NPASS Compound

Structure

NPC81026 OpenBabel07101719512D 39 40 0 0 1 0 0 0 0 0999 V2000 2.3169 0.2282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1618 -1.2352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6881 -1.9825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3936 0.2596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2385 -4.5321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9608 1.1450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4720 -5.5390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8516 -4.0443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6965 -3.5565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3936 -1.2352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7273 -3.1275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9216 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0067 -2.5809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3169 -4.5321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9608 -5.4489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3169 -0.7474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7273 -2.1519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7665 -0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3936 -4.0443 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9608 0.1694 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0067 -3.5565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8516 -2.0931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4720 -4.0443 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6965 -2.5809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.2795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4720 -1.2352 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7665 -4.7917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8057 -3.1275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8516 -1.1175 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0 -1.9216 -5.2795 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8057 -2.1519 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -4.7917 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.5414 -2.0931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3337 -6.1963 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3936 -5.5390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7665 -3.2970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4720 0.2596 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 7 33 1 0 0 0 0 8 9 2 0 0 0 0 8 21 1 0 0 0 0 9 24 1 0 0 0 0 10 17 2 0 0 0 0 10 18 1 0 0 0 0 11 17 1 0 0 0 0 11 19 1 0 0 0 0 12 18 1 0 0 0 0 12 20 1 0 0 0 0 13 21 2 0 0 0 0 13 22 1 0 0 0 0 14 21 1 0 0 0 0 15 25 1 0 0 0 0 15 31 1 0 0 0 0 18 4 1 6 0 0 0 19 5 1 1 0 0 0 19 27 1 0 0 0 0 20 6 1 6 0 0 0 20 39 1 0 0 0 0 22 24 2 0 0 0 0 22 30 1 0 0 0 0 23 14 1 6 0 0 0 23 28 1 0 0 0 0 23 33 1 0 0 0 0 24 34 1 0 0 0 0 25 33 1 0 0 0 0 25 35 2 0 0 0 0 26 16 1 6 0 0 0 26 29 1 0 0 0 0 26 32 1 0 0 0 0 27 31 2 3 0 0 0 27 36 1 0 0 0 0 28 32 2 3 0 0 0 28 37 1 0 0 0 0 29 38 2 0 0 0 0 29 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	655.21
Volume:	582.944
LogP:	4.44
LogD:	3.914
LogS:	-3.938
# Rotatable Bonds:	3
TPSA:	125.04
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.26
Synthetic Accessibility Score:	5.003
Fsp3:	0.586
Lipinski Rule-of-5:	Accepted
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:	-4.645
MDCK Permeability:	1.2049111319356598e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.189
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.88

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.754
Plasma Protein Binding (PPB):	92.55693817138672%
Volume Distribution (VD):	0.441
Pgp-substrate:	10.195751190185547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.055
CYP2C19-inhibitor:	0.295
CYP2C19-substrate:	0.604
CYP2C9-inhibitor:	0.335
CYP2C9-substrate:	0.384
CYP2D6-inhibitor:	0.06
CYP2D6-substrate:	0.222
CYP3A4-inhibitor:	0.926
CYP3A4-substrate:	0.487

ADMET: Excretion

Clearance (CL):	8.056
Half-life (T1/2):	0.262

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.917
Drug-inuced Liver Injury (DILI):	0.442
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.244
Maximum Recommended Daily Dose:	0.724
Skin Sensitization:	0.055
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.024

Download Data

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

Natural Product: NPC81026

Natural Product ID:	NPC81026
*Common Name:**	Neosiphoniamolide A
IUPAC Name:	(3S,6S,12S,14E,16R,18S)-6-[(4-hydroxy-3-iodophenyl)methyl]-7,12,14,16,18-pentamethyl-3-propan-2-yl-1-oxa-4,7,10-triazacyclooctadec-14-ene-2,5,8,11-tetrone
Synonyms:
Standard InCHIKey:	HADLOGUIGHOPEZ-ZCRKUDLBSA-N
Standard InCHI:	InChI=1S/C29H42IN3O6/c1-16(2)26-29(38)39-20(6)12-18(4)10-17(3)11-19(5)27(36)31-15-25(35)33(7)23(28(37)32-26)14-21-8-9-24(34)22(30)13-21/h8-10,13,16,18-20,23,26,34H,11-12,14-15H2,1-7H3,(H,31,36)(H,32,37)/b17-10+/t18-,19-,20-,23-,26-/m0/s1
SMILES:	C[C@H]1C[C@@H](C)/C=C(C)/C[C@H](C)C(=NCC(=O)N([C@H](C(=N[C@H](C(=O)O1)C(C)C)O)Cc1ccc(c(c1)I)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516919
PubChem CID:	10484440
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
NPO19323	Neosiphonia superstes	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760068]
NPO19323	Neosiphonia superstes	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7853010]
NPO19323	Neosiphonia superstes	Species	Rhodomelaceae	Eukaryota	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
Others	13

