NPASS Compound

Structure

NPC471771 OpenBabel07101719182D 67 70 0 0 1 0 0 0 0 0999 V2000 -0.4635 3.4776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4770 -5.6608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8894 4.5336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1513 -4.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9996 0.0276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1992 4.1548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4219 -4.6623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0456 0.3335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7471 1.2879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0180 -0.6661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8026 -5.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8284 -3.6595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6178 2.0334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0105 3.6554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9975 0.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1315 2.3974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1069 -3.4689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9094 2.3185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6084 -5.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6342 -4.2517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5543 2.3840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9470 4.0061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8635 1.3974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9975 2.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2169 -2.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7448 1.3321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1548 2.0937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2655 0.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1536 3.8563 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2590 -4.1153 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9126 -4.0612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8459 2.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1315 1.3974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5242 -5.2456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7189 3.3704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8635 2.3974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6674 -1.6026 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5889 -1.8828 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2655 -0.1026 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.1917 0.9815 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3723 2.8805 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2040 -3.1169 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0317 -2.3745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6917 1.8475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3708 2.9356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2100 -3.0068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1374 -0.9905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1315 -0.6026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3994 -1.6026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3331 2.6635 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3057 -2.5801 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.5334 -2.1026 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.3994 -0.6026 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.1798 -2.8982 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4458 2.5042 0.0000 N 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 3.3299 -5.8379 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6554 3.7210 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.7296 2.8974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6884 -3.1286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0802 2.4832 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4808 3.9296 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9379 -3.9691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8171 -1.2890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9975 -0.1026 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1315 -1.6026 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2655 -2.1026 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 5 56 1 0 0 0 0 6 29 1 0 0 0 0 7 30 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 27 1 0 0 0 0 10 37 1 0 0 0 0 11 19 1 0 0 0 0 11 31 2 0 0 0 0 12 20 2 0 0 0 0 12 31 1 0 0 0 0 13 21 1 0 0 0 0 13 32 2 0 0 0 0 14 22 2 0 0 0 0 14 32 1 0 0 0 0 15 23 1 0 0 0 0 15 33 2 0 0 0 0 16 24 2 0 0 0 0 16 33 1 0 0 0 0 17 25 1 0 0 0 0 17 31 1 0 0 0 0 18 26 1 0 0 0 0 18 32 1 0 0 0 0 19 34 2 0 0 0 0 20 34 1 0 0 0 0 21 35 2 0 0 0 0 22 35 1 0 0 0 0 23 36 2 0 0 0 0 24 36 1 0 0 0 0 27 50 1 0 0 0 0 28 33 1 0 0 0 0 28 39 1 0 0 0 0 29 3 1 1 0 0 0 30 4 1 6 0 0 0 34 57 1 0 0 0 0 35 58 1 0 0 0 0 36 59 1 0 0 0 0 37 43 1 0 0 0 0 37 52 1 6 0 0 0 38 25 1 6 0 0 0 38 47 1 0 0 0 0 38 51 1 0 0 0 0 39 48 1 0 0 0 0 39 53 1 0 0 0 0 40 26 1 6 0 0 0 40 44 1 0 0 0 0 40 56 1 0 0 0 0 41 29 1 6 0 0 0 41 45 1 0 0 0 0 41 55 1 0 0 0 0 42 30 1 6 0 0 0 42 46 1 0 0 0 0 42 54 1 0 0 0 0 43 54 2 3 0 0 0 43 60 1 0 0 0 0 44 55 2 3 0 0 0 44 61 1 0 0 0 0 45 50 2 3 0 0 0 45 62 1 0 0 0 0 46 51 2 3 0 0 0 46 63 1 0 0 0 0 47 56 1 0 0 0 0 47 64 2 0 0 0 0 48 65 2 0 0 0 0 48 66 1 0 0 0 0 49 52 2 3 0 0 0 49 53 1 0 0 0 0 49 67 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	929.49
Volume:	953.32
LogP:	3.999
LogD:	3.187
LogS:	-4.018
# Rotatable Bonds:	17
TPSA:	279.32
# H-Bond Aceptor:	18
# H-Bond Donor:	10
# Rings:	4
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.103
Synthetic Accessibility Score:	5.763
Fsp3:	0.49
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:	-6.443
MDCK Permeability:	3.420345819904469e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.855
20% Bioavailability (F20%):	0.986
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	90.54401397705078%
Volume Distribution (VD):	0.384
Pgp-substrate:	2.605477809906006%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.006
CYP2C19-inhibitor:	0.151
CYP2C19-substrate:	0.036
CYP2C9-inhibitor:	0.614
CYP2C9-substrate:	0.971
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.218
CYP3A4-inhibitor:	0.536
CYP3A4-substrate:	0.009

