NPASS Compound

Structure

NPC220961 OpenBabel07101718252D 28 31 0 0 1 0 0 0 0 0999 V2000 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4644 -0.4579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 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 -3.6285 1.3759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5709 0.6072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9916 1.8102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8764 0.2728 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 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6825 -1.0814 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 -2.2971 1.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2395 0.7070 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6026 0.2728 0.0000 C 0 0 1 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 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8316 -2.0702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7517 -0.7160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 2 0 0 0 0 8 16 2 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 23 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 23 1 0 0 0 0 12 24 2 0 0 0 0 13 25 2 0 0 0 0 13 28 1 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 17 22 2 0 0 0 0 17 26 1 0 0 0 0 18 19 2 0 0 0 0 19 22 1 0 0 0 0 20 18 1 6 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 21 28 1 1 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	381.16
Volume:	388.699
LogP:	2.397
LogD:	2.383
LogS:	-3.935
# Rotatable Bonds:	5
TPSA:	65.07
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.762
Synthetic Accessibility Score:	3.391
Fsp3:	0.364
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:	-4.74
MDCK Permeability:	4.4136006181361154e-05
Pgp-inhibitor:	0.94
Pgp-substrate:	0.945
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.31

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.911
Plasma Protein Binding (PPB):	85.72772216796875%
Volume Distribution (VD):	0.64
Pgp-substrate:	10.265179634094238%

ADMET: Metabolism

CYP1A2-inhibitor:	0.073
CYP1A2-substrate:	0.263
CYP2C19-inhibitor:	0.642
CYP2C19-substrate:	0.852
CYP2C9-inhibitor:	0.366
CYP2C9-substrate:	0.631
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.278
CYP3A4-inhibitor:	0.591
CYP3A4-substrate:	0.912

ADMET: Excretion

Clearance (CL):	2.245
Half-life (T1/2):	0.274

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.949
Drug-inuced Liver Injury (DILI):	0.913
AMES Toxicity:	0.144
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.442
Skin Sensitization:	0.055
Carcinogencity:	0.06
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.017

Download Data

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

Natural Product: NPC220961

Natural Product ID:	NPC220961
*Common Name:**	N,O-Diacetyl-(-)-Nornuciferidine
IUPAC Name:	[(6aS,7S)-6-acetyl-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-7-yl] acetate
Synonyms:
Standard InCHIKey:	LHFZBPLGDRPNMH-SFTDATJTSA-N
Standard InCHI:	InChI=1S/C22H23NO5/c1-12(24)23-10-9-14-11-17(26-3)22(27-4)19-15-7-5-6-8-16(15)21(28-13(2)25)20(23)18(14)19/h5-8,11,20-21H,9-10H2,1-4H3/t20-,21-/m0/s1
SMILES:	CC(=O)N1CCc2cc(c(c3-c4ccccc4[C@@H]([C@@H]1c23)OC(=O)C)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL514243
PubChem CID:	11188197
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
NPO33222	lysichiton camtschatcense	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787452]

☑ 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	1
Others	1

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		Activity	<	10.0	%	PMID[496461]
NPT1	Others	Radical scavenging activity		IC50	=	362000.0	nM	PMID[496461]

