NPASS Compound

Structure

NPC476249 OpenBabel07101718222D 25 28 0 0 0 0 0 0 0 0999 V2000 9.0594 -5.2556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8383 -0.4890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2294 -4.1306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0997 -2.6233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3592 -3.6281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2294 -2.1209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9699 -4.1306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6623 -2.6663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8401 -3.6281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7673 -3.6656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2556 -4.0884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4338 -1.3019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0997 -3.6281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7443 -2.2576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3592 -2.6233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5805 -3.6281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0364 -3.8476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9314 -2.8482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1184 -2.2576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5195 -2.8133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7103 -4.1306 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.9544 -4.2563 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.4289 -1.3019 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 0.4890 -2.1209 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 5.5841 -2.4462 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 5 1 0 0 0 0 3 13 2 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 15 2 0 0 0 0 6 15 1 0 0 0 0 7 9 2 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 16 1 0 0 0 0 11 17 2 0 0 0 0 12 14 1 0 0 0 0 12 23 2 0 0 0 0 14 18 2 0 0 0 0 15 24 1 0 0 0 0 16 20 1 0 0 0 0 16 21 2 0 0 0 0 17 18 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 19 20 2 0 0 0 0 19 23 1 0 0 0 0 20 25 1 0 0 0 0 M CHG 2 23 1 24 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	333.15
Volume:	347.093
LogP:	2.964
LogD:	2.187
LogS:	-1.786
# Rotatable Bonds:	3
TPSA:	61.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.663
Synthetic Accessibility Score:	4.347
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.896
MDCK Permeability:	2.4373188352910802e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.95
Human Intestinal Absorption (HIA):	0.377
20% Bioavailability (F20%):	0.708
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.749
Plasma Protein Binding (PPB):	92.73636627197266%
Volume Distribution (VD):	1.319
Pgp-substrate:	9.618753433227539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.747
CYP1A2-substrate:	0.224
CYP2C19-inhibitor:	0.168
CYP2C19-substrate:	0.301
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.467
CYP2D6-inhibitor:	0.758
CYP2D6-substrate:	0.813
CYP3A4-inhibitor:	0.038
CYP3A4-substrate:	0.33

ADMET: Excretion

Clearance (CL):	2.114
Half-life (T1/2):	0.846

ADMET: Toxicity

hERG Blockers:	0.1
Human Hepatotoxicity (H-HT):	0.73
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.65
Rat Oral Acute Toxicity:	0.441
Maximum Recommended Daily Dose:	0.894
Skin Sensitization:	0.917
Carcinogencity:	0.922
Eye Corrosion:	0.003
Eye Irritation:	0.059
Respiratory Toxicity:	0.901

Download Data

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

Natural Product: NPC476249

Natural Product ID:	NPC476249
*Common Name:**	Makaluvamine G
IUPAC Name:	n.a.
Synonyms:	Makaluvamine G; Makaluvamines G Trifluroacetate
Standard InCHIKey:	OZFIOCHCUGXKME-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H19N3O2.C2HF3O2/c1-22-10-8-14-12-23(2)19-18(14)17(22)11-16(20(19)25)21-9-7-13-3-5-15(24)6-4-13;3-2(4,5)1(6)7/h3-7,9,11-12H,8,10H2,1-2H3,(H,24,25);(H,6,7)
SMILES:	OC(=O)C(F)(F)F.[O-]c1ccc(cc1)C=CN=C1C=C2N(C)CCC3=C2C(=C1O)[N+](=C3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL558428
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001734] Pyrroloquinolines [CHEMONTID:0002829] Pyrrolo[4,3,2-de]quinolines

*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
NPO32549	zyzzya fuliginosa	Species	n.a.	Eukaryota	n.a.	indopacific	n.a.	PMID[12027767]
NPO32549	zyzzya fuliginosa	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[16180829]
NPO33461	zyzzya sp.	Species	n.a.	Eukaryota	n.a.	Australian	n.a.	PMID[22686608]
NPO32549	zyzzya fuliginosa	Species	n.a.	Eukaryota	n.a.	pohnpeian	n.a.	PMID[8691207]
NPO32549	zyzzya fuliginosa	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[9134749]

