NPASS Compound

Structure

NPC14877 OpenBabel07101718322D 45 47 0 0 1 0 0 0 0 0999 V2000 2.6942 -1.8801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4296 4.6932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6543 3.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5418 -0.7187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7140 4.5078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9842 -0.7187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2000 0.4971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2000 3.0231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9871 -1.1730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2459 -0.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0860 1.9456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7399 3.0356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7153 2.7227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3693 3.8127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4690 1.3249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6266 2.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6884 3.7273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 0.1723 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5575 3.5201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5302 0.1723 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0983 2.1020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3570 3.6563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0388 2.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4813 1.4813 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9813 3.0201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0388 1.4813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5302 3.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 3.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9813 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4813 2.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5575 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.5201 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8666 0.9511 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 2.3479 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 2.5691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.9863 4.4335 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0265 1.3249 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9842 4.2389 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6884 -0.2071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4690 2.1953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7140 -0.9877 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 2.0388 3.6569 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 7 36 1 0 0 0 0 8 37 1 0 0 0 0 9 10 1 0 0 0 0 11 13 1 0 0 0 0 11 21 2 0 0 0 0 12 14 2 0 0 0 0 12 21 1 0 0 0 0 13 22 2 0 0 0 0 14 22 1 0 0 0 0 15 21 1 0 0 0 0 16 24 2 0 0 0 0 16 45 1 0 0 0 0 18 4 1 1 0 0 0 18 23 1 0 0 0 0 18 32 1 0 0 0 0 19 5 1 1 0 0 0 19 29 1 0 0 0 0 19 33 1 0 0 0 0 20 6 1 1 0 0 0 20 30 1 0 0 0 0 20 44 1 0 0 0 0 22 38 1 0 0 0 0 23 10 1 6 0 0 0 23 34 1 0 0 0 0 24 27 1 0 0 0 0 24 35 1 0 0 0 0 25 15 1 1 0 0 0 25 31 1 0 0 0 0 25 36 1 0 0 0 0 26 17 1 1 0 0 0 26 28 1 0 0 0 0 26 37 1 0 0 0 0 27 34 2 3 0 0 0 27 39 1 0 0 0 0 28 33 2 3 0 0 0 28 40 1 0 0 0 0 29 35 2 0 0 0 0 29 45 1 0 0 0 0 30 36 1 0 0 0 0 30 41 2 0 0 0 0 31 37 1 0 0 0 0 31 42 2 0 0 0 0 32 43 2 0 0 0 0 32 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	643.3
Volume:	645.018
LogP:	3.892
LogD:	3.046
LogS:	-4.153
# Rotatable Bonds:	5
TPSA:	158.24
# H-Bond Aceptor:	12
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.42
Synthetic Accessibility Score:	5.834
Fsp3:	0.562
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:	-4.965
MDCK Permeability:	1.3547683010983746e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.979
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.707

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	70.05831146240234%
Volume Distribution (VD):	0.315
Pgp-substrate:	23.93137550354004%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.398
CYP2C19-substrate:	0.256
CYP2C9-inhibitor:	0.643
CYP2C9-substrate:	0.108
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.908
CYP3A4-substrate:	0.749

ADMET: Excretion

Clearance (CL):	5.36
Half-life (T1/2):	0.134

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.964
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.553
Skin Sensitization:	0.029
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.111

