NPASS Compound

Structure

NPC473371 OpenBabel07101718222D 83 86 0 0 1 0 0 0 0 0999 V2000 1.0330 4.2540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7972 5.7641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1692 4.3347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8616 4.3347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7582 -2.1805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4549 -3.3606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5541 1.4033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7960 -1.9395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9321 1.1641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0064 -2.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2466 1.4033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0928 0.9147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4003 0.9147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9390 2.3805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7852 0.9147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5789 -5.7194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7852 2.8690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6315 1.4033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5907 1.7338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8600 -6.3812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4662 0.8850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7229 4.3472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4326 -4.4742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8030 -3.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9390 -1.5281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8510 4.7884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0154 3.8462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1890 -2.4203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7079 0.9147 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6352 -0.9757 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0269 0.9768 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9390 1.4033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3652 -4.7659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6315 2.3805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7137 -5.1360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4003 -0.0624 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3320 2.1657 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7767 3.3715 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5893 -2.4888 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9274 -6.0895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0928 -2.0167 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0522 0.2584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0154 2.8690 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8704 -1.7199 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3695 1.8919 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7201 -0.6331 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8616 1.4033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5541 -0.5510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7479 3.2641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6137 -2.5426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2466 -1.5281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1692 2.3805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9907 2.6462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7732 1.2938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2315 -1.4793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2917 -0.9326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2189 -4.8443 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -4.7079 -0.0624 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.2466 -0.5510 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.6316 2.8470 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8232 3.1579 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8616 2.3805 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6734 -2.2767 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3229 2.8690 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4946 -2.1211 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.9074 0.3259 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.7852 -2.0167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3895 -0.3545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.4777 2.8690 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2085 -6.7513 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0928 -2.9938 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6988 -0.6526 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0154 0.9147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5541 -1.5281 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0138 4.2043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5062 -3.5138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4003 -2.0167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1692 1.4033 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3490 3.3830 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7058 1.5855 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9858 -2.1005 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5802 -1.3738 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 26 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 10 65 1 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 32 1 0 0 0 0 14 17 1 0 0 0 0 14 32 2 0 0 0 0 15 18 2 0 0 0 0 15 32 1 0 0 0 0 16 20 2 0 0 0 0 16 33 1 0 0 0 0 17 34 2 0 0 0 0 18 34 1 0 0 0 0 19 21 1 0 0 0 0 20 40 1 0 0 0 0 21 42 1 0 0 0 0 22 26 1 0 0 0 0 23 33 2 0 0 0 0 23 35 1 0 0 0 0 24 33 1 0 0 0 0 25 41 1 0 0 0 0 25 67 1 0 0 0 0 29 7 1 6 0 0 0 29 47 1 0 0 0 0 29 58 1 0 0 0 0 30 8 1 6 0 0 0 30 68 1 0 0 0 0 31 9 1 6 0 0 0 31 45 1 0 0 0 0 31 83 1 0 0 0 0 34 69 1 0 0 0 0 35 40 2 0 0 0 0 35 57 1 0 0 0 0 36 13 1 1 0 0 0 36 48 1 0 0 0 0 36 59 1 0 0 0 0 37 19 1 1 0 0 0 37 54 1 0 0 0 0 37 60 1 0 0 0 0 38 22 1 1 0 0 0 38 49 1 0 0 0 0 38 61 1 0 0 0 0 39 24 1 1 0 0 0 39 50 1 0 0 0 0 39 65 1 0 0 0 0 40 70 1 0 0 0 0 41 51 1 0 0 0 0 41 71 1 6 0 0 0 42 66 1 0 0 0 0 42 72 1 6 0 0 0 43 27 1 1 0 0 0 43 52 1 0 0 0 0 43 62 1 0 0 0 0 44 28 1 1 0 0 0 44 56 1 0 0 0 0 44 63 1 0 0 0 0 45 53 1 0 0 0 0 45 64 1 6 0 0 0 46 30 1 1 0 0 0 46 55 1 0 0 0 0 46 66 1 0 0 0 0 47 62 2 3 0 0 0 47 73 1 0 0 0 0 48 58 2 3 0 0 0 48 74 1 0 0 0 0 49 60 2 3 0 0 0 49 75 1 0 0 0 0 50 63 2 3 0 0 0 50 76 1 0 0 0 0 51 59 2 3 0 0 0 51 77 1 0 0 0 0 52 64 2 3 0 0 0 52 78 1 0 0 0 0 53 61 2 3 0 0 0 53 79 1 0 0 0 0 54 66 1 0 0 0 0 54 80 2 0 0 0 0 55 65 1 0 0 0 0 55 81 2 0 0 0 0 56 82 2 0 0 0 0 56 83 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1187.55
Volume:	1164.338
LogP:	1.727
LogD:	0.664
LogS:	-1.248
# Rotatable Bonds:	21
TPSA:	405.96
# H-Bond Aceptor:	26
# H-Bond Donor:	13
# Rings:	4
# Heavy Atoms:	27