☑ 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	3
Others	12

Activity Type	# Activity
Cell Line	1
Organism	8
Others	2
Subcellular	2
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	2000.0	nM	PMID[523020]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	36.0	nM	PMID[523020]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	39.0	nM	PMID[523020]
NPT2	Others	Unspecified		Ratio IC50	=	55.0	n.a.	PMID[523020]
NPT2	Others	Unspecified		Ratio IC50	=	51.0	n.a.	PMID[523020]
NPT433	Subcellular	Liver microsomes	Homo sapiens	T1/2	=	0.1467	hr	PMID[523020]
NPT625	Tissue	Liver	Mus musculus	T1/2	=	0.1233	hr	PMID[523020]
NPT433	Subcellular	Liver microsomes	Homo sapiens	CLH	=	197.0	uL/min	PMID[523020]
NPT625	Tissue	Liver	Mus musculus	CLH	=	235.0	uL/min	PMID[523020]
NPT32	Organism	Mus musculus	Mus musculus	Cp	<	0.04	uM	PMID[523020]
NPT32	Organism	Mus musculus	Mus musculus	MTD	=	8.0	mg/kg/day	PMID[523020]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	10.0	%	PMID[523020]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	35.0	%	PMID[523020]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	47.0	%	PMID[523020]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	48.0	%	PMID[523020]