Activity Type	# Activity
Organism	13

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6602	Organism	Ustilago nuda	Ustilago nuda	IC90	>	5.0	ppm	PMID[541425]
NPT1815	Organism	Helminthosporium	Helminthosporium	IC90	=	5.0	ppm	PMID[541425]
NPT828	Organism	Phaeosphaeria nodorum	Phaeosphaeria nodorum	IC90	>	5.0	ppm	PMID[541425]
NPT6303	Organism	Oculimacula yallundae	Oculimacula yallundae	IC90	>	5.0	ppm	PMID[541425]
NPT529	Organism	Rhizoctonia solani	Rhizoctonia solani	IC90	>	5.0	ppm	PMID[541425]
NPT962	Organism	Alternaria alternata	Alternaria alternata	IC90	>	5.0	ppm	PMID[541425]
NPT2707	Organism	Fusarium	Fusarium	IC90	>	5.0	ppm	PMID[541425]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC90	=	5.0	ppm	PMID[541425]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	IC90	>	5.0	ppm	PMID[541425]
NPT6605	Organism	Pythium vexans	Pythium vexans	IC90	>	5.0	ppm	PMID[541425]
NPT6606	Organism	Pythium rostratum	Pythium rostratum	IC90	>	5.0	ppm	PMID[541425]
NPT5694	Organism	Phytophthora cinnamomi	Phytophthora cinnamomi	IC90	>	5.0	ppm	PMID[541425]
NPT2793	Organism	Phytophthora citrophthora	Phytophthora citrophthora	IC90	>	5.0	ppm	PMID[541425]

