NPASS Compound

Structure

NPC43219 OpenBabel07101719252D 43 43 0 0 1 0 0 0 0 0999 V2000 -2.0261 -5.7485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3550 1.0093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1371 2.5547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5308 -0.7789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8351 -2.3650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4761 -0.7789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0567 -2.4838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0274 4.2886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3529 2.4593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8319 -5.1563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7219 -4.1623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8061 -3.7607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6961 -2.7667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7803 -2.3650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4077 2.4593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5274 -2.7455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2999 2.0078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7251 -1.3711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6703 -1.3711 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7924 -1.8066 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0274 3.2886 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4843 1.9124 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5705 1.9124 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4732 -2.4208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8093 -0.9694 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2455 -0.9694 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5816 -2.4208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0410 3.1240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8932 2.6481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0548 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0826 0.9966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5274 -2.7455 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0138 3.1240 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1616 2.6481 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.9722 0.9966 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.2623 -1.8066 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.9492 -3.3003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1056 -3.3003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7163 4.0698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5074 3.4372 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0514 -0.0826 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8868 1.2421 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 10 1 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 18 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 19 1 0 0 0 0 15 17 1 0 0 0 0 16 24 1 0 0 0 0 16 32 1 0 0 0 0 19 6 1 6 0 0 0 20 7 1 6 0 0 0 20 26 1 0 0 0 0 20 27 1 0 0 0 0 21 8 1 6 0 0 0 21 28 1 0 0 0 0 21 33 1 0 0 0 0 22 9 1 6 0 0 0 22 31 1 0 0 0 0 22 34 1 0 0 0 0 23 15 1 6 0 0 0 23 29 1 0 0 0 0 23 35 1 0 0 0 0 24 36 2 3 0 0 0 24 37 1 0 0 0 0 25 18 1 6 0 0 0 25 30 1 0 0 0 0 25 36 1 0 0 0 0 26 19 1 1 0 0 0 26 43 1 0 0 0 0 27 32 2 3 0 0 0 27 38 1 0 0 0 0 28 34 2 3 0 0 0 28 39 1 0 0 0 0 29 33 2 3 0 0 0 29 40 1 0 0 0 0 30 35 2 3 0 0 0 30 41 1 0 0 0 0 31 42 2 0 0 0 0 31 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	609.41
Volume:	636.872
LogP:	4.627
LogD:	4.367
LogS:	-4.379
# Rotatable Bonds:	9
TPSA:	171.8
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	1
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.196
Synthetic Accessibility Score:	5.171
Fsp3:	0.806
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.456
MDCK Permeability:	2.842272624548059e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.716
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.926
30% Bioavailability (F30%):	0.932

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	76.65878295898438%
Volume Distribution (VD):	0.561
Pgp-substrate:	5.246185302734375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.025
CYP2C19-inhibitor:	0.125
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.183
CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.629
CYP3A4-substrate:	0.122

ADMET: Excretion

Clearance (CL):	5.009
Half-life (T1/2):	0.515

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.963
Drug-inuced Liver Injury (DILI):	0.705
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.139
Carcinogencity:	0.03
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.786