Download Data

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

Natural Product: NPC14877

Natural Product ID:	NPC14877
*Common Name:**	Ulongamide B
IUPAC Name:	(4R,5R,8S,11S,14S,17S)-11-[(4-hydroxyphenyl)methyl]-5,8,10,13,17-pentamethyl-14-propan-2-yl-4-propyl-7-oxa-19-thia-3,10,13,16,21-pentazabicyclo[16.2.1]henicosa-1(20),18(21)-diene-2,6,9,12,15-pentone
Synonyms:
Standard InCHIKey:	GGYQVLOCMGQKAQ-DUUHMJOYSA-N
Standard InCHI:	InChI=1S/C32H45N5O7S/c1-9-10-23-18(4)32(43)44-20(6)30(41)36(7)25(15-21-11-13-22(38)14-12-21)31(42)37(8)26(17(2)3)28(40)33-19(5)29-35-24(16-45-29)27(39)34-23/h11-14,16-20,23,25-26,38H,9-10,15H2,1-8H3,(H,33,40)(H,34,39)/t18-,19+,20+,23-,25+,26+/m1/s1
SMILES:	CCC[C@@H]1[C@@H](C)C(=O)O[C@@H](C)C(=O)N(C)[C@@H](Cc2ccc(cc2)O)C(=O)N(C)[C@@H](C(C)C)C(=N[C@@H](C)c2nc(cs2)C(=N1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503941
PubChem CID:	11093484
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
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	Palauan	n.a.	PMID[12141859]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12502348]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12762789]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	Palauan	n.a.	PMID[12762800]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14695793]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	Florida Everglades	n.a.	PMID[17432902]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18693761]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	Florida Keys	n.a.	PMID[21705224]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1000.0	nM	PMID[556246]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	5000.0	nM	PMID[556246]