☑ 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 NPC81026 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	145
0.1-0.2	853
0.2-0.3	4771
0.3-0.4	12499
0.4-0.5	13285
0.5-0.6	9525
0.6-0.7	1130
0.7-0.8	421
0.8-0.85	59
0.85-0.9	6
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9925	High Similarity	NPC266741
0.9504	High Similarity	NPC39431
0.8511	High Similarity	NPC6570
0.8506	High Similarity	NPC294516
0.8506	High Similarity	NPC107938
0.8397	Intermediate Similarity	NPC40234
0.8397	Intermediate Similarity	NPC475204
0.8397	Intermediate Similarity	NPC475123
0.8397	Intermediate Similarity	NPC46009
0.8377	Intermediate Similarity	NPC472923
0.8344	Intermediate Similarity	NPC230611
0.8333	Intermediate Similarity	NPC197921
0.8333	Intermediate Similarity	NPC476989
0.8299	Intermediate Similarity	NPC16188
0.8291	Intermediate Similarity	NPC248670
0.8291	Intermediate Similarity	NPC306804
0.8291	Intermediate Similarity	NPC273755
0.8291	Intermediate Similarity	NPC137627
0.8276	Intermediate Similarity	NPC469360
0.8276	Intermediate Similarity	NPC91953
0.8273	Intermediate Similarity	NPC296712
0.8269	Intermediate Similarity	NPC473502
0.8267	Intermediate Similarity	NPC262166
0.8255	Intermediate Similarity	NPC473491
0.8239	Intermediate Similarity	NPC476227
0.8239	Intermediate Similarity	NPC471165
0.8239	Intermediate Similarity	NPC279871
0.8239	Intermediate Similarity	NPC155506
0.8239	Intermediate Similarity	NPC473354
0.8239	Intermediate Similarity	NPC158277
0.8239	Intermediate Similarity	NPC159767
0.8239	Intermediate Similarity	NPC26108
0.8239	Intermediate Similarity	NPC473402
0.8235	Intermediate Similarity	NPC474862
0.8228	Intermediate Similarity	NPC89831
0.8187	Intermediate Similarity	NPC50016
0.8165	Intermediate Similarity	NPC196091
0.8158	Intermediate Similarity	NPC476268
0.8158	Intermediate Similarity	NPC473580
0.8141	Intermediate Similarity	NPC63931
0.8101	Intermediate Similarity	NPC186617
0.8099	Intermediate Similarity	NPC246079
0.8086	Intermediate Similarity	NPC194671
0.8086	Intermediate Similarity	NPC45037
0.8086	Intermediate Similarity	NPC269750
0.8079	Intermediate Similarity	NPC233702
0.8069	Intermediate Similarity	NPC313694
0.8069	Intermediate Similarity	NPC242159
0.8065	Intermediate Similarity	NPC469243
0.805	Intermediate Similarity	NPC471568
0.805	Intermediate Similarity	NPC473693
0.8039	Intermediate Similarity	NPC244509
0.8038	Intermediate Similarity	NPC209463
0.8026	Intermediate Similarity	NPC261934
0.8026	Intermediate Similarity	NPC202198
0.8026	Intermediate Similarity	NPC56685
0.8026	Intermediate Similarity	NPC5194
0.8013	Intermediate Similarity	NPC324081
0.7988	Intermediate Similarity	NPC476321
0.7988	Intermediate Similarity	NPC473404
0.7975	Intermediate Similarity	NPC254700
0.7972	Intermediate Similarity	NPC326966
0.7949	Intermediate Similarity	NPC475544
0.7939	Intermediate Similarity	NPC471526
0.7911	Intermediate Similarity	NPC223207
0.7892	Intermediate Similarity	NPC294951
0.7885	Intermediate Similarity	NPC244336
0.7883	Intermediate Similarity	NPC319950
0.7877	Intermediate Similarity	NPC127741
0.7866	Intermediate Similarity	NPC475421
0.7862	Intermediate Similarity	NPC471771
0.7862	Intermediate Similarity	NPC304074
0.7862	Intermediate Similarity	NPC290755
0.7862	Intermediate Similarity	NPC61004
0.7852	Intermediate Similarity	NPC317254
0.7847	Intermediate Similarity	NPC257390
0.7832	Intermediate Similarity	NPC478147
0.7812	Intermediate Similarity	NPC302597
0.7793	Intermediate Similarity	NPC244866
0.7784	Intermediate Similarity	NPC471048
0.7784	Intermediate Similarity	NPC471050
0.7784	Intermediate Similarity	NPC471049
0.7771	Intermediate Similarity	NPC287757
0.7771	Intermediate Similarity	NPC319320
0.777	Intermediate Similarity	NPC56634
0.7762	Intermediate Similarity	NPC469666
0.7755	Intermediate Similarity	NPC471265
0.7755	Intermediate Similarity	NPC471264
0.7755	Intermediate Similarity	NPC68865
0.7738	Intermediate Similarity	NPC315542
0.7725	Intermediate Similarity	NPC167763
0.7725	Intermediate Similarity	NPC470112
0.7725	Intermediate Similarity	NPC470903
0.7716	Intermediate Similarity	NPC274198
0.7716	Intermediate Similarity	NPC198254
0.7714	Intermediate Similarity	NPC142577
0.7714	Intermediate Similarity	NPC27581
0.7708	Intermediate Similarity	NPC325651
0.7707	Intermediate Similarity	NPC326349
0.7707	Intermediate Similarity	NPC323336
0.7706	Intermediate Similarity	NPC102959
0.7692	Intermediate Similarity	NPC476353
0.7673	Intermediate Similarity	NPC241794
0.7671	Intermediate Similarity	NPC470392