Download Data

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

Natural Product: NPC43219

Natural Product ID:	NPC43219
*Common Name:**	Emericellamide A
IUPAC Name:	(3S,6S,9S,12S,18R,19R)-3,6,18-trimethyl-9-(2-methylpropyl)-19-[(2S)-octan-2-yl]-12-propan-2-yl-1-oxa-4,7,10,13,16-pentazacyclononadecane-2,5,8,11,14,17-hexone
Synonyms:
Standard InCHIKey:	QURRTAYEASAREY-OOVPVTRWSA-N
Standard InCHI:	InChI=1S/C31H55N5O7/c1-10-11-12-13-14-19(6)26-20(7)27(38)32-16-24(37)36-25(18(4)5)30(41)35-23(15-17(2)3)29(40)33-21(8)28(39)34-22(9)31(42)43-26/h17-23,25-26H,10-16H2,1-9H3,(H,32,38)(H,33,40)(H,34,39)(H,35,41)(H,36,37)/t19-,20+,21-,22-,23-,25-,26+/m0/s1
SMILES:	CCCCCC[C@@H]([C@H]1OC(=O)[C@H](C)N=C(O)[C@H](C)N=C(O)[C@@H](N=C([C@@H](N=C(CN=C([C@@H]1C)O)O)C(C)C)O)CC(C)C)C
Synthetic Gene Cluster:	BGC0001290;
ChEMBL Identifier:	CHEMBL225269
PubChem CID:	16216151
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO15076	Salinispora arenicola	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15916417]
NPO15076	Salinispora arenicola	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17253854]
NPO33058	emericella sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17323993]
NPO15076	Salinispora arenicola	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17323993]
NPO33058	emericella sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19013822]
NPO15076	Salinispora arenicola	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19117399]
NPO15076	Salinispora arenicola	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31313922]
NPO15076	Salinispora arenicola	Species	Micromonosporaceae	Bacteria	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
IC50	1
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	23000.0	nM	PMID[550747]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3800.0	nM	PMID[550747]