☑ 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 NPC14877 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	262
0.1-0.2	1913
0.2-0.3	11441
0.3-0.4	9726
0.4-0.5	15701
0.5-0.6	3014
0.6-0.7	588
0.7-0.8	44
0.8-0.85	1
0.85-0.9	0
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC145178
1.0	High Similarity	NPC475350
0.984	High Similarity	NPC251036
0.9189	High Similarity	NPC165538
0.9081	High Similarity	NPC122427
0.9081	High Similarity	NPC329961
0.8224	Intermediate Similarity	NPC475196
0.8159	Intermediate Similarity	NPC75498
0.7681	Intermediate Similarity	NPC257511
0.7626	Intermediate Similarity	NPC96016
0.7525	Intermediate Similarity	NPC161143
0.7461	Intermediate Similarity	NPC24990
0.7415	Intermediate Similarity	NPC239660
0.7415	Intermediate Similarity	NPC106235
0.7411	Intermediate Similarity	NPC161242
0.7376	Intermediate Similarity	NPC329731
0.7376	Intermediate Similarity	NPC4910
0.7337	Intermediate Similarity	NPC229160
0.7337	Intermediate Similarity	NPC263485
0.7337	Intermediate Similarity	NPC25316
0.7323	Intermediate Similarity	NPC475534
0.7323	Intermediate Similarity	NPC476080
0.7286	Intermediate Similarity	NPC475330
0.725	Intermediate Similarity	NPC174652
0.7246	Intermediate Similarity	NPC184933
0.7246	Intermediate Similarity	NPC59827
0.7245	Intermediate Similarity	NPC476103
0.7227	Intermediate Similarity	NPC315804
0.7227	Intermediate Similarity	NPC313804
0.7184	Intermediate Similarity	NPC477526
0.7149	Intermediate Similarity	NPC323198
0.7149	Intermediate Similarity	NPC323752
0.7143	Intermediate Similarity	NPC477527
0.7136	Intermediate Similarity	NPC26108
0.7136	Intermediate Similarity	NPC279871
0.7085	Intermediate Similarity	NPC137627
0.7074	Intermediate Similarity	NPC105717
0.7056	Intermediate Similarity	NPC473502
0.7054	Intermediate Similarity	NPC478141
0.705	Intermediate Similarity	NPC326407
0.705	Intermediate Similarity	NPC318930
0.705	Intermediate Similarity	NPC317362
0.705	Intermediate Similarity	NPC317725
0.7041	Intermediate Similarity	NPC63931
0.7035	Intermediate Similarity	NPC319232
0.7035	Intermediate Similarity	NPC24370
0.703	Intermediate Similarity	NPC269750
0.703	Intermediate Similarity	NPC194671
0.7004	Intermediate Similarity	NPC304307
0.7004	Intermediate Similarity	NPC118559
0.7004	Intermediate Similarity	NPC34580
0.7004	Intermediate Similarity	NPC124920
0.7	Intermediate Similarity	NPC248670
0.6985	Remote Similarity	NPC475204
0.6985	Remote Similarity	NPC475123
0.6976	Remote Similarity	NPC471050
0.6976	Remote Similarity	NPC471048
0.6976	Remote Similarity	NPC294951
0.6976	Remote Similarity	NPC471049
0.6974	Remote Similarity	NPC100547
0.6968	Remote Similarity	NPC81026
0.6965	Remote Similarity	NPC471165
0.695	Remote Similarity	NPC89831
0.6946	Remote Similarity	NPC475421
0.6943	Remote Similarity	NPC95240
0.6943	Remote Similarity	NPC322135
0.6943	Remote Similarity	NPC223409
0.6931	Remote Similarity	NPC16188
0.693	Remote Similarity	NPC186351
0.693	Remote Similarity	NPC261251
0.6927	Remote Similarity	NPC286551
0.6915	Remote Similarity	NPC266741
0.6913	Remote Similarity	NPC469858
0.6913	Remote Similarity	NPC14288
0.6912	Remote Similarity	NPC249662
0.69	Remote Similarity	NPC196091
0.69	Remote Similarity	NPC40234
0.689	Remote Similarity	NPC473305
0.689	Remote Similarity	NPC163961
0.6886	Remote Similarity	NPC214142
0.6883	Remote Similarity	NPC54803
0.6883	Remote Similarity	NPC321592
0.6881	Remote Similarity	NPC158277
0.6881	Remote Similarity	NPC316403
0.6881	Remote Similarity	NPC476227
0.6875	Remote Similarity	NPC233702
0.6869	Remote Similarity	NPC472923
0.6853	Remote Similarity	NPC284888
0.6849	Remote Similarity	NPC478005
0.6845	Remote Similarity	NPC167763
0.6845	Remote Similarity	NPC470112
0.6845	Remote Similarity	NPC470903