MedChem Properties

QED Drug-Likeness Score:	0.051
Synthetic Accessibility Score:	7.963
Fsp3:	0.607
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.4
MDCK Permeability:	5.938977483310737e-05
Pgp-inhibitor:	0.174
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.926
20% Bioavailability (F20%):	0.608
30% Bioavailability (F30%):	0.869

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.261
Plasma Protein Binding (PPB):	48.8615608215332%
Volume Distribution (VD):	0.44
Pgp-substrate:	34.032623291015625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.032
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.74
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.109
CYP3A4-substrate:	0.011

ADMET: Excretion

Clearance (CL):	1.323
Half-life (T1/2):	0.878

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.992
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.575
Skin Sensitization:	0.04
Carcinogencity:	0.009
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.899

Download Data

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

Natural Product: NPC473371

Natural Product ID:	NPC473371
*Common Name:**	Largamide E
IUPAC Name:	(2S)-N-[(2R)-1-[[(2S)-1-[[(2S,5S,8S,11R,12S,15S,18S,21R)-5-[(3-chloro-4-hydroxyphenyl)methyl]-21-hydroxy-2-[(1R)-1-hydroxyethyl]-4,11-dimethyl-15-(2-methylpropyl)-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]-2-[[(2R)-2,3-dihydroxypropanoyl]amino]-5-(4-hydroxyphenyl)pentanamide
Synonyms:	Largamide E
Standard InCHIKey:	DDRDKAKGHUYAPS-HGGGZJIKSA-N
Standard InCHI:	InChI=1S/C56H82ClN9O17/c1-26(2)22-38-49(75)60-37-19-21-42(72)66(54(37)80)46(30(8)68)55(81)65(10)39(24-33-16-20-40(70)35(57)23-33)50(76)63-44(28(5)6)56(82)83-31(9)45(53(79)61-38)64-52(78)43(27(3)4)62-47(73)29(7)58-48(74)36(59-51(77)41(71)25-67)13-11-12-32-14-17-34(69)18-15-32/h14-18,20,23,26-31,36-39,41-46,67-72H,11-13,19,21-22,24-25H2,1-10H3,(H,58,74)(H,59,77)(H,60,75)(H,61,79)(H,62,73)(H,63,76)(H,64,78)/t29-,30-,31-,36+,37+,38+,39+,41-,42-,43+,44+,45+,46+/m1/s1
SMILES:	OC[C@H](C(=N[C@H](C(=N[C@@H](C(=N[C@H](C(=N[C@@H]1C(=N[C@@H](CC(C)C)C(=N[C@H]2CC[C@H](N(C2=O)[C@H](C(=O)N([C@H](C(=N[C@H](C(=O)O[C@@H]1C)C(C)C)O)Cc1ccc(c(c1)Cl)O)C)[C@H](O)C)O)O)O)O)C(C)C)O)C)O)CCCc1ccc(cc1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL403901
PubChem CID:	44448225
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
NPO31273	Oscillatoria sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16930043]
NPO31273	Oscillatoria sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17328572]
NPO31273	Oscillatoria sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20525864]
NPO31273	Oscillatoria sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21473610]
NPO31273	Oscillatoria sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21999614]