☑ 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 NPC220961 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	290
0.1-0.2	1506
0.2-0.3	6326
0.3-0.4	11596
0.4-0.5	5744
0.5-0.6	13229
0.6-0.7	3233
0.7-0.8	610
0.8-0.85	122
0.85-0.9	39
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC237579
0.8957	High Similarity	NPC476572
0.8951	High Similarity	NPC325871
0.8951	High Similarity	NPC99659
0.8869	High Similarity	NPC241055
0.8793	High Similarity	NPC156576
0.8765	High Similarity	NPC81733
0.8765	High Similarity	NPC326316
0.875	High Similarity	NPC24264
0.875	High Similarity	NPC476432
0.8736	High Similarity	NPC248642
0.8728	High Similarity	NPC267408
0.8728	High Similarity	NPC126284
0.8698	High Similarity	NPC247389
0.869	High Similarity	NPC16805
0.869	High Similarity	NPC302527
0.869	High Similarity	NPC225774
0.869	High Similarity	NPC167546
0.8639	High Similarity	NPC219341
0.8629	High Similarity	NPC116284
0.8613	High Similarity	NPC241704
0.8588	High Similarity	NPC145832
0.8588	High Similarity	NPC210918
0.8588	High Similarity	NPC117188
0.8588	High Similarity	NPC205421
0.8588	High Similarity	NPC474931
0.8588	High Similarity	NPC306555
0.8588	High Similarity	NPC158376
0.8588	High Similarity	NPC81218
0.8588	High Similarity	NPC12053
0.858	High Similarity	NPC212794
0.858	High Similarity	NPC96603
0.858	High Similarity	NPC196447
0.858	High Similarity	NPC136508
0.858	High Similarity	NPC477563
0.858	High Similarity	NPC13504
0.858	High Similarity	NPC78222
0.858	High Similarity	NPC168409
0.858	High Similarity	NPC306843
0.858	High Similarity	NPC253043
0.8521	High Similarity	NPC324144
0.8514	High Similarity	NPC32154
0.8512	High Similarity	NPC232924
0.8512	High Similarity	NPC266753
0.8512	High Similarity	NPC306902
0.8512	High Similarity	NPC160298
0.8512	High Similarity	NPC477559
0.8483	Intermediate Similarity	NPC214116
0.8443	Intermediate Similarity	NPC126519
0.8443	Intermediate Similarity	NPC203784
0.8443	Intermediate Similarity	NPC170503
0.8439	Intermediate Similarity	NPC149090
0.8439	Intermediate Similarity	NPC19520
0.8412	Intermediate Similarity	NPC1229
0.8402	Intermediate Similarity	NPC166014
0.8402	Intermediate Similarity	NPC27410
0.8389	Intermediate Similarity	NPC82763
0.8383	Intermediate Similarity	NPC244112
0.8382	Intermediate Similarity	NPC6152
0.8372	Intermediate Similarity	NPC204947
0.8372	Intermediate Similarity	NPC150879
0.8352	Intermediate Similarity	NPC114364
0.8352	Intermediate Similarity	NPC320223
0.8343	Intermediate Similarity	NPC199465
0.8343	Intermediate Similarity	NPC128560
0.8343	Intermediate Similarity	NPC229166
0.8333	Intermediate Similarity	NPC239775
0.8315	Intermediate Similarity	NPC476575
0.8286	Intermediate Similarity	NPC477020
0.8286	Intermediate Similarity	NPC192135
0.8286	Intermediate Similarity	NPC66341
0.8276	Intermediate Similarity	NPC118274
0.8276	Intermediate Similarity	NPC168753
0.8276	Intermediate Similarity	NPC69712
0.8276	Intermediate Similarity	NPC26240
0.8276	Intermediate Similarity	NPC477562
0.8266	Intermediate Similarity	NPC298979
0.8256	Intermediate Similarity	NPC169743
0.8249	Intermediate Similarity	NPC118633
0.8249	Intermediate Similarity	NPC148693
0.8249	Intermediate Similarity	NPC294790
0.8225	Intermediate Similarity	NPC323443
0.8225	Intermediate Similarity	NPC180756
0.8208	Intermediate Similarity	NPC304659
0.8208	Intermediate Similarity	NPC86144
0.8198	Intermediate Similarity	NPC233650
0.8197	Intermediate Similarity	NPC117717
0.8182	Intermediate Similarity	NPC210437
0.8182	Intermediate Similarity	NPC106295
0.8182	Intermediate Similarity	NPC51957
0.8182	Intermediate Similarity	NPC16107
0.8182	Intermediate Similarity	NPC476144
0.8167	Intermediate Similarity	NPC302275
0.8161	Intermediate Similarity	NPC474324
0.8161	Intermediate Similarity	NPC57812
0.8156	Intermediate Similarity	NPC32413
0.8156	Intermediate Similarity	NPC474506
0.815	Intermediate Similarity	NPC134858
0.8148	Intermediate Similarity	NPC188163
0.8148	Intermediate Similarity	NPC213206
0.8148	Intermediate Similarity	NPC470925
