD7213	Phase 3
0.6853	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3018	Phase 2
0.6848	Remote Similarity	NPD1613	Approved
0.6848	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD2238	Phase 2
0.6842	Remote Similarity	NPD3692	Discontinued
0.6839	Remote Similarity	NPD3639	Approved
0.6839	Remote Similarity	NPD2122	Discontinued
0.6839	Remote Similarity	NPD3640	Phase 3
0.6839	Remote Similarity	NPD3641	Approved
0.6836	Remote Similarity	NPD37	Approved
0.6826	Remote Similarity	NPD6111	Discontinued
0.6824	Remote Similarity	NPD3060	Approved
0.6824	Remote Similarity	NPD4237	Approved
0.6824	Remote Similarity	NPD6674	Discontinued
0.6824	Remote Similarity	NPD4236	Phase 3
0.6821	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4739	Approved
0.6818	Remote Similarity	NPD5617	Suspended
0.6811	Remote Similarity	NPD5844	Phase 1
0.6811	Remote Similarity	NPD42	Phase 2
0.6811	Remote Similarity	NPD6042	Phase 2
0.681	Remote Similarity	NPD4908	Phase 1
0.68	Remote Similarity	NPD2883	Discontinued
0.6796	Remote Similarity	NPD5677	Discontinued
0.6793	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7473	Discontinued
0.6788	Remote Similarity	NPD839	Approved
0.6788	Remote Similarity	NPD840	Approved
0.6788	Remote Similarity	NPD7125	Discontinued
0.6782	Remote Similarity	NPD1351	Approved
0.6782	Remote Similarity	NPD1350	Approved
0.6782	Remote Similarity	NPD1349	Approved
0.6782	Remote Similarity	NPD6090	Discontinued
0.678	Remote Similarity	NPD7047	Phase 3
0.678	Remote Similarity	NPD3778	Approved
0.678	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5604	Discontinued
0.6778	Remote Similarity	NPD8070	Approved
0.6776	Remote Similarity	NPD5242	Approved
0.6772	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5006	Approved
0.6768	Remote Similarity	NPD5005	Approved
0.6761	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7291	Discontinued
0.6751	Remote Similarity	NPD6612	Phase 2
0.6748	Remote Similarity	NPD1712	Approved
0.6743	Remote Similarity	NPD5976	Discontinued
0.674	Remote Similarity	NPD5709	Phase 3
0.6739	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7007	Discovery
0.6727	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5718	Phase 2
0.6726	Remote Similarity	NPD6896	Approved
0.6726	Remote Similarity	NPD6895	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