☑ 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	=	10000.0	nM	PMID[561843]

☑ 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 NPC473371 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	242
0.1-0.2	1241
0.2-0.3	5851
0.3-0.4	12055
0.4-0.5	17314
0.5-0.6	5268
0.6-0.7	512
0.7-0.8	167
0.8-0.85	37
0.85-0.9	9
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8919	High Similarity	NPC469443
0.875	High Similarity	NPC50016
0.8737	High Similarity	NPC220060
0.8636	High Similarity	NPC273755
0.8594	High Similarity	NPC469444
0.8588	High Similarity	NPC473354
0.8557	High Similarity	NPC469445
0.8547	High Similarity	NPC45037
0.8523	High Similarity	NPC40234
0.8514	High Similarity	NPC107938
0.8514	High Similarity	NPC294516
0.8495	Intermediate Similarity	NPC65714
0.8483	Intermediate Similarity	NPC476227
0.8475	Intermediate Similarity	NPC230611
0.8453	Intermediate Similarity	NPC476321
0.8446	Intermediate Similarity	NPC194699
0.8446	Intermediate Similarity	NPC219350
0.8427	Intermediate Similarity	NPC306804
0.8427	Intermediate Similarity	NPC137627
0.8407	Intermediate Similarity	NPC471526
0.838	Intermediate Similarity	NPC473402
0.838	Intermediate Similarity	NPC26108
0.838	Intermediate Similarity	NPC279871
0.8361	Intermediate Similarity	NPC294951
0.836	Intermediate Similarity	NPC471592
0.8315	Intermediate Similarity	NPC475123
0.8315	Intermediate Similarity	NPC475204
0.8283	Intermediate Similarity	NPC25539
0.8278	Intermediate Similarity	NPC155506
0.8278	Intermediate Similarity	NPC159767
0.8274	Intermediate Similarity	NPC277306
0.8274	Intermediate Similarity	NPC469442
0.8261	Intermediate Similarity	NPC471050
0.8261	Intermediate Similarity	NPC471049
0.8261	Intermediate Similarity	NPC471048
0.8242	Intermediate Similarity	NPC194671
0.8242	Intermediate Similarity	NPC269750
0.8235	Intermediate Similarity	NPC473305
0.8235	Intermediate Similarity	NPC163961
0.8212	Intermediate Similarity	NPC46009
0.8177	Intermediate Similarity	NPC471165
0.8122	Intermediate Similarity	NPC248670
0.8095	Intermediate Similarity	NPC473378
0.8095	Intermediate Similarity	NPC473407
0.8031	Intermediate Similarity	NPC323662
0.801	Intermediate Similarity	NPC302715
0.7989	Intermediate Similarity	NPC102959
0.7947	Intermediate Similarity	NPC60516
0.7947	Intermediate Similarity	NPC61332
0.7947	Intermediate Similarity	NPC240130
0.7917	Intermediate Similarity	NPC328763
0.7861	Intermediate Similarity	NPC473404
0.7857	Intermediate Similarity	NPC477551
0.7853	Intermediate Similarity	NPC51047
0.7846	Intermediate Similarity	NPC477552
0.7846	Intermediate Similarity	NPC477550
0.7802	Intermediate Similarity	NPC209463
0.7784	Intermediate Similarity	NPC158277
0.7772	Intermediate Similarity	NPC89831
0.7692	Intermediate Similarity	NPC63931