0.8148	Intermediate Similarity	NPC328750
0.8148	Intermediate Similarity	NPC474915
0.8146	Intermediate Similarity	NPC23219
0.8142	Intermediate Similarity	NPC475754
0.814	Intermediate Similarity	NPC60186
0.8133	Intermediate Similarity	NPC7467
0.8114	Intermediate Similarity	NPC475845
0.8111	Intermediate Similarity	NPC233718
0.8103	Intermediate Similarity	NPC35627
0.8103	Intermediate Similarity	NPC81247
0.8103	Intermediate Similarity	NPC476573
0.8101	Intermediate Similarity	NPC470879
0.8101	Intermediate Similarity	NPC258695
0.8101	Intermediate Similarity	NPC474507
0.8092	Intermediate Similarity	NPC189470
0.809	Intermediate Similarity	NPC112575
0.8086	Intermediate Similarity	NPC314682
0.8084	Intermediate Similarity	NPC92541
0.8084	Intermediate Similarity	NPC219162
0.8079	Intermediate Similarity	NPC2314
0.8068	Intermediate Similarity	NPC474708
0.8066	Intermediate Similarity	NPC135772
0.8057	Intermediate Similarity	NPC210140
0.8056	Intermediate Similarity	NPC155442
0.8056	Intermediate Similarity	NPC312918
0.8056	Intermediate Similarity	NPC477561
0.8056	Intermediate Similarity	NPC476574
0.8049	Intermediate Similarity	NPC128019
0.8049	Intermediate Similarity	NPC136860
0.8049	Intermediate Similarity	NPC476567
0.8047	Intermediate Similarity	NPC470924
0.8045	Intermediate Similarity	NPC190461
0.8034	Intermediate Similarity	NPC477558
0.8024	Intermediate Similarity	NPC130941
0.7989	Intermediate Similarity	NPC148709
0.7989	Intermediate Similarity	NPC474470
0.7989	Intermediate Similarity	NPC476577
0.7989	Intermediate Similarity	NPC173416
0.7978	Intermediate Similarity	NPC14507
0.7978	Intermediate Similarity	NPC47077
0.7964	Intermediate Similarity	NPC144863
0.7964	Intermediate Similarity	NPC90844
0.7964	Intermediate Similarity	NPC253883
0.7964	Intermediate Similarity	NPC95075
0.7953	Intermediate Similarity	NPC216459
0.7953	Intermediate Similarity	NPC123323
0.7953	Intermediate Similarity	NPC41178
0.7953	Intermediate Similarity	NPC138487
0.7946	Intermediate Similarity	NPC475597
0.7946	Intermediate Similarity	NPC473716
0.7933	Intermediate Similarity	NPC304675
0.7919	Intermediate Similarity	NPC477080
0.7917	Intermediate Similarity	NPC475959
0.7912	Intermediate Similarity	NPC275132
0.7907	Intermediate Similarity	NPC146288
0.7903	Intermediate Similarity	NPC478093
0.7903	Intermediate Similarity	NPC78284
0.7898	Intermediate Similarity	NPC124657
0.7889	Intermediate Similarity	NPC237044
0.788	Intermediate Similarity	NPC57036
0.7877	Intermediate Similarity	NPC285941
0.7865	Intermediate Similarity	NPC152212
0.7861	Intermediate Similarity	NPC478092
0.7861	Intermediate Similarity	NPC478091
0.7861	Intermediate Similarity	NPC30182
0.7861	Intermediate Similarity	NPC473589
0.7857	Intermediate Similarity	NPC115906
0.7857	Intermediate Similarity	NPC476151
0.7849	Intermediate Similarity	NPC204828
0.7849	Intermediate Similarity	NPC295691
0.7849	Intermediate Similarity	NPC469817
0.7849	Intermediate Similarity	NPC278799
0.7849	Intermediate Similarity	NPC172765
0.7849	Intermediate Similarity	NPC189266
0.7849	Intermediate Similarity	NPC110416
0.7849	Intermediate Similarity	NPC2413
0.7849	Intermediate Similarity	NPC207757
0.7849	Intermediate Similarity	NPC184026
0.7849	Intermediate Similarity	NPC39701
0.7849	Intermediate Similarity	NPC54379
0.7849	Intermediate Similarity	NPC193949
0.7849	Intermediate Similarity	NPC249797
0.7849	Intermediate Similarity	NPC5238
0.7849	Intermediate Similarity	NPC276588
0.7849	Intermediate Similarity	NPC127674
0.7845	Intermediate Similarity	NPC474325
0.7845	Intermediate Similarity	NPC477560
0.7844	Intermediate Similarity	NPC185838
0.7841	Intermediate Similarity	NPC247972
0.7841	Intermediate Similarity	NPC231198
0.7838	Intermediate Similarity	NPC186546
0.7838	Intermediate Similarity	NPC312531
0.7838	Intermediate Similarity	NPC476576
0.7831	Intermediate Similarity	NPC124302
0.7831	Intermediate Similarity	NPC14622
0.7831	Intermediate Similarity	NPC46744
0.7831	Intermediate Similarity	NPC215098
0.7831	Intermediate Similarity	NPC70290
0.7831	Intermediate Similarity	NPC73020