ADMET: Excretion

Clearance (CL):	2.504
Half-life (T1/2):	0.918

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.967
Drug-inuced Liver Injury (DILI):	0.898
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.742
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.044
Carcinogencity:	0.059
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.091

Download Data

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

Natural Product: NPC471771

Natural Product ID:	NPC471771
*Common Name:**	2-(3-{3,12-Di-Sec-Butyl-6,9-Bis-[2-(4-Hydroxy-Phenyl)-Ethyl]-7-Methyl-2,5,8,11,14-Pentaoxo-1,4,7,10,13Pentaaza-Cyclononadec-15-Yl}-Ureido)-3-(4-Hydroxy-Phenyl)-Propionic Acid
IUPAC Name:	2-[[(3S,6S,9S,12S,15R)-3,12-bis[(2S)-butan-2-yl]-6,9-bis[2-(4-hydroxyphenyl)ethyl]-7-methyl-2,5,8,11,14-pentaoxo-1,4,7,10,13-pentazacyclononadec-15-yl]carbamoylamino]-3-(4-hydroxyphenyl)propanoic acid
Synonyms:
Standard InCHIKey:	HXYYQLNMRLHXGK-RYYJQIQOSA-N
Standard InCHI:	InChI=1S/C49H67N7O11/c1-6-29(3)41-45(62)50-27-9-8-10-37(52-49(67)53-39(48(65)66)28-33-15-23-36(59)24-16-33)43(60)54-42(30(4)7-2)46(63)51-38(25-17-31-11-19-34(57)20-12-31)47(64)56(5)40(44(61)55-41)26-18-32-13-21-35(58)22-14-32/h11-16,19-24,29-30,37-42,57-59H,6-10,17-18,25-28H2,1-5H3,(H,50,62)(H,51,63)(H,54,60)(H,55,61)(H,65,66)(H2,52,53,67)/t29-,30-,37+,38-,39?,40-,41-,42-/m0/s1
SMILES:	CC[C@@H]([C@@H]1N=C(O)[C@@H](CCCCN=C([C@@H](N=C([C@@H](N(C(=O)[C@@H](N=C1O)CCc1ccc(cc1)O)C)CCc1ccc(cc1)O)O)[C@H](CC)C)O)N=C(NC(C(=O)O)Cc1ccc(cc1)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3143512
PubChem CID:	90663500
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO32547.3	oscillatoria agardhii	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10340607]

☑ 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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	0.0018	ug.mL-1	PMID[478033]