0.7688	Intermediate Similarity	NPC227778
0.7676	Intermediate Similarity	NPC328494
0.767	Intermediate Similarity	NPC473491
0.7629	Intermediate Similarity	NPC470728
0.7622	Intermediate Similarity	NPC473693
0.7622	Intermediate Similarity	NPC471568
0.7569	Intermediate Similarity	NPC244336
0.7554	Intermediate Similarity	NPC61004
0.7527	Intermediate Similarity	NPC196091
0.7514	Intermediate Similarity	NPC302597
0.7488	Intermediate Similarity	NPC326027
0.7486	Intermediate Similarity	NPC262166
0.7476	Intermediate Similarity	NPC326333
0.7457	Intermediate Similarity	NPC239762
0.7457	Intermediate Similarity	NPC163392
0.7446	Intermediate Similarity	NPC471051
0.7446	Intermediate Similarity	NPC471052
0.7446	Intermediate Similarity	NPC471053
0.7444	Intermediate Similarity	NPC39431
0.7443	Intermediate Similarity	NPC81026
0.7435	Intermediate Similarity	NPC134413
0.7435	Intermediate Similarity	NPC45112
0.7435	Intermediate Similarity	NPC263507
0.7435	Intermediate Similarity	NPC271958
0.7433	Intermediate Similarity	NPC151030
0.7433	Intermediate Similarity	NPC269383
0.7432	Intermediate Similarity	NPC471527
0.7407	Intermediate Similarity	NPC136797
0.7403	Intermediate Similarity	NPC476268
0.7403	Intermediate Similarity	NPC244509
0.7389	Intermediate Similarity	NPC473341
0.7386	Intermediate Similarity	NPC266741
0.7385	Intermediate Similarity	NPC94862
0.738	Intermediate Similarity	NPC186617
0.7371	Intermediate Similarity	NPC315542
0.736	Intermediate Similarity	NPC248822
0.7333	Intermediate Similarity	NPC233702
0.7312	Intermediate Similarity	NPC472923
0.7306	Intermediate Similarity	NPC477637
0.7303	Intermediate Similarity	NPC16188
0.7293	Intermediate Similarity	NPC202198
0.7293	Intermediate Similarity	NPC122590
0.7292	Intermediate Similarity	NPC475421
0.7273	Intermediate Similarity	NPC91953
0.7268	Intermediate Similarity	NPC86678
0.7263	Intermediate Similarity	NPC49315
0.7249	Intermediate Similarity	NPC274198
0.7249	Intermediate Similarity	NPC198254
0.7245	Intermediate Similarity	NPC276120
0.7241	Intermediate Similarity	NPC127741
0.7241	Intermediate Similarity	NPC6570
0.7222	Intermediate Similarity	NPC174122
0.7222	Intermediate Similarity	NPC64140
0.7216	Intermediate Similarity	NPC197921
0.7216	Intermediate Similarity	NPC476989
0.7198	Intermediate Similarity	NPC5194
0.7198	Intermediate Similarity	NPC56685
0.7198	Intermediate Similarity	NPC261934
0.7189	Intermediate Similarity	NPC62104
0.7189	Intermediate Similarity	NPC1390
0.7188	Intermediate Similarity	NPC196243
0.7184	Intermediate Similarity	NPC81845
0.7181	Intermediate Similarity	NPC254700
0.7179	Intermediate Similarity	NPC470112
0.7179	Intermediate Similarity	NPC167763
0.7179	Intermediate Similarity	NPC470903
0.7172	Intermediate Similarity	NPC234069
0.7164	Intermediate Similarity	NPC477632