☑ 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 NPC476249 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	175
0.1-0.2	1736
0.2-0.3	9411
0.3-0.4	8919
0.4-0.5	17377
0.5-0.6	4689
0.6-0.7	381
0.7-0.8	7
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8129	Intermediate Similarity	NPC473804
0.8071	Intermediate Similarity	NPC119569
0.7656	Intermediate Similarity	NPC82963
0.7638	Intermediate Similarity	NPC118202
0.7597	Intermediate Similarity	NPC311737
0.7597	Intermediate Similarity	NPC38458
0.7561	Intermediate Similarity	NPC231705
0.75	Intermediate Similarity	NPC142297
0.7442	Intermediate Similarity	NPC37302
0.744	Intermediate Similarity	NPC96224
0.744	Intermediate Similarity	NPC24101
0.7385	Intermediate Similarity	NPC258992
0.7381	Intermediate Similarity	NPC258056
0.7368	Intermediate Similarity	NPC473051
0.7368	Intermediate Similarity	NPC473050
0.7323	Intermediate Similarity	NPC474149
0.7317	Intermediate Similarity	NPC178902
0.7308	Intermediate Similarity	NPC317254
0.7308	Intermediate Similarity	NPC303370
0.7197	Intermediate Similarity	NPC323948
0.7165	Intermediate Similarity	NPC153690
0.7164	Intermediate Similarity	NPC41801
0.7163	Intermediate Similarity	NPC274732
0.7154	Intermediate Similarity	NPC289381
0.7154	Intermediate Similarity	NPC155847
0.7113	Intermediate Similarity	NPC184437
0.7111	Intermediate Similarity	NPC83279
0.709	Intermediate Similarity	NPC256369
0.709	Intermediate Similarity	NPC283760
0.7042	Intermediate Similarity	NPC471953
0.7037	Intermediate Similarity	NPC252817
0.7031	Intermediate Similarity	NPC146530
0.7	Intermediate Similarity	NPC166837
0.6977	Remote Similarity	NPC470127
0.6966	Remote Similarity	NPC242159
0.6966	Remote Similarity	NPC313694
0.6963	Remote Similarity	NPC43275
0.695	Remote Similarity	NPC271808
0.6944	Remote Similarity	NPC29650
0.694	Remote Similarity	NPC283468
0.6939	Remote Similarity	NPC189724
0.6939	Remote Similarity	NPC212850
0.6939	Remote Similarity	NPC83289
0.6933	Remote Similarity	NPC9373
0.6911	Remote Similarity	NPC33168
0.6897	Remote Similarity	NPC138365
0.6889	Remote Similarity	NPC122009
0.6871	Remote Similarity	NPC476989
0.6867	Remote Similarity	NPC247298
0.6855	Remote Similarity	NPC107619
0.6838	Remote Similarity	NPC268572
0.6835	Remote Similarity	NPC307020
0.6812	Remote Similarity	NPC474862
0.6788	Remote Similarity	NPC263835
0.6783	Remote Similarity	NPC474091
0.6783	Remote Similarity	NPC120251
0.6781	Remote Similarity	NPC237227
0.6776	Remote Similarity	NPC245974
0.6769	Remote Similarity	NPC309982
0.6739	Remote Similarity	NPC324702
0.6718	Remote Similarity	NPC316052
0.6716	Remote Similarity	NPC142599
0.669	Remote Similarity	NPC328070
0.669	Remote Similarity	NPC244866
0.6689	Remote Similarity	NPC193528
0.6667	Remote Similarity	NPC321133
0.6667	Remote Similarity	NPC62101
0.6667	Remote Similarity	NPC95733
0.6667	Remote Similarity	NPC160120
0.6667	Remote Similarity	NPC471308
0.6667	Remote Similarity	NPC53596
0.6667	Remote Similarity	NPC171372
0.6667	Remote Similarity	NPC17388
0.6667	Remote Similarity	NPC289330
0.6645	Remote Similarity	NPC16188
0.6644	Remote Similarity	NPC150712
0.6644	Remote Similarity	NPC267237
0.6643	Remote Similarity	NPC66177
0.6643	Remote Similarity	NPC471315
0.6643	Remote Similarity	NPC268763
0.6643	Remote Similarity	NPC8305
0.6643	Remote Similarity	NPC186898
0.6643	Remote Similarity	NPC471314
0.6642	Remote Similarity	NPC5932
0.6625	Remote Similarity	NPC191863
0.6625	Remote Similarity	NPC289776
0.6625	Remote Similarity	NPC133470
0.6621	Remote Similarity	NPC326966
0.6621	Remote Similarity	NPC475735
0.6621	Remote Similarity	NPC257390
0.662	Remote Similarity	NPC29477
0.6619	Remote Similarity	NPC86966
0.66	Remote Similarity	NPC168861