☑ 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 NPC471771 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	210
0.1-0.2	1073
0.2-0.3	6672
0.3-0.4	10849
0.4-0.5	15269
0.5-0.6	7445
0.6-0.7	830
0.7-0.8	287
0.8-0.85	42
0.85-0.9	8
0.9-0.95	5
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC304074
1.0	High Similarity	NPC290755
0.9933	High Similarity	NPC223207
0.9733	High Similarity	NPC469243
0.9733	High Similarity	NPC475544
0.9554	High Similarity	NPC196243
0.9467	High Similarity	NPC473580
0.9299	High Similarity	NPC274198
0.9299	High Similarity	NPC276506
0.9299	High Similarity	NPC198254
0.8788	High Similarity	NPC153554
0.8766	High Similarity	NPC233702
0.8571	High Similarity	NPC63931
0.8533	High Similarity	NPC132636
0.8485	Intermediate Similarity	NPC475532
0.8466	Intermediate Similarity	NPC328649
0.8434	Intermediate Similarity	NPC165285
0.8387	Intermediate Similarity	NPC16188
0.8382	Intermediate Similarity	NPC240130
0.8382	Intermediate Similarity	NPC61332
0.8372	Intermediate Similarity	NPC94862
0.8303	Intermediate Similarity	NPC280022
0.8303	Intermediate Similarity	NPC129486
0.8284	Intermediate Similarity	NPC97526
0.8284	Intermediate Similarity	NPC119652
0.8267	Intermediate Similarity	NPC244866
0.8263	Intermediate Similarity	NPC306804
0.8239	Intermediate Similarity	NPC302715
0.8239	Intermediate Similarity	NPC202198
0.8214	Intermediate Similarity	NPC155506
0.8214	Intermediate Similarity	NPC17698
0.8214	Intermediate Similarity	NPC159767
0.82	Intermediate Similarity	NPC326966
0.8187	Intermediate Similarity	NPC473404
0.8182	Intermediate Similarity	NPC61004
0.8133	Intermediate Similarity	NPC141957
0.811	Intermediate Similarity	NPC241794
0.8095	Intermediate Similarity	NPC89831
0.8095	Intermediate Similarity	NPC230611
0.807	Intermediate Similarity	NPC269750
0.807	Intermediate Similarity	NPC194671
0.807	Intermediate Similarity	NPC45037
0.8067	Intermediate Similarity	NPC325651
0.8065	Intermediate Similarity	NPC476989
0.8047	Intermediate Similarity	NPC248670
0.8047	Intermediate Similarity	NPC137627
0.8047	Intermediate Similarity	NPC273755
0.8036	Intermediate Similarity	NPC46009
0.8024	Intermediate Similarity	NPC107938
0.8024	Intermediate Similarity	NPC294516
0.8024	Intermediate Similarity	NPC209463
0.8	Intermediate Similarity	NPC473402
0.8	Intermediate Similarity	NPC279871
0.8	Intermediate Similarity	NPC158277
0.8	Intermediate Similarity	NPC476227
0.7989	Intermediate Similarity	NPC294951
0.7988	Intermediate Similarity	NPC319320
0.7988	Intermediate Similarity	NPC287757
0.7961	Intermediate Similarity	NPC257390
0.7953	Intermediate Similarity	NPC50016
0.7929	Intermediate Similarity	NPC40234
0.791	Intermediate Similarity	NPC102959
0.7901	Intermediate Similarity	NPC56685
0.7895	Intermediate Similarity	NPC473354
0.7895	Intermediate Similarity	NPC26108
0.7888	Intermediate Similarity	NPC473491
0.7885	Intermediate Similarity	NPC48202
0.7867	Intermediate Similarity	NPC477937
0.7865	Intermediate Similarity	NPC60516
0.7862	Intermediate Similarity	NPC81026
0.7861	Intermediate Similarity	NPC478005
0.7844	Intermediate Similarity	NPC191863
0.7844	Intermediate Similarity	NPC133470
0.7844	Intermediate Similarity	NPC289776
0.7829	Intermediate Similarity	NPC471526
0.7824	Intermediate Similarity	NPC475123
0.7824	Intermediate Similarity	NPC475204
0.7799	Intermediate Similarity	NPC266741
0.7791	Intermediate Similarity	NPC471165
0.7791	Intermediate Similarity	NPC136797
0.7791	Intermediate Similarity	NPC5194
0.7791	Intermediate Similarity	NPC261934
0.7791	Intermediate Similarity	NPC262166
0.779	Intermediate Similarity	NPC477632
0.779	Intermediate Similarity	NPC477638
0.7771	Intermediate Similarity	NPC244336
0.7765	Intermediate Similarity	NPC163961
0.7765	Intermediate Similarity	NPC473305
0.776	Intermediate Similarity	NPC477552
0.776	Intermediate Similarity	NPC477550
0.774	Intermediate Similarity	NPC138083
0.7714	Intermediate Similarity	NPC32064
0.7711	Intermediate Similarity	NPC323336
0.7711	Intermediate Similarity	NPC326349
0.7709	Intermediate Similarity	NPC234069
0.7707	Intermediate Similarity	NPC242159
0.7707	Intermediate Similarity	NPC313694
0.7702	Intermediate Similarity	NPC311658