0.7164	Intermediate Similarity	NPC477638
0.7158	Intermediate Similarity	NPC276506
0.7151	Intermediate Similarity	NPC469243
0.7143	Intermediate Similarity	NPC141957
0.7143	Intermediate Similarity	NPC328649
0.7135	Intermediate Similarity	NPC477462
0.7135	Intermediate Similarity	NPC297145
0.7135	Intermediate Similarity	NPC197743
0.7128	Intermediate Similarity	NPC223207
0.7127	Intermediate Similarity	NPC2501
0.7119	Intermediate Similarity	NPC469426
0.7119	Intermediate Similarity	NPC469427
0.7114	Intermediate Similarity	NPC314083
0.7113	Intermediate Similarity	NPC97526
0.7113	Intermediate Similarity	NPC119652
0.7112	Intermediate Similarity	NPC241794
0.7107	Intermediate Similarity	NPC299806
0.7105	Intermediate Similarity	NPC280022
0.7095	Intermediate Similarity	NPC295795
0.709	Intermediate Similarity	NPC290755
0.709	Intermediate Similarity	NPC304074
0.709	Intermediate Similarity	NPC471771
0.7079	Intermediate Similarity	NPC176226
0.7079	Intermediate Similarity	NPC469360
0.7073	Intermediate Similarity	NPC473450
0.7062	Intermediate Similarity	NPC476259
0.7059	Intermediate Similarity	NPC475544
0.7056	Intermediate Similarity	NPC314358
0.7053	Intermediate Similarity	NPC473502
0.7053	Intermediate Similarity	NPC63040
0.7049	Intermediate Similarity	NPC162104
0.7037	Intermediate Similarity	NPC210377
0.7037	Intermediate Similarity	NPC5719
0.7037	Intermediate Similarity	NPC22883
0.7037	Intermediate Similarity	NPC217804
0.7024	Intermediate Similarity	NPC123859
0.702	Intermediate Similarity	NPC138083
0.7017	Intermediate Similarity	NPC135121
0.7	Intermediate Similarity	NPC316008
0.7	Intermediate Similarity	NPC313867
0.7	Intermediate Similarity	NPC15068
0.699	Remote Similarity	NPC32064
0.6976	Remote Similarity	NPC50548
0.6952	Remote Similarity	NPC56635
0.6944	Remote Similarity	NPC314388
0.6944	Remote Similarity	NPC315283
0.6935	Remote Similarity	NPC473580
0.6931	Remote Similarity	NPC477526
0.6927	Remote Similarity	NPC144314
0.6919	Remote Similarity	NPC478005
0.6915	Remote Similarity	NPC319320
0.6915	Remote Similarity	NPC287757
0.6914	Remote Similarity	NPC257390
0.6908	Remote Similarity	NPC242728
0.6907	Remote Similarity	NPC475532
0.6906	Remote Similarity	NPC477217
0.6906	Remote Similarity	NPC201244
0.6904	Remote Similarity	NPC153554
0.6897	Remote Similarity	NPC477631
0.6889	Remote Similarity	NPC161069
0.6881	Remote Similarity	NPC477636
0.6879	Remote Similarity	NPC319766
0.6878	Remote Similarity	NPC329295
0.6878	Remote Similarity	NPC149962
0.6872	Remote Similarity	NPC17698
0.6872	Remote Similarity	NPC268841
0.6872	Remote Similarity	NPC164608
0.6872	Remote Similarity	NPC165285
0.6872	Remote Similarity	NPC46098
0.6872	Remote Similarity	NPC307357
0.6868	Remote Similarity	NPC262077
0.6866	Remote Similarity	NPC4910