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 NPC220961 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	680
0.2-0.3	1095
0.3-0.4	2008
0.4-0.5	2514
0.5-0.6	1886
0.6-0.7	607
0.7-0.8	161
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8538	High Similarity	NPD4481	Phase 3
0.8306	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD4584	Approved
0.8148	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD3051	Approved
0.8011	Intermediate Similarity	NPD6851	Approved
0.8011	Intermediate Similarity	NPD6853	Approved
0.7978	Intermediate Similarity	NPD7906	Approved
0.7955	Intermediate Similarity	NPD2970	Approved
0.7955	Intermediate Similarity	NPD2969	Approved
0.7943	Intermediate Similarity	NPD6107	Approved
0.7889	Intermediate Similarity	NPD6297	Approved
0.7877	Intermediate Similarity	NPD8156	Discontinued
0.7877	Intermediate Similarity	NPD5312	Approved
0.7877	Intermediate Similarity	NPD5313	Approved
0.7857	Intermediate Similarity	NPD4578	Approved
0.7857	Intermediate Similarity	NPD2968	Approved
0.7857	Intermediate Similarity	NPD4577	Approved
0.7857	Intermediate Similarity	NPD2971	Approved
0.7831	Intermediate Similarity	NPD4420	Approved
0.7829	Intermediate Similarity	NPD7400	Phase 3
0.7826	Intermediate Similarity	NPD4663	Approved
0.7821	Intermediate Similarity	NPD8251	Approved
0.7821	Intermediate Similarity	NPD8252	Approved
0.7821	Intermediate Similarity	NPD8099	Discontinued
0.7809	Intermediate Similarity	NPD2489	Approved
0.7809	Intermediate Similarity	NPD27	Approved
0.7803	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD5241	Discontinued
0.7778	Intermediate Similarity	NPD2973	Approved
0.7778	Intermediate Similarity	NPD2975	Approved
0.7778	Intermediate Similarity	NPD2974	Approved
0.7739	Intermediate Similarity	NPD7047	Phase 3
0.7692	Intermediate Similarity	NPD2421	Approved
0.7692	Intermediate Similarity	NPD2420	Approved
0.7685	Intermediate Similarity	NPD6997	Phase 2
0.7684	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD42	Phase 2
0.768	Intermediate Similarity	NPD6042	Phase 2
0.7668	Intermediate Similarity	NPD5005	Approved
0.7668	Intermediate Similarity	NPD5006	Approved
0.7656	Intermediate Similarity	NPD4580	Approved
0.7633	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD3452	Approved
0.7617	Intermediate Similarity	NPD2494	Approved
0.7617	Intermediate Similarity	NPD2493	Approved
0.7617	Intermediate Similarity	NPD3450	Approved
0.7616	Intermediate Similarity	NPD4210	Discontinued
0.7614	Intermediate Similarity	NPD6788	Approved
0.7584	Intermediate Similarity	NPD5677	Discontinued
0.7574	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD4017	Approved
0.7568	Intermediate Similarity	NPD7311	Approved
0.7568	Intermediate Similarity	NPD7313	Approved
0.7568	Intermediate Similarity	NPD7312	Approved
0.7568	Intermediate Similarity	NPD7310	Approved
0.7558	Intermediate Similarity	NPD6030	Approved
0.7558	Intermediate Similarity	NPD3640	Phase 3
0.7558	Intermediate Similarity	NPD3639	Approved
0.7558	Intermediate Similarity	NPD3641	Approved
0.7558	Intermediate Similarity	NPD6031	Approved
0.7543	Intermediate Similarity	NPD7298	Approved
0.753	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD8054	Approved
0.7527	Intermediate Similarity	NPD8053	Approved
0.7527	Intermediate Similarity	NPD7309	Approved
0.7513	Intermediate Similarity	NPD2490	Approved
0.7513	Intermediate Similarity	NPD2488	Approved
0.75	Intermediate Similarity	NPD4582	Approved
0.75	Intermediate Similarity	NPD4583	Approved
0.75	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4773	Phase 2
0.7486	Intermediate Similarity	NPD4772	Phase 2
0.7474	Intermediate Similarity	NPD4107	Approved
0.7449	Intermediate Similarity	NPD4002	Approved
0.7449	Intermediate Similarity	NPD4004	Approved
0.743	Intermediate Similarity	NPD5709	Phase 3
0.7418	Intermediate Similarity	NPD2898	Approved
0.7416	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD5754	Discontinued
0.7407	Intermediate Similarity	NPD7291	Discontinued
0.7403	Intermediate Similarity	NPD6071	Discontinued
0.7403	Intermediate Similarity	NPD4166	Phase 2
0.7394	Intermediate Similarity	NPD3109	Approved
0.7394	Intermediate Similarity	NPD3110	Approved
0.7389	Intermediate Similarity	NPD4666	Phase 3
0.7374	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7831	Phase 2
0.7374	Intermediate Similarity	NPD7833	Phase 2
0.736	Intermediate Similarity	NPD2563	Approved
0.736	Intermediate Similarity	NPD2560	Approved