0.6845	Remote Similarity	NPC263493
0.6845	Remote Similarity	NPC269398
0.6832	Remote Similarity	NPC306804
0.6825	Remote Similarity	NPC209509
0.6824	Remote Similarity	NPC33064
0.6824	Remote Similarity	NPC245055
0.6805	Remote Similarity	NPC316110
0.6805	Remote Similarity	NPC313587
0.6805	Remote Similarity	NPC315893
0.6804	Remote Similarity	NPC39431
0.68	Remote Similarity	NPC294516
0.68	Remote Similarity	NPC107938
0.6798	Remote Similarity	NPC159767
0.6798	Remote Similarity	NPC155506
0.6794	Remote Similarity	NPC238242
0.6779	Remote Similarity	NPC299806
0.6766	Remote Similarity	NPC315388
0.6765	Remote Similarity	NPC50016
0.6753	Remote Similarity	NPC262166
0.6753	Remote Similarity	NPC202198
0.675	Remote Similarity	NPC254700
0.6749	Remote Similarity	NPC273755
0.6748	Remote Similarity	NPC153554
0.6738	Remote Similarity	NPC470884
0.6738	Remote Similarity	NPC178662
0.6738	Remote Similarity	NPC476133
0.6738	Remote Similarity	NPC92784
0.6738	Remote Similarity	NPC98424
0.6737	Remote Similarity	NPC82472
0.6736	Remote Similarity	NPC473491
0.6734	Remote Similarity	NPC133470
0.6734	Remote Similarity	NPC191863
0.6734	Remote Similarity	NPC289776
0.6716	Remote Similarity	NPC473354
0.6714	Remote Similarity	NPC94862
0.6701	Remote Similarity	NPC323336
0.6701	Remote Similarity	NPC326349
0.67	Remote Similarity	NPC230611
0.6684	Remote Similarity	NPC471265
0.6684	Remote Similarity	NPC471264
0.6683	Remote Similarity	NPC186617
0.6667	Remote Similarity	NPC83790
0.6667	Remote Similarity	NPC319751
0.6667	Remote Similarity	NPC128237
0.6667	Remote Similarity	NPC61004
0.6667	Remote Similarity	NPC476989
0.665	Remote Similarity	NPC471568
0.665	Remote Similarity	NPC46009
0.665	Remote Similarity	NPC473693
0.6639	Remote Similarity	NPC477590
0.6639	Remote Similarity	NPC477585
0.6639	Remote Similarity	NPC477586
0.6639	Remote Similarity	NPC477588
0.6638	Remote Similarity	NPC220852
0.6636	Remote Similarity	NPC328763
0.6635	Remote Similarity	NPC477637
0.6635	Remote Similarity	NPC476321
0.6634	Remote Similarity	NPC473402
0.6633	Remote Similarity	NPC469243
0.6618	Remote Similarity	NPC45037
0.6604	Remote Similarity	NPC188104
0.6603	Remote Similarity	NPC471526
0.66	Remote Similarity	NPC241794
0.6599	Remote Similarity	NPC476268
0.6599	Remote Similarity	NPC473580
0.6598	Remote Similarity	NPC283783
0.6596	Remote Similarity	NPC477516
0.659	Remote Similarity	NPC323662
0.6582	Remote Similarity	NPC5194
0.6582	Remote Similarity	NPC56685
0.6582	Remote Similarity	NPC261934
0.658	Remote Similarity	NPC329761
0.658	Remote Similarity	NPC225648
0.6573	Remote Similarity	NPC240130
0.6573	Remote Similarity	NPC61332
0.6564	Remote Similarity	NPC119481
0.6564	Remote Similarity	NPC74969
0.6562	Remote Similarity	NPC5620
0.656	Remote Similarity	NPC140284
0.656	Remote Similarity	NPC75609
0.6555	Remote Similarity	NPC477589
0.6555	Remote Similarity	NPC477587
0.6555	Remote Similarity	NPC285343
0.6553	Remote Similarity	NPC136797
0.6552	Remote Similarity	NPC302597
0.6552	Remote Similarity	NPC209463
0.655	Remote Similarity	NPC475544
0.6545	Remote Similarity	NPC139326
0.6535	Remote Similarity	NPC223207
0.6532	Remote Similarity	NPC472286
0.6532	Remote Similarity	NPC472287
0.6528	Remote Similarity	NPC477632
0.6528	Remote Similarity	NPC477638
0.6522	Remote Similarity	NPC478007
0.652	Remote Similarity	NPC280022
0.6515	Remote Similarity	NPC244509
0.6514	Remote Similarity	NPC472284
0.6513	Remote Similarity	NPC473398
0.6508	Remote Similarity	NPC6570
0.6508	Remote Similarity	NPC314056
0.6504	Remote Similarity	NPC153400
0.6502	Remote Similarity	NPC304074
0.6502	Remote Similarity	NPC290755
0.6502	Remote Similarity	NPC471771
0.65	Remote Similarity	NPC244336
0.6495	Remote Similarity	NPC145113
0.6481	Remote Similarity	NPC302715
0.6477	Remote Similarity	NPC322878