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 NPC473371 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	496
0.2-0.3	968
0.3-0.4	2142
0.4-0.5	3347
0.5-0.6	1891
0.6-0.7	161
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
0.7435	Intermediate Similarity	NPD7959	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD8014	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD6312	Discontinued
0.7079	Intermediate Similarity	NPD7978	Discontinued
0.7068	Intermediate Similarity	NPD7608	Discontinued
0.7024	Intermediate Similarity	NPD7810	Phase 3
0.7024	Intermediate Similarity	NPD7811	Phase 3
0.7	Intermediate Similarity	NPD8303	Discontinued
0.6957	Remote Similarity	NPD4731	Phase 3
0.6834	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7131	Phase 3
0.6825	Remote Similarity	NPD8019	Approved
0.6793	Remote Similarity	NPD5308	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD4588	Clinical (unspecified phase)
0.676	Remote Similarity	NPD8173	Phase 2
0.676	Remote Similarity	NPD8172	Phase 2
0.6753	Remote Similarity	NPD7484	Phase 3
0.6753	Remote Similarity	NPD7485	Phase 3
0.6739	Remote Similarity	NPD5309	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD8323	Discontinued
0.6702	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3136	Phase 2
0.6649	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7495	Discontinued
0.6648	Remote Similarity	NPD6346	Approved
0.6632	Remote Similarity	NPD8417	Discontinued
0.6622	Remote Similarity	NPD7805	Phase 3
0.6601	Remote Similarity	NPD6853	Approved
0.6601	Remote Similarity	NPD6851	Approved
0.6599	Remote Similarity	NPD5137	Approved
0.6598	Remote Similarity	NPD8031	Discontinued
0.6596	Remote Similarity	NPD6689	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4971	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4659	Approved
0.6508	Remote Similarity	NPD7303	Discontinued
0.6505	Remote Similarity	NPD3400	Discontinued
0.6505	Remote Similarity	NPD6676	Phase 2
0.6502	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7523	Phase 3
0.6468	Remote Similarity	NPD3933	Discontinued
0.6468	Remote Similarity	NPD5096	Phase 3
0.6468	Remote Similarity	NPD5095	Phase 3
0.6467	Remote Similarity	NPD7450	Phase 2
0.6464	Remote Similarity	NPD8265	Approved
0.6452	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD4103	Phase 2
0.6441	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7574	Phase 2
0.6432	Remote Similarity	NPD4914	Approved
0.6429	Remote Similarity	NPD4363	Phase 3
0.6429	Remote Similarity	NPD4360	Phase 2
0.6425	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD3364	Phase 3
0.6411	Remote Similarity	NPD3819	Phase 2
0.641	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6297	Approved
0.6398	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD6681	Discovery
0.6398	Remote Similarity	NPD4361	Phase 2
0.6385	Remote Similarity	NPD5544	Approved
0.6384	Remote Similarity	NPD3125	Approved
0.6382	Remote Similarity	NPD4652	Approved
0.6372	Remote Similarity	NPD4386	Approved
0.6372	Remote Similarity	NPD4387	Approved
0.6359	Remote Similarity	NPD7972	Discontinued
0.6359	Remote Similarity	NPD6905	Phase 2
0.6359	Remote Similarity	NPD4485	Approved
0.6345	Remote Similarity	NPD2098	Approved
0.634	Remote Similarity	NPD4424	Discontinued
0.6335	Remote Similarity	NPD7613	Discontinued
0.6332	Remote Similarity	NPD5649	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD5745	Approved
0.631	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD7565	Approved
0.6305	Remote Similarity	NPD5312	Approved
0.6305	Remote Similarity	NPD5313	Approved
0.63	Remote Similarity	NPD8356	Approved
0.6298	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6058	Phase 2
0.6281	Remote Similarity	NPD3365	Discontinued
0.6275	Remote Similarity	NPD5484	Approved
0.6275	Remote Similarity	NPD5485	Approved
0.6269	Remote Similarity	NPD8315	Phase 1
0.6264	Remote Similarity	NPD2078	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD4064	Discontinued
0.6263	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD8430	Approved
0.6255	Remote Similarity	NPD8463	Approved
0.625	Remote Similarity	NPD2888	Approved
0.625	Remote Similarity	NPD2889	Approved