0.7688	Intermediate Similarity	NPC164608
0.7676	Intermediate Similarity	NPC477551
0.767	Intermediate Similarity	NPC476321
0.7669	Intermediate Similarity	NPC324081
0.7667	Intermediate Similarity	NPC174122
0.7667	Intermediate Similarity	NPC64140
0.765	Intermediate Similarity	NPC477639
0.764	Intermediate Similarity	NPC299806
0.7636	Intermediate Similarity	NPC39431
0.7628	Intermediate Similarity	NPC267237
0.7602	Intermediate Similarity	NPC302597
0.76	Intermediate Similarity	NPC27581
0.759	Intermediate Similarity	NPC244509
0.759	Intermediate Similarity	NPC476268
0.7584	Intermediate Similarity	NPC471049
0.7584	Intermediate Similarity	NPC471048
0.7584	Intermediate Similarity	NPC471050
0.7569	Intermediate Similarity	NPC477636
0.7562	Intermediate Similarity	NPC168861
0.7558	Intermediate Similarity	NPC66490
0.7554	Intermediate Similarity	NPC329295
0.7533	Intermediate Similarity	NPC71684
0.7532	Intermediate Similarity	NPC111428
0.7532	Intermediate Similarity	NPC473322
0.7527	Intermediate Similarity	NPC473378
0.7527	Intermediate Similarity	NPC473407
0.7514	Intermediate Similarity	NPC170302
0.7514	Intermediate Similarity	NPC475409
0.7514	Intermediate Similarity	NPC475564
0.75	Intermediate Similarity	NPC276120
0.7487	Intermediate Similarity	NPC469443
0.7486	Intermediate Similarity	NPC477631
0.7485	Intermediate Similarity	NPC472923
0.7472	Intermediate Similarity	NPC477637
0.7453	Intermediate Similarity	NPC91953
0.7446	Intermediate Similarity	NPC328763
0.7438	Intermediate Similarity	NPC214988
0.7436	Intermediate Similarity	NPC255447
0.7424	Intermediate Similarity	NPC478007
0.7419	Intermediate Similarity	NPC296712
0.7414	Intermediate Similarity	NPC196091
0.7401	Intermediate Similarity	NPC473546
0.74	Intermediate Similarity	NPC319950
0.74	Intermediate Similarity	NPC283760
0.7399	Intermediate Similarity	NPC473502
0.7396	Intermediate Similarity	NPC56635
0.7394	Intermediate Similarity	NPC473450
0.7391	Intermediate Similarity	NPC197921
0.7377	Intermediate Similarity	NPC29531
0.7372	Intermediate Similarity	NPC478147
0.7363	Intermediate Similarity	NPC96275
0.736	Intermediate Similarity	NPC475421
0.7356	Intermediate Similarity	NPC186617
0.735	Intermediate Similarity	NPC478008
0.7348	Intermediate Similarity	NPC315542
0.7346	Intermediate Similarity	NPC469360
0.7333	Intermediate Similarity	NPC9373
0.7333	Intermediate Similarity	NPC470546
0.7317	Intermediate Similarity	NPC314114
0.7314	Intermediate Similarity	NPC473693
0.7314	Intermediate Similarity	NPC471568
0.7312	Intermediate Similarity	NPC6570
0.7312	Intermediate Similarity	NPC127741
0.7287	Intermediate Similarity	NPC323662
0.7283	Intermediate Similarity	NPC51047
0.7278	Intermediate Similarity	NPC45191
0.7273	Intermediate Similarity	NPC328494
0.7267	Intermediate Similarity	NPC470545
0.7262	Intermediate Similarity	NPC473341
0.7257	Intermediate Similarity	NPC315388
0.7254	Intermediate Similarity	NPC220060
0.7238	Intermediate Similarity	NPC470903
0.7238	Intermediate Similarity	NPC470112
0.7238	Intermediate Similarity	NPC167763
0.7234	Intermediate Similarity	NPC471592
0.7226	Intermediate Similarity	NPC101719
0.7219	Intermediate Similarity	NPC471563
0.7216	Intermediate Similarity	NPC469444
0.7215	Intermediate Similarity	NPC120251
0.7205	Intermediate Similarity	NPC6913
0.72	Intermediate Similarity	NPC106551
0.72	Intermediate Similarity	NPC281686
0.72	Intermediate Similarity	NPC470544
0.72	Intermediate Similarity	NPC188867
0.7196	Intermediate Similarity	NPC50548
0.7186	Intermediate Similarity	NPC254798
0.7184	Intermediate Similarity	NPC189116
0.7176	Intermediate Similarity	NPC469903
0.7166	Intermediate Similarity	NPC65714
0.7166	Intermediate Similarity	NPC314083
0.7161	Intermediate Similarity	NPC222466
0.7158	Intermediate Similarity	NPC235194
0.7151	Intermediate Similarity	NPC1390
0.7151	Intermediate Similarity	NPC62104
0.7151	Intermediate Similarity	NPC248822
0.7143	Intermediate Similarity	NPC314835
0.7143	Intermediate Similarity	NPC473360
0.7143	Intermediate Similarity	NPC144314
0.7143	Intermediate Similarity	NPC142577
0.7143	Intermediate Similarity	NPC474862
0.7143	Intermediate Similarity	NPC254700
0.7135	Intermediate Similarity	NPC246591