0.7661	Intermediate Similarity	NPC240130
0.7661	Intermediate Similarity	NPC163961
0.7661	Intermediate Similarity	NPC60516
0.7661	Intermediate Similarity	NPC61332
0.7661	Intermediate Similarity	NPC473305
0.7654	Intermediate Similarity	NPC280022
0.7651	Intermediate Similarity	NPC163392
0.7651	Intermediate Similarity	NPC239762
0.7647	Intermediate Similarity	NPC94862
0.7633	Intermediate Similarity	NPC299806
0.7626	Intermediate Similarity	NPC283760
0.7625	Intermediate Similarity	NPC133470
0.7625	Intermediate Similarity	NPC289776
0.7625	Intermediate Similarity	NPC191863
0.7616	Intermediate Similarity	NPC473378
0.7616	Intermediate Similarity	NPC473407
0.7607	Intermediate Similarity	NPC276506
0.7603	Intermediate Similarity	NPC45191
0.76	Intermediate Similarity	NPC469427
0.76	Intermediate Similarity	NPC263493
0.76	Intermediate Similarity	NPC469426
0.76	Intermediate Similarity	NPC269398
0.7597	Intermediate Similarity	NPC132771
0.7582	Intermediate Similarity	NPC135121
0.7576	Intermediate Similarity	NPC136797
0.7566	Intermediate Similarity	NPC201244
0.7566	Intermediate Similarity	NPC313867
0.7566	Intermediate Similarity	NPC477217
0.7566	Intermediate Similarity	NPC316008
0.7561	Intermediate Similarity	NPC328494
0.755	Intermediate Similarity	NPC189724
0.755	Intermediate Similarity	NPC83289
0.755	Intermediate Similarity	NPC139326
0.755	Intermediate Similarity	NPC212850
0.755	Intermediate Similarity	NPC161069
0.7548	Intermediate Similarity	NPC475168
0.7548	Intermediate Similarity	NPC7817
0.7544	Intermediate Similarity	NPC329731
0.7544	Intermediate Similarity	NPC4910
0.7536	Intermediate Similarity	NPC470544
0.7532	Intermediate Similarity	NPC9373
0.753	Intermediate Similarity	NPC196243
0.7529	Intermediate Similarity	NPC302715
0.7529	Intermediate Similarity	NPC65714
0.7529	Intermediate Similarity	NPC328763
0.7518	Intermediate Similarity	NPC118202
0.7516	Intermediate Similarity	NPC314358
0.7514	Intermediate Similarity	NPC477526
0.75	Intermediate Similarity	NPC314388
0.75	Intermediate Similarity	NPC315283
0.75	Intermediate Similarity	NPC476978
0.7485	Intermediate Similarity	NPC141957
0.7485	Intermediate Similarity	NPC328649
0.7484	Intermediate Similarity	NPC56635
0.7483	Intermediate Similarity	NPC168113
0.7482	Intermediate Similarity	NPC470545
0.7481	Intermediate Similarity	NPC474149
0.7468	Intermediate Similarity	NPC123011
0.7468	Intermediate Similarity	NPC329761
0.7468	Intermediate Similarity	NPC225648
0.7468	Intermediate Similarity	NPC145113
0.7468	Intermediate Similarity	NPC256689
0.7467	Intermediate Similarity	NPC98424
0.7467	Intermediate Similarity	NPC92784
0.7467	Intermediate Similarity	NPC470884
0.7467	Intermediate Similarity	NPC178662
0.7467	Intermediate Similarity	NPC476133
0.7465	Intermediate Similarity	NPC252878
0.7456	Intermediate Similarity	NPC477637
0.7452	Intermediate Similarity	NPC473341
0.7451	Intermediate Similarity	NPC209509
0.7451	Intermediate Similarity	NPC5620
0.7448	Intermediate Similarity	NPC319766
0.7447	Intermediate Similarity	NPC476183
0.7447	Intermediate Similarity	NPC190663
0.7443	Intermediate Similarity	NPC473371
0.7439	Intermediate Similarity	NPC129486
0.7439	Intermediate Similarity	NPC315388
0.7434	Intermediate Similarity	NPC197682
0.7434	Intermediate Similarity	NPC251439
0.7434	Intermediate Similarity	NPC176226
0.7432	Intermediate Similarity	NPC274732
0.7429	Intermediate Similarity	NPC470546
0.7417	Intermediate Similarity	NPC46098
0.7417	Intermediate Similarity	NPC268841
0.7417	Intermediate Similarity	NPC322526
0.7417	Intermediate Similarity	NPC307357
0.7417	Intermediate Similarity	NPC48202
0.7414	Intermediate Similarity	NPC248822
0.7413	Intermediate Similarity	NPC6975
0.7413	Intermediate Similarity	NPC46427
0.7407	Intermediate Similarity	NPC258056
0.7405	Intermediate Similarity	NPC470902
0.7401	Intermediate Similarity	NPC471592
0.7397	Intermediate Similarity	NPC17374
0.7394	Intermediate Similarity	NPC202521

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 NPC81026 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	101
0.1-0.2	396
0.2-0.3	848
0.3-0.4	1817
0.4-0.5	3057
0.5-0.6	2146
0.6-0.7	736
0.7-0.8	46
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8169	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD3136	Phase 2
0.8146	Intermediate Similarity	NPD7131	Phase 3
0.8052	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD8303	Discontinued
0.7793	Intermediate Similarity	NPD5745	Approved
0.7785	Intermediate Similarity	NPD7978	Discontinued
0.7727	