0.625	Remote Similarity	NPD2890	Approved
0.625	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2017	Approved
0.6244	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD2097	Approved
0.6243	Remote Similarity	NPD4617	Approved
0.6243	Remote Similarity	NPD4620	Approved
0.6243	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD5203	Approved
0.6243	Remote Similarity	NPD5201	Approved
0.6237	Remote Similarity	NPD6056	Approved
0.6237	Remote Similarity	NPD6057	Approved
0.6232	Remote Similarity	NPD7281	Phase 3
0.6232	Remote Similarity	NPD8064	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD7280	Phase 3
0.6224	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD8162	Phase 2
0.6221	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.621	Remote Similarity	NPD8161	Suspended
0.6209	Remote Similarity	NPD5746	Approved
0.6203	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD3098	Discontinued
0.62	Remote Similarity	NPD2904	Discontinued
0.6198	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD5119	Approved
0.6196	Remote Similarity	NPD5120	Approved
0.6196	Remote Similarity	NPD5121	Approved
0.6195	Remote Similarity	NPD3885	Approved
0.619	Remote Similarity	NPD8025	Phase 2
0.6186	Remote Similarity	NPD4974	Approved
0.6186	Remote Similarity	NPD4975	Approved
0.6183	Remote Similarity	NPD7230	Approved
0.6183	Remote Similarity	NPD7231	Approved
0.6182	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD8070	Approved
0.6175	Remote Similarity	NPD1330	Phase 2
0.6175	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.617	Remote Similarity	NPD8076	Discontinued
0.6162	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5967	Approved
0.6158	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD1967	Approved
0.6158	Remote Similarity	NPD1968	Approved
0.6158	Remote Similarity	NPD2575	Approved
0.6154	Remote Similarity	NPD8027	Approved
0.615	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6505	Approved
0.6132	Remote Similarity	NPD6504	Approved
0.6131	Remote Similarity	NPD8351	Phase 2
0.6129	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD3974	Phase 2
0.6117	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD3879	Approved
0.6114	Remote Similarity	NPD3536	Discontinued
0.6111	Remote Similarity	NPD5772	Approved
0.6111	Remote Similarity	NPD5773	Approved
0.6105	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD1969	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD1973	Approved
0.6103	Remote Similarity	NPD1972	Approved
0.6103	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD5723	Approved
0.61	Remote Similarity	NPD5218	Approved
0.61	Remote Similarity	NPD5219	Approved
0.6096	Remote Similarity	NPD3552	Approved
0.6096	Remote Similarity	NPD3555	Approved
0.6096	Remote Similarity	NPD3553	Approved
0.6096	Remote Similarity	NPD6852	Discontinued
0.6096	Remote Similarity	NPD3554	Approved
0.6094	Remote Similarity	NPD6667	Approved
0.6094	Remote Similarity	NPD6666	Approved
0.6089	Remote Similarity	NPD2584	Suspended
0.6089	Remote Similarity	NPD6107	Approved
0.6087	Remote Similarity	NPD4619	Approved
0.6087	Remote Similarity	NPD4621	Approved
0.6085	Remote Similarity	NPD7617	Discontinued
0.6082	Remote Similarity	NPD6390	Discontinued
0.6077	Remote Similarity	NPD5035	Approved
0.6075	Remote Similarity	NPD7429	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD8643	Discontinued
0.6071	Remote Similarity	NPD3878	Approved
0.6068	Remote Similarity	NPD6020	Phase 2
0.6066	Remote Similarity	NPD5037	Approved
0.6066	Remote Similarity	NPD4698	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD5038	Approved
0.6065	Remote Similarity	NPD5652	Approved
0.6065	Remote Similarity	NPD4915	Approved
0.6065	Remote Similarity	NPD5650	Approved
0.6065	Remote Similarity	NPD5651	Approved
0.6064	Remote Similarity	NPD1753	Discontinued
0.6058	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD8164	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD829	Discontinued
0.6052	Remote Similarity	NPD4086	Phase 1
0.6048	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD7451	Discontinued
0.6043	Remote Similarity	NPD6073	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