☑ 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 NPC43219 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	82
0.1-0.2	2728
0.2-0.3	21367
0.3-0.4	14056
0.4-0.5	3749
0.5-0.6	522
0.6-0.7	102
0.7-0.8	61
0.8-0.85	16
0.85-0.9	3
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9853	High Similarity	NPC86064
0.9265	High Similarity	NPC478256
0.8354	Intermediate Similarity	NPC227051
0.831	Intermediate Similarity	NPC474299
0.831	Intermediate Similarity	NPC473985
0.831	Intermediate Similarity	NPC474298
0.831	Intermediate Similarity	NPC475808
0.831	Intermediate Similarity	NPC28348
0.8228	Intermediate Similarity	NPC155670
0.8228	Intermediate Similarity	NPC95478
0.8228	Intermediate Similarity	NPC145748
0.8072	Intermediate Similarity	NPC477729
0.7973	Intermediate Similarity	NPC474403
0.7927	Intermediate Similarity	NPC477728
0.7922	Intermediate Similarity	NPC316242
0.7867	Intermediate Similarity	NPC138435
0.7821	Intermediate Similarity	NPC315535
0.7821	Intermediate Similarity	NPC315131
0.7821	Intermediate Similarity	NPC478017
0.7733	Intermediate Similarity	NPC141325
0.7703	Intermediate Similarity	NPC476291
0.7703	Intermediate Similarity	NPC476285
0.7671	Intermediate Similarity	NPC470110
0.7662	Intermediate Similarity	NPC476130
0.7662	Intermediate Similarity	NPC476324
0.7654	Intermediate Similarity	NPC477730
0.7534	Intermediate Similarity	NPC470109
0.7439	Intermediate Similarity	NPC47135
0.7403	Intermediate Similarity	NPC476248
0.7397	Intermediate Similarity	NPC470108
0.7375	Intermediate Similarity	NPC473984
0.7363	Intermediate Similarity	NPC220234
0.7333	Intermediate Similarity	NPC472579
0.7333	Intermediate Similarity	NPC314273
0.7333	Intermediate Similarity	NPC193280
0.72	Intermediate Similarity	NPC195165
0.7143	Intermediate Similarity	NPC477200
0.7125	Intermediate Similarity	NPC472594
0.7089	Intermediate Similarity	NPC472595
0.7083	Intermediate Similarity	NPC477644
0.7079	Intermediate Similarity	NPC270005
0.7079	Intermediate Similarity	NPC208537
0.7051	Intermediate Similarity	NPC477641
0.7051	Intermediate Similarity	NPC320865
0.7051	Intermediate Similarity	NPC477643
0.7024	Intermediate Similarity	NPC474312
0.7013	Intermediate Similarity	NPC477642
0.6988	Remote Similarity	NPC314466
0.6947	Remote Similarity	NPC124554
0.6947	Remote Similarity	NPC5864
0.6947	Remote Similarity	NPC301148
0.6933	Remote Similarity	NPC474402
0.6901	Remote Similarity	NPC472578
0.6883	Remote Similarity	NPC474812
0.6866	Remote Similarity	NPC329181
0.6866	Remote Similarity	NPC319110
0.6812	Remote Similarity	NPC270041
0.6804	Remote Similarity	NPC124549
0.6742	Remote Similarity	NPC193386
0.6739	Remote Similarity	NPC470283
0.6716	Remote Similarity	NPC80350
0.6712	Remote Similarity	NPC329564
0.6712	Remote Similarity	NPC327170
0.6703	Remote Similarity	NPC315237
0.6701	Remote Similarity	NPC198344
0.6667	Remote Similarity	NPC476523
0.6667	Remote Similarity	NPC145658
0.6627	Remote Similarity	NPC37681
0.66	Remote Similarity	NPC171734
0.66	Remote Similarity	NPC67009
0.6575	Remote Similarity	NPC316826
0.6575	Remote Similarity	NPC321468
0.6575	Remote Similarity	NPC473599
0.6575	Remote Similarity	NPC317143
0.6575	Remote Similarity	NPC327748
0.6552	Remote Similarity	NPC320936
0.6552	Remote Similarity	NPC323180
0.6548	Remote Similarity	NPC474833
0.6533	Remote Similarity	NPC145627
0.6528	Remote Similarity	NPC317147
0.6528	Remote Similarity	NPC318260
0.6522	Remote Similarity	NPC173763
0.6522	Remote Similarity	NPC62263
0.6522	Remote Similarity	NPC322946
0.6522	Remote Similarity	NPC471098
0.6486	Remote Similarity	NPC471129
0.6484	Remote Similarity	NPC475801
0.6484	Remote Similarity	NPC474593
0.6477	Remote Similarity	NPC175419
0.6452	Remote Similarity	NPC226513
0.6413	Remote Similarity	NPC474576
0.6381	Remote Similarity	NPC471645