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 NPC471771 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	131
0.1-0.2	383
0.2-0.3	804
0.3-0.4	1465
0.4-0.5	3217
0.5-0.6	2526
0.6-0.7	570
0.7-0.8	49
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8553	High Similarity	NPD7495	Discontinued
0.8553	High Similarity	NPD8019	Approved
0.8519	High Similarity	NPD8303	Discontinued
0.8301	Intermediate Similarity	NPD7450	Phase 2
0.8125	Intermediate Similarity	NPD7523	Phase 3
0.784	Intermediate Similarity	NPD7303	Discontinued
0.7818	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD3136	Phase 2
0.7658	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7451	Discontinued
0.7569	Intermediate Similarity	NPD7617	Discontinued
0.7562	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7608	Discontinued
0.75	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7131	Phase 3
0.7457	Intermediate Similarity	NPD7484	Phase 3
0.7457	Intermediate Similarity	NPD7485	Phase 3
0.7453	Intermediate Similarity	NPD7978	Discontinued
0.7453	Intermediate Similarity	NPD8076	Discontinued
0.7444	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD4652	Approved
0.7386	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4677	Discontinued
0.7384	Intermediate Similarity	NPD2098	Approved
0.7375	Intermediate Similarity	NPD6901	Phase 3
0.7349	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6346	Approved
0.7267	Intermediate Similarity	NPD2097	Approved
0.7257	Intermediate Similarity	NPD2017	Approved
0.7257	Intermediate Similarity	NPD2890	Approved
0.7257	Intermediate Similarity	NPD2889	Approved
0.7257	Intermediate Similarity	NPD2888	Approved
0.7244	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6297	Approved
0.7215	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD9568	Approved
0.7175	Intermediate Similarity	NPD5137	Approved
0.7171	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5581	Approved
0.7168	Intermediate Similarity	NPD5967	Approved
0.7158	Intermediate Similarity	NPD6851	Approved
0.7158	Intermediate Similarity	NPD6853	Approved
0.7134	Intermediate Similarity	NPD7720	Phase 2
0.7127	Intermediate Similarity	NPD5445	Approved
0.7126	Intermediate Similarity	NPD7554	Discontinued
0.7117	Intermediate Similarity	NPD5301	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6681	Discovery
0.7086	Intermediate Similarity	NPD8031	Discontinued
0.7081	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD8323	Discontinued
0.7066	Intermediate Similarity	NPD7602	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5263	Approved
0.7024	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD3073	Approved
0.6987	Remote Similarity	NPD2561	Approved
0.6987	Remote Similarity	NPD3071	Approved
0.6987	Remote Similarity	NPD2562	Approved
0.6987	Remote Similarity	NPD3072	Approved
0.6982	Remote Similarity	NPD6088	Approved
0.6978	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6623	Phase 3
0.697	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1330	Phase 2
0.6957	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6295	Approved
0.6951	Remote Similarity	NPD6294	Approved
0.6946	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3908	Approved
0.6923	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4761	Approved
0.6923	Remote Similarity	NPD4762	Approved
0.6909	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD255	Approved
0.6908	Remote Similarity	NPD256	Approved
0.6905	Remote Similarity	NPD3400	Discontinued
0.6905	Remote Similarity	NPD1968	Approved
0.6905	Remote Similarity	NPD1967	Approved
0.6894	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6073	Approved
0.6886	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3040	Approved
0.6875	Remote Similarity	NPD9569	Approved
0.6864	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD8025	Phase 2
0.6857	Remote Similarity	NPD5355	Approved
0.6857	Remote Similarity	NPD5356	Approved
0.6848	Remote Similarity	NPD3552	Approved
0.6848	Remote Similarity	NPD3555	Approved
0.6848	Remote Similarity	NPD3554	Approved