0.6599	Remote Similarity	NPC473360
0.6597	Remote Similarity	NPC478147
0.6597	Remote Similarity	NPC325651
0.6596	Remote Similarity	NPC211218
0.6594	Remote Similarity	NPC319950
0.6585	Remote Similarity	NPC270547
0.6581	Remote Similarity	NPC233702
0.6577	Remote Similarity	NPC471201
0.6575	Remote Similarity	NPC118419
0.6573	Remote Similarity	NPC218323
0.6571	Remote Similarity	NPC93390
0.656	Remote Similarity	NPC26244
0.6557	Remote Similarity	NPC98772
0.6557	Remote Similarity	NPC177420
0.6557	Remote Similarity	NPC280347
0.6557	Remote Similarity	NPC172128
0.6552	Remote Similarity	NPC99280
0.6547	Remote Similarity	NPC112823
0.6543	Remote Similarity	NPC471178
0.6536	Remote Similarity	NPC83790
0.6536	Remote Similarity	NPC128237
0.6535	Remote Similarity	NPC125732
0.6529	Remote Similarity	NPC184169
0.6528	Remote Similarity	NPC251571
0.6528	Remote Similarity	NPC296712
0.6525	Remote Similarity	NPC477163
0.6522	Remote Similarity	NPC124542
0.6522	Remote Similarity	NPC59779
0.6522	Remote Similarity	NPC471177
0.6519	Remote Similarity	NPC309808
0.6516	Remote Similarity	NPC473491
0.6513	Remote Similarity	NPC266741
0.651	Remote Similarity	NPC473052
0.651	Remote Similarity	NPC473055
0.6508	Remote Similarity	NPC473388
0.6508	Remote Similarity	NPC311242
0.6507	Remote Similarity	NPC45191
0.6507	Remote Similarity	NPC476570
0.6504	Remote Similarity	NPC55561
0.65	Remote Similarity	NPC284078
0.65	Remote Similarity	NPC248817
0.6497	Remote Similarity	NPC78767
0.6497	Remote Similarity	NPC473814
0.6493	Remote Similarity	NPC163674
0.6493	Remote Similarity	NPC227553
0.6486	Remote Similarity	NPC303993
0.6486	Remote Similarity	NPC120114
0.6486	Remote Similarity	NPC470441
0.6486	Remote Similarity	NPC71888
0.6484	Remote Similarity	NPC29601
0.6483	Remote Similarity	NPC124802
0.6483	Remote Similarity	NPC155838
0.6483	Remote Similarity	NPC226662
0.648	Remote Similarity	NPC303045
0.648	Remote Similarity	NPC151715
0.648	Remote Similarity	NPC161972
0.6475	Remote Similarity	NPC113460
0.6475	Remote Similarity	NPC25493
0.6471	Remote Similarity	NPC81026
0.6467	Remote Similarity	NPC214988
0.6467	Remote Similarity	NPC322526
0.6467	Remote Similarity	NPC197045
0.6466	Remote Similarity	NPC292758
0.6466	Remote Similarity	NPC65855
0.6463	Remote Similarity	NPC247018
0.6463	Remote Similarity	NPC307123
0.6463	Remote Similarity	NPC97870
0.6458	Remote Similarity	NPC301713
0.6458	Remote Similarity	NPC251466
0.6458	Remote Similarity	NPC305717
0.6456	Remote Similarity	NPC244509
0.6456	Remote Similarity	NPC476268
0.6454	Remote Similarity	NPC27581
0.645	Remote Similarity	NPC39822
0.6447	Remote Similarity	NPC474128
0.6446	Remote Similarity	NPC248670
0.6446	Remote Similarity	NPC198747
0.6446	Remote Similarity	NPC197783
0.6443	Remote Similarity	NPC470471
0.6443	Remote Similarity	NPC11147
0.6443	Remote Similarity	NPC64205
0.6443	Remote Similarity	NPC6570
0.6438	Remote Similarity	NPC259665
0.6438	Remote Similarity	NPC35961
0.6438	Remote Similarity	NPC470706
0.6438	Remote Similarity	NPC89769
0.6438	Remote Similarity	NPC244336
0.6438	Remote Similarity	NPC195749
0.6438	Remote Similarity	NPC52029
0.6438	Remote Similarity	NPC126859
0.6434	Remote Similarity	NPC474479
0.6433	Remote Similarity	NPC202198
0.6433	Remote Similarity	NPC258222
0.6423	Remote Similarity	NPC213
0.6423	Remote Similarity	NPC318325
0.6423	Remote Similarity	NPC123273
0.6423	Remote Similarity	NPC10286
0.6423	Remote Similarity	NPC242240
0.6423	Remote Similarity	NPC476160
0.642	Remote Similarity	NPC476231
0.6419	Remote Similarity	NPC163810
0.6419	Remote Similarity	NPC169766
0.6417	Remote Similarity	NPC265146
0.6417	Remote Similarity	NPC124436
0.6414	Remote Similarity	NPC202776
0.6414	Remote Similarity	NPC191302
0.6414	Remote Similarity	NPC153990