0.6374	Remote Similarity	NPC322966
0.6374	Remote Similarity	NPC470284
0.6333	Remote Similarity	NPC171698
0.6333	Remote Similarity	NPC321340
0.6333	Remote Similarity	NPC270957
0.6333	Remote Similarity	NPC323958
0.6333	Remote Similarity	NPC119633
0.6322	Remote Similarity	NPC246005
0.6279	Remote Similarity	NPC474702
0.6267	Remote Similarity	NPC470363
0.6238	Remote Similarity	NPC475918
0.6197	Remote Similarity	NPC137327
0.6176	Remote Similarity	NPC319709
0.6176	Remote Similarity	NPC289484
0.6139	Remote Similarity	NPC205176
0.6139	Remote Similarity	NPC323720
0.6133	Remote Similarity	NPC254541
0.6133	Remote Similarity	NPC320598
0.6129	Remote Similarity	NPC159369
0.6129	Remote Similarity	NPC39290
0.6118	Remote Similarity	NPC330017
0.6111	Remote Similarity	NPC477199
0.6111	Remote Similarity	NPC321118
0.6111	Remote Similarity	NPC316889
0.6091	Remote Similarity	NPC310467
0.6082	Remote Similarity	NPC47076
0.6082	Remote Similarity	NPC134504
0.6076	Remote Similarity	NPC326651
0.6076	Remote Similarity	NPC325117
0.6076	Remote Similarity	NPC322319
0.6064	Remote Similarity	NPC476019
0.6064	Remote Similarity	NPC477538
0.6047	Remote Similarity	NPC473741
0.6047	Remote Similarity	NPC477145
0.6027	Remote Similarity	NPC471917
0.6024	Remote Similarity	NPC55274
0.6024	Remote Similarity	NPC315897
0.6	Remote Similarity	NPC169328
0.6	Remote Similarity	NPC189301
0.6	Remote Similarity	NPC477237
0.6	Remote Similarity	NPC176164
0.598	Remote Similarity	NPC14537
0.598	Remote Similarity	NPC74035
0.5977	Remote Similarity	NPC469492
0.5963	Remote Similarity	NPC201968
0.596	Remote Similarity	NPC475440
0.5955	Remote Similarity	NPC84128
0.5955	Remote Similarity	NPC53858
0.5952	Remote Similarity	NPC178919
0.5952	Remote Similarity	NPC263281
0.5949	Remote Similarity	NPC314103
0.5943	Remote Similarity	NPC476875
0.5922	Remote Similarity	NPC473252
0.5921	Remote Similarity	NPC321536
0.5918	Remote Similarity	NPC313821
0.5909	Remote Similarity	NPC469517
0.5905	Remote Similarity	NPC329305
0.5893	Remote Similarity	NPC477238
0.5875	Remote Similarity	NPC238646
0.5875	Remote Similarity	NPC476330
0.5862	Remote Similarity	NPC191774
0.5857	Remote Similarity	NPC87359
0.5857	Remote Similarity	NPC180402
0.5851	Remote Similarity	NPC292345
0.5843	Remote Similarity	NPC476302
0.5841	Remote Similarity	NPC45777
0.5841	Remote Similarity	NPC477061
0.5833	Remote Similarity	NPC273814
0.5833	Remote Similarity	NPC63191
0.5833	Remote Similarity	NPC471202
0.5824	Remote Similarity	NPC472351
0.5823	Remote Similarity	NPC316674
0.5823	Remote Similarity	NPC474552
0.5811	Remote Similarity	NPC322573
0.581	Remote Similarity	NPC15413
0.5804	Remote Similarity	NPC237420
0.58	Remote Similarity	NPC234542
0.58	Remote Similarity	NPC475758
0.5789	Remote Similarity	NPC328447
0.5784	Remote Similarity	NPC475149
0.5784	Remote Similarity	NPC471097
0.5784	Remote Similarity	NPC477198
0.5783	Remote Similarity	NPC45060
0.5783	Remote Similarity	NPC280065
0.578	Remote Similarity	NPC50694
0.578	Remote Similarity	NPC472536
0.578	Remote Similarity	NPC103391
0.5775	Remote Similarity	NPC328378
0.5769	Remote Similarity	NPC258130
0.5769	Remote Similarity	NPC475637
0.5769	Remote Similarity	NPC36497
0.5761	Remote Similarity	NPC277918
0.5758	Remote Similarity	NPC189629
0.5758	Remote Similarity	NPC473597
0.5758	Remote Similarity	NPC475503
0.5758	Remote Similarity	NPC123141
0.5753	Remote Similarity	NPC123814
0.5753	Remote Similarity	NPC474322
0.575	Remote Similarity	NPC41429
0.5743	Remote Similarity	NPC475791
0.5743	Remote Similarity	NPC13175
0.5743	Remote Similarity	NPC473224
0.5732	Remote Similarity	NPC469925
0.5732	Remote Similarity	NPC10716
0.573	Remote Similarity	NPC476137
0.573	Remote Similarity	NPC476156
0.573	Remote Similarity	NPC216090
0.573	Remote Similarity	NPC476117