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 NPC14877 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	490
0.2-0.3	907
0.3-0.4	1570
0.4-0.5	3801
0.5-0.6	2001
0.6-0.7	217
0.7-0.8	3
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
0.7415	Intermediate Similarity	NPD8339	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4652	Approved
0.7054	Intermediate Similarity	NPD8356	Approved
0.7053	Intermediate Similarity	NPD6348	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2098	Approved
0.7039	Intermediate Similarity	NPD6632	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD3879	Approved
0.6939	Remote Similarity	NPD2097	Approved
0.693	Remote Similarity	NPD8430	Approved
0.6923	Remote Similarity	NPD6349	Phase 1
0.6909	Remote Similarity	NPD3878	Approved
0.6891	Remote Similarity	NPD3328	Phase 2
0.6863	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5994	Discontinued
0.6835	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5114	Approved
0.681	Remote Similarity	NPD5112	Approved
0.681	Remote Similarity	NPD5113	Approved
0.6802	Remote Similarity	NPD5452	Phase 2
0.6786	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2888	Approved
0.6766	Remote Similarity	NPD2890	Approved
0.6766	Remote Similarity	NPD2017	Approved
0.6766	Remote Similarity	NPD2889	Approved
0.6763	Remote Similarity	NPD7977	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD8255	Phase 2
0.6729	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD4742	Phase 3
0.6712	Remote Similarity	NPD2853	Approved
0.6712	Remote Similarity	NPD4741	Phase 3
0.6701	Remote Similarity	NPD6390	Discontinued
0.6699	Remote Similarity	NPD5484	Approved
0.6699	Remote Similarity	NPD5485	Approved
0.6695	Remote Similarity	NPD7806	Phase 2
0.6681	Remote Similarity	NPD1976	Approved
0.668	Remote Similarity	NPD8107	Approved
0.6667	Remote Similarity	NPD8108	Approved
0.6637	Remote Similarity	NPD5191	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD3351	Approved
0.6615	Remote Similarity	NPD7303	Discontinued
0.6612	Remote Similarity	NPD6205	Discontinued
0.661	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7131	Phase 3
0.6577	Remote Similarity	NPD3350	Approved
0.6576	Remote Similarity	NPD6627	Discontinued
0.6575	Remote Similarity	NPD6256	Approved
0.6575	Remote Similarity	NPD6254	Approved
0.6575	Remote Similarity	NPD6255	Approved
0.6571	Remote Similarity	NPD5857	Phase 3
0.6562	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6475	Phase 2
0.6542	Remote Similarity	NPD6505	Approved
0.6542	Remote Similarity	NPD6504	Approved
0.654	Remote Similarity	NPD3074	Discontinued
0.6538	Remote Similarity	NPD2957	Phase 2
0.6534	Remote Similarity	NPD4884	Discovery
0.6533	Remote Similarity	NPD2513	Approved
0.653	Remote Similarity	NPD6253	Approved
0.6526	Remote Similarity	NPD4435	Approved
0.6515	Remote Similarity	NPD5189	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD8284	Discontinued
0.6507	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD8071	Approved
0.65	Remote Similarity	NPD3007	Approved
0.65	Remote Similarity	NPD2515	Approved
0.6498	Remote Similarity	NPD6347	Phase 2
0.6488	Remote Similarity	NPD2517	Approved
0.6479	Remote Similarity	NPD4434	Approved
0.6468	Remote Similarity	NPD8253	Phase 3
0.6466	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD7655	Discontinued
0.645	Remote Similarity	NPD5634	Approved
0.6441	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6888	Discontinued
0.644	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.644	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD2516	Approved
0.6435	Remote Similarity	NPD3479	Discontinued
0.6432	Remote Similarity	NPD2052	Approved
0.6426	Remote Similarity	NPD8292	Phase 2
0.6422	Remote Similarity	NPD8303	Discontinued
0.6419	Remote Similarity	NPD7496	Phase 2
0.6413	Remote Similarity	NPD5055	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6751	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4331	Approved
0.6404	Remote Similarity	NPD6188	Approved
0.6404	Remote Similarity	NPD6189	Approved
0.6402	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.64	Remote Similarity	NPD22	Approved
0.64	Remote Similarity	NPD2053	Approved
0.6398	Remote Similarity	NPD2852	Approved
0.6395	Remote Similarity	NPD8061	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7490	Discontinued
0.639	Remote Similarity	NPD7133	Discontinued
0.6389	Remote Similarity	NPD4949	Discontinued
0.6386	Remote Similarity	NPD4557	Approved