0.7356	Intermediate Similarity	NPD5976	Discontinued
0.7356	Intermediate Similarity	NPD4727	Phase 1
0.7353	Intermediate Similarity	NPD4236	Phase 3
0.7353	Intermediate Similarity	NPD4237	Approved
0.7347	Intermediate Similarity	NPD4482	Phase 3
0.7341	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1753	Discontinued
0.7305	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7110	Phase 1
0.7288	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD5242	Approved
0.7268	Intermediate Similarity	NPD6687	Approved
0.7268	Intermediate Similarity	NPD6688	Approved
0.7267	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD1914	Approved
0.7243	Intermediate Similarity	NPD7177	Discontinued
0.7234	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4475	Approved
0.7229	Intermediate Similarity	NPD4474	Approved
0.7225	Intermediate Similarity	NPD6666	Approved
0.7225	Intermediate Similarity	NPD6667	Approved
0.7198	Intermediate Similarity	NPD2904	Discontinued
0.7196	Intermediate Similarity	NPD7280	Phase 3
0.7196	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7281	Phase 3
0.7191	Intermediate Similarity	NPD6386	Approved
0.7191	Intermediate Similarity	NPD6385	Approved
0.7179	Intermediate Similarity	NPD5582	Discontinued
0.7175	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD5718	Phase 2
0.7166	Intermediate Similarity	NPD3885	Approved
0.7159	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7802	Discontinued
0.7152	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3146	Approved
0.7143	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6496	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4010	Discontinued
0.7108	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6090	Discontinued
0.7098	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7048	Phase 3
0.7095	Intermediate Similarity	NPD1757	Discontinued
0.7088	Intermediate Similarity	NPD4055	Discovery
0.7071	Intermediate Similarity	NPD8095	Phase 1
0.7069	Intermediate Similarity	NPD5160	Discontinued
0.7068	Intermediate Similarity	NPD6618	Phase 2
0.7062	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7427	Discontinued
0.7056	Intermediate Similarity	NPD5564	Approved
0.7053	Intermediate Similarity	NPD7549	Discontinued
0.7052	Intermediate Similarity	NPD3060	Approved
0.705	Intermediate Similarity	NPD3057	Approved
0.7045	Intermediate Similarity	NPD1424	Approved
0.7045	Intermediate Similarity	NPD4123	Phase 3
0.7039	Intermediate Similarity	NPD6875	Approved
0.7039	Intermediate Similarity	NPD6876	Approved
0.7039	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5457	Discontinued
0.7029	Intermediate Similarity	NPD3845	Phase 1
0.7029	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6747	Phase 1
0.7024	Intermediate Similarity	NPD5676	Approved
0.7022	Intermediate Similarity	NPD3686	Approved
0.7022	Intermediate Similarity	NPD3687	Approved
0.7021	Intermediate Similarity	NPD5096	Phase 3
0.7021	Intermediate Similarity	NPD5095	Phase 3
0.7011	Intermediate Similarity	NPD6037	Discontinued
0.7011	Intermediate Similarity	NPD6748	Discontinued
0.7011	Intermediate Similarity	NPD2041	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2042	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5938	Phase 3
0.7005	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7039	Approved
0.7	Intermediate Similarity	NPD7038	Approved
0.6994	Remote Similarity	NPD2897	Discontinued
0.699	Remote Similarity	NPD7827	Phase 1
0.6989	Remote Similarity	NPD2388	Discontinued
0.6989	Remote Similarity	NPD3124	Discontinued
0.6984	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4040	Phase 1
0.6978	Remote Similarity	NPD5977	Approved
0.6978	Remote Similarity	NPD5978	Approved
0.6965	Remote Similarity	NPD2972	Approved
0.6965	Remote Similarity	NPD3533	Approved
0.6964	Remote Similarity	NPD7294	Phase 1
0.6964	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6896	Approved
0.6959	Remote Similarity	NPD6895	Approved
0.6959	Remote Similarity	NPD2200	Suspended
0.6954	Remote Similarity	NPD5177	Phase 3
0.6954	Remote Similarity	NPD4162	Approved
0.6938	Remote Similarity	NPD5980	Discovery
0.6936	Remote Similarity	NPD4725	Approved
0.6936	Remote Similarity	NPD4721	Approved
0.6936	Remote Similarity	NPD4726	Approved
0.6936	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7124	Phase 2
0.6931	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD3933	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