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 NPC43219 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	64
0.1-0.2	1796
0.2-0.3	4771
0.3-0.4	1844
0.4-0.5	494
0.5-0.6	160
0.6-0.7	16
0.7-0.8	4
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.831	Intermediate Similarity	NPD3724	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7917	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7918	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD2263	Discontinued
0.7439	Intermediate Similarity	NPD7345	Approved
0.7108	Intermediate Similarity	NPD1448	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2256	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3187	Discontinued
0.6914	Remote Similarity	NPD2689	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1453	Phase 1
0.6627	Remote Similarity	NPD3160	Suspended
0.6625	Remote Similarity	NPD6944	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD8394	Approved
0.6556	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD9441	Phase 2
0.6452	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8144	Approved
0.6429	Remote Similarity	NPD8143	Approved
0.6404	Remote Similarity	NPD3723	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD2257	Approved
0.6364	Remote Similarity	NPD1831	Phase 3
0.6316	Remote Similarity	NPD7844	Discontinued
0.6214	Remote Similarity	NPD6413	Approved
0.6176	Remote Similarity	NPD3211	Approved
0.6173	Remote Similarity	NPD2694	Approved
0.6173	Remote Similarity	NPD2697	Approved
0.6173	Remote Similarity	NPD2696	Approved
0.6173	Remote Similarity	NPD2695	Approved
0.6129	Remote Similarity	NPD3716	Discontinued
0.6111	Remote Similarity	NPD9419	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4759	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD8305	Approved
0.6058	Remote Similarity	NPD8306	Approved
0.6056	Remote Similarity	NPD7348	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD1152	Phase 2
0.6027	Remote Similarity	NPD1830	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD364	Discontinued
0.6024	Remote Similarity	NPD1825	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD1147	Phase 2
0.6	Remote Similarity	NPD6699	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5380	Approved
0.6	Remote Similarity	NPD3733	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6421	Discontinued
0.5976	Remote Similarity	NPD3725	Approved
0.5976	Remote Similarity	NPD3726	Approved
0.5942	Remote Similarity	NPD379	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7916	Approved
0.5926	Remote Similarity	NPD7915	Approved
0.5918	Remote Similarity	NPD3190	Approved
0.5918	Remote Similarity	NPD3191	Approved
0.5918	Remote Similarity	NPD4228	Discovery
0.5918	Remote Similarity	NPD6428	Approved
0.5918	Remote Similarity	NPD3189	Approved
0.5909	Remote Similarity	NPD5354	Approved
0.59	Remote Similarity	NPD8418	Phase 2
0.5895	Remote Similarity	NPD6094	Approved
0.5895	Remote Similarity	NPD6095	Approved
0.5889	Remote Similarity	NPD4829	Discontinued
0.5862	Remote Similarity	NPD4278	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD1815	Discontinued
0.5851	Remote Similarity	NPD618	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8298	Phase 2
0.5811	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD9433	Approved
0.5789	Remote Similarity	NPD9661	Approved
0.5769	Remote Similarity	NPD574	Approved
0.5753	Remote Similarity	NPD3215	Phase 1
0.5729	Remote Similarity	NPD4780	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD8275	Approved
0.5728	Remote Similarity	NPD8276	Approved
0.5714	Remote Similarity	NPD7643	Phase 1
0.5714	Remote Similarity	NPD573	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8175	Discontinued
0.57	Remote Similarity	NPD3714	Approved
0.57	Remote Similarity	NPD3715	Approved
0.57	Remote Similarity	NPD3713	Approved
0.5696	Remote Similarity	NPD9676	Phase 3
0.5696	Remote Similarity	NPD575	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD7840	Approved
0.5663	Remote Similarity	NPD4242	Approved
0.566	Remote Similarity	NPD8174	Phase 2
0.5641	Remote Similarity	NPD3198	Approved
0.5631	Remote Similarity	NPD3184	Approved
0.5631	Remote Similarity	NPD3185	Approved
0.5631	Remote Similarity	NPD8083	Approved
0.5631	Remote Similarity	NPD3182	Approved
0.5631	Remote Similarity	NPD8084	Approved
0.5631	Remote Similarity	NPD8138	Approved
0.5631	Remote Similarity	NPD8082	Approved
0.5631	Remote Similarity	NPD3183	Approved
0.5631	Remote Similarity	NPD8086	Approved
0.5631	Remote Similarity	NPD8085	Approved
0.5631	Remote Similarity	NPD8139	Approved
0.5619	Remote Similarity	NPD8393	Approved
0.561	Remote Similarity	NPD1429	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD6941	Approved
0.56	Remote Similarity	NPD4276	Approved
0.56	Remote Similarity	NPD4277	Approved
0.56	Remote Similarity	NPD3730	Approved
0.56	Remote Similarity	NPD3728	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