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 NPC476249 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	119
0.1-0.2	482
0.2-0.3	1011
0.3-0.4	1308
0.4-0.5	3964
0.5-0.6	2169
0.6-0.7	97
0.7-0.8	0
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
0.7372	Intermediate Similarity	NPD4993	Discontinued
0.7368	Intermediate Similarity	NPD3421	Phase 3
0.7143	Intermediate Similarity	NPD5481	Discontinued
0.7023	Intermediate Similarity	NPD2234	Approved
0.7023	Intermediate Similarity	NPD2229	Approved
0.7023	Intermediate Similarity	NPD2228	Approved
0.6954	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7451	Discontinued
0.6912	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2789	Approved
0.6889	Remote Similarity	NPD5304	Approved
0.6889	Remote Similarity	NPD5303	Approved
0.6879	Remote Similarity	NPD5599	Discontinued
0.6838	Remote Similarity	NPD4093	Discontinued
0.6835	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4659	Approved
0.68	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6346	Approved
0.6744	Remote Similarity	NPD1445	Approved
0.6744	Remote Similarity	NPD1444	Approved
0.6738	Remote Similarity	NPD4103	Phase 2
0.6738	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD1792	Phase 2
0.671	Remote Similarity	NPD5267	Discontinued
0.6692	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2667	Approved
0.6667	Remote Similarity	NPD2668	Approved
0.6667	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2562	Approved
0.6643	Remote Similarity	NPD2561	Approved
0.6643	Remote Similarity	NPD3636	Approved
0.6643	Remote Similarity	NPD3637	Approved
0.6643	Remote Similarity	NPD3635	Approved
0.6642	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD3553	Approved
0.6622	Remote Similarity	NPD3552	Approved
0.6622	Remote Similarity	NPD3554	Approved
0.6622	Remote Similarity	NPD3555	Approved
0.6619	Remote Similarity	NPD3143	Discontinued
0.6613	Remote Similarity	NPD2933	Approved
0.6613	Remote Similarity	NPD2934	Approved
0.6606	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD2210	Approved
0.6594	Remote Similarity	NPD2212	Approved
0.6589	Remote Similarity	NPD9608	Approved
0.6589	Remote Similarity	NPD9610	Approved
0.6579	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD16	Approved
0.6569	Remote Similarity	NPD856	Approved
0.656	Remote Similarity	NPD2860	Approved
0.656	Remote Similarity	NPD2859	Approved
0.6552	Remote Similarity	NPD2372	Approved
0.6552	Remote Similarity	NPD3136	Phase 2
0.6547	Remote Similarity	NPD1751	Approved
0.6545	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD1725	Approved
0.6513	Remote Similarity	NPD44	Approved
0.6513	Remote Similarity	NPD6364	Approved
0.6513	Remote Similarity	NPD2458	Approved
0.6513	Remote Similarity	NPD2460	Phase 3
0.6513	Remote Similarity	NPD2459	Approved
0.6506	Remote Similarity	NPD4443	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD3053	Approved
0.6503	Remote Similarity	NPD3055	Approved
0.6483	Remote Similarity	NPD2606	Approved
0.6483	Remote Similarity	NPD2605	Approved
0.6483	Remote Similarity	NPD3594	Approved
0.6483	Remote Similarity	NPD3595	Approved
0.6478	Remote Similarity	NPD2468	Approved
0.6478	Remote Similarity	NPD2469	Approved
0.6471	Remote Similarity	NPD1791	Approved
0.6471	Remote Similarity	NPD1793	Approved
0.6463	Remote Similarity	NPD7477	Discontinued
0.6463	Remote Similarity	NPD1423	Approved
0.6463	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD3151	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD317	Approved
0.6449	Remote Similarity	NPD1758	Phase 1
0.6449	Remote Similarity	NPD318	Approved
0.6447	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD821	Approved
0.6438	Remote Similarity	NPD5155	Approved
0.6438	Remote Similarity	NPD5156	Approved
0.6434	Remote Similarity	NPD4817	Approved
0.6434	Remote Similarity	NPD5310	Approved
0.6434	Remote Similarity	NPD5311	Approved
0.6434	Remote Similarity	NPD4818	Approved
0.6429	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD7450	Phase 2
0.6418	Remote Similarity	NPD2583	Phase 2