0.6384	Remote Similarity	NPD6551	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD4646	Approved
0.6382	Remote Similarity	NPD4648	Approved
0.6382	Remote Similarity	NPD4647	Approved
0.638	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD4897	Phase 2
0.6373	Remote Similarity	NPD2022	Approved
0.6368	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6367	Remote Similarity	NPD5817	Discontinued
0.6364	Remote Similarity	NPD4125	Approved
0.6364	Remote Similarity	NPD5638	Approved
0.636	Remote Similarity	NPD6187	Approved
0.6354	Remote Similarity	NPD3480	Approved
0.6345	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.634	Remote Similarity	NPD2436	Approved
0.634	Remote Similarity	NPD2437	Approved
0.633	Remote Similarity	NPD2046	Approved
0.633	Remote Similarity	NPD2048	Approved
0.633	Remote Similarity	NPD2045	Approved
0.633	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.633	Remote Similarity	NPD2047	Approved
0.633	Remote Similarity	NPD2043	Approved
0.633	Remote Similarity	NPD2044	Approved
0.633	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.633	Remote Similarity	NPD2051	Approved
0.633	Remote Similarity	NPD21	Approved
0.6327	Remote Similarity	NPD8260	Approved
0.632	Remote Similarity	NPD5453	Phase 2
0.6318	Remote Similarity	NPD2891	Approved
0.6316	Remote Similarity	NPD5323	Approved
0.6314	Remote Similarity	NPD7711	Discontinued
0.6313	Remote Similarity	NPD5076	Approved
0.6313	Remote Similarity	NPD5077	Approved
0.6309	Remote Similarity	NPD7180	Phase 3
0.6309	Remote Similarity	NPD3308	Approved
0.6308	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD7853	Phase 2
0.6301	Remote Similarity	NPD3396	Approved
0.6301	Remote Similarity	NPD3395	Approved
0.6296	Remote Similarity	NPD3335	Approved
0.629	Remote Similarity	NPD7873	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD2087	Approved
0.6289	Remote Similarity	NPD2088	Approved
0.6282	Remote Similarity	NPD6796	Discontinued
0.6281	Remote Similarity	NPD5230	Approved
0.6281	Remote Similarity	NPD5229	Approved
0.6279	Remote Similarity	NPD3334	Approved
0.6275	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6276	Discontinued
0.6272	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD3307	Approved
0.6263	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD6857	Phase 3
0.626	Remote Similarity	NPD7967	Discontinued
0.6255	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6255	Remote Similarity	NPD8247	Approved
0.6255	Remote Similarity	NPD8246	Approved
0.6245	Remote Similarity	NPD8116	Phase 3
0.6245	Remote Similarity	NPD8117	Approved
0.6245	Remote Similarity	NPD5640	Discontinued
0.6239	Remote Similarity	NPD6659	Phase 2
0.6238	Remote Similarity	NPD6915	Approved
0.6238	Remote Similarity	NPD2020	Approved
0.6235	Remote Similarity	NPD8359	Phase 2
0.6225	Remote Similarity	NPD8101	Phase 3
0.6224	Remote Similarity	NPD4460	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD7692	Discontinued
0.6222	Remote Similarity	NPD6324	Phase 1
0.6221	Remote Similarity	NPD5852	Approved
0.6221	Remote Similarity	NPD5851	Approved
0.6215	Remote Similarity	NPD8370	Discontinued
0.6213	Remote Similarity	NPD5506	Approved
0.6213	Remote Similarity	NPD5507	Approved
0.6212	Remote Similarity	NPD1979	Approved
0.6211	Remote Similarity	NPD5299	Approved
0.621	Remote Similarity	NPD7868	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7613	Discontinued
0.6195	Remote Similarity	NPD4903	Approved
0.6195	Remote Similarity	NPD4905	Approved
0.6195	Remote Similarity	NPD8272	Phase 2
0.6195	Remote Similarity	NPD7737	Approved
0.6195	Remote Similarity	NPD4906	Approved
0.6195	Remote Similarity	NPD7738	Approved
0.6188	Remote Similarity	NPD2019	Approved
0.6188	Remote Similarity	NPD2018	Approved
0.6186	Remote Similarity	NPD3275	Approved
0.6186	Remote Similarity	NPD3271	Approved
0.6183	Remote Similarity	NPD7796	Approved
0.6183	Remote Similarity	NPD7797	Approved
0.6181	Remote Similarity	NPD5613	Approved
0.6181	Remote Similarity	NPD2016	Approved
0.6181	Remote Similarity	NPD2014	Approved
0.6181	Remote Similarity	NPD5614	Approved
0.6181	Remote Similarity	NPD3988	Approved
0.6181	Remote Similarity	NPD2013	Approved
0.6181	Remote Similarity	NPD3987	Approved
0.6181	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7603	Discontinued
0.6175	Remote Similarity	NPD6891	Phase 2
0.6174	Remote Similarity	NPD7468	Clinical (unspecified phase)

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