0.6848	Remote Similarity	NPD3553	Approved
0.6845	Remote Similarity	NPD6967	Phase 2
0.6832	Remote Similarity	NPD4676	Approved
0.6829	Remote Similarity	NPD8643	Discontinued
0.6821	Remote Similarity	NPD6255	Approved
0.6821	Remote Similarity	NPD6256	Approved
0.6821	Remote Similarity	NPD6254	Approved
0.6814	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.681	Remote Similarity	NPD259	Phase 1
0.681	Remote Similarity	NPD5745	Approved
0.6804	Remote Similarity	NPD7810	Phase 3
0.6804	Remote Similarity	NPD7811	Phase 3
0.6802	Remote Similarity	NPD7613	Discontinued
0.68	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3125	Approved
0.6772	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.677	Remote Similarity	NPD4177	Approved
0.677	Remote Similarity	NPD4175	Approved
0.6769	Remote Similarity	NPD6253	Approved
0.6768	Remote Similarity	NPD5323	Approved
0.675	Remote Similarity	NPD3053	Approved
0.675	Remote Similarity	NPD3055	Approved
0.6747	Remote Similarity	NPD6852	Discontinued
0.674	Remote Similarity	NPD6747	Phase 1
0.673	Remote Similarity	NPD4659	Approved
0.6728	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD555	Phase 2
0.672	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD8292	Phase 2
0.6708	Remote Similarity	NPD4151	Approved
0.6708	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6677	Suspended
0.6704	Remote Similarity	NPD8070	Approved
0.6703	Remote Similarity	NPD5484	Approved
0.6703	Remote Similarity	NPD5485	Approved
0.6702	Remote Similarity	NPD7283	Approved
0.67	Remote Similarity	NPD6188	Approved
0.67	Remote Similarity	NPD6189	Approved
0.6687	Remote Similarity	NPD2568	Approved
0.6687	Remote Similarity	NPD5367	Discontinued
0.6687	Remote Similarity	NPD5310	Approved
0.6687	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5311	Approved
0.6687	Remote Similarity	NPD9537	Phase 1
0.6687	Remote Similarity	NPD9536	Phase 1
0.6687	Remote Similarity	NPD5746	Approved
0.6687	Remote Similarity	NPD5725	Approved
0.6686	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5613	Approved
0.6686	Remote Similarity	NPD5614	Approved
0.6684	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1759	Phase 1
0.6667	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7828	Discontinued
0.6667	Remote Similarity	NPD1519	Approved
0.6667	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1537	Approved
0.6667	Remote Similarity	NPD4153	Approved
0.6667	Remote Similarity	NPD1538	Phase 1
0.665	Remote Similarity	NPD6187	Approved
0.6647	Remote Similarity	NPD2209	Approved
0.6647	Remote Similarity	NPD6419	Discontinued
0.6647	Remote Similarity	NPD3536	Discontinued
0.6647	Remote Similarity	NPD2211	Approved
0.6647	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5299	Approved
0.6632	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4443	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD8315	Phase 1
0.6627	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD2614	Approved
0.6624	Remote Similarity	NPD4093	Discontinued
0.6615	Remote Similarity	NPD7282	Approved
0.6615	Remote Similarity	NPD6505	Approved
0.6615	Remote Similarity	NPD6504	Approved
0.6614	Remote Similarity	NPD6557	Phase 2
0.6609	Remote Similarity	NPD6390	Discontinued
0.6608	Remote Similarity	NPD5481	Discontinued
0.6606	Remote Similarity	NPD6407	Approved
0.6606	Remote Similarity	NPD6405	Approved
0.6605	Remote Similarity	NPD257	Approved
0.6605	Remote Similarity	NPD258	Approved
0.6603	Remote Similarity	NPD317	Approved
0.6603	Remote Similarity	NPD16	Approved
0.6603	Remote Similarity	NPD318	Approved
0.6603	Remote Similarity	NPD856	Approved
0.6603	Remote Similarity	NPD1758	Phase 1
0.6598	Remote Similarity	NPD7669	Phase 3
0.6592	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD3455	Phase 2
0.659	Remote Similarity	NPD2014	Approved
0.659	Remote Similarity	NPD2013	Approved
0.659	Remote Similarity	NPD2016	Approved
0.659	Remote Similarity	NPD3987	Approved
0.659	Remote Similarity	NPD3988	Approved
0.6587	Remote Similarity	NPD5314	Approved
0.6587	Remote Similarity	NPD8173	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