0.6417	Remote Similarity	NPD111	Approved
0.6415	Remote Similarity	NPD2592	Discontinued
0.6408	Remote Similarity	NPD3070	Discontinued
0.6406	Remote Similarity	NPD3020	Approved
0.6403	Remote Similarity	NPD1759	Phase 1
0.6398	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD3144	Approved
0.6395	Remote Similarity	NPD3145	Approved
0.6392	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD3681	Approved
0.6385	Remote Similarity	NPD4658	Approved
0.6385	Remote Similarity	NPD3683	Approved
0.6385	Remote Similarity	NPD3680	Approved
0.6385	Remote Similarity	NPD3682	Approved
0.6385	Remote Similarity	NPD4231	Approved
0.6385	Remote Similarity	NPD4656	Approved
0.6385	Remote Similarity	NPD4229	Approved
0.6382	Remote Similarity	NPD3656	Approved
0.6377	Remote Similarity	NPD3123	Discovery
0.6369	Remote Similarity	NPD7303	Discontinued
0.6364	Remote Similarity	NPD2889	Approved
0.6364	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1669	Approved
0.6364	Remote Similarity	NPD2888	Approved
0.6364	Remote Similarity	NPD6582	Phase 2
0.6364	Remote Similarity	NPD2017	Approved
0.6364	Remote Similarity	NPD6331	Phase 2
0.6364	Remote Similarity	NPD6583	Phase 3
0.6364	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2890	Approved
0.6358	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD6380	Phase 1
0.6357	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD2674	Phase 3
0.6351	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.634	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD7131	Phase 3
0.6329	Remote Similarity	NPD2122	Discontinued
0.6328	Remote Similarity	NPD9273	Approved
0.6323	Remote Similarity	NPD3692	Discontinued
0.6319	Remote Similarity	NPD2922	Phase 1
0.6319	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2161	Phase 2
0.6316	Remote Similarity	NPD9507	Approved
0.6308	Remote Similarity	NPD4119	Approved
0.6308	Remote Similarity	NPD854	Approved
0.6308	Remote Similarity	NPD855	Approved
0.6306	Remote Similarity	NPD2874	Phase 2
0.6306	Remote Similarity	NPD2335	Discontinued
0.6299	Remote Similarity	NPD2211	Approved
0.6299	Remote Similarity	NPD2209	Approved
0.6296	Remote Similarity	NPD4253	Approved
0.6296	Remote Similarity	NPD4254	Approved
0.6294	Remote Similarity	NPD2233	Approved
0.6294	Remote Similarity	NPD2232	Approved
0.6294	Remote Similarity	NPD2230	Approved
0.6288	Remote Similarity	NPD5717	Approved
0.6284	Remote Similarity	NPD1039	Discontinued
0.6282	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD3149	Approved
0.6277	Remote Similarity	NPD3150	Approved
0.6277	Remote Similarity	NPD2658	Approved
0.6277	Remote Similarity	NPD3147	Approved
0.6277	Remote Similarity	NPD3148	Approved
0.6277	Remote Similarity	NPD2659	Approved
0.6276	Remote Similarity	NPD1133	Approved
0.6276	Remote Similarity	NPD1131	Approved
0.6276	Remote Similarity	NPD1134	Approved
0.6276	Remote Similarity	NPD1129	Approved
0.6276	Remote Similarity	NPD1135	Approved
0.6273	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD1671	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD2791	Discontinued
0.6266	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD2781	Approved
0.6265	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD3596	Phase 2
0.6258	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5811	Approved
0.625	Remote Similarity	NPD1755	Approved
0.625	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD2782	Approved
0.6242	Remote Similarity	NPD2780	Approved
0.6242	Remote Similarity	NPD5745	Approved
0.6241	Remote Similarity	NPD6382	Discontinued
0.6241	Remote Similarity	NPD2595	Approved
0.6241	Remote Similarity	NPD2594	Approved
0.6233	Remote Similarity	NPD6584	Phase 3
0.6233	Remote Similarity	NPD7018	Phase 2
0.6232	Remote Similarity	NPD475	Phase 2
0.6232	Remote Similarity	NPD5631	Phase 3
0.6229	Remote Similarity	NPD4951	Discontinued
0.6225	Remote Similarity	NPD2157	Approved
0.6224	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD3386	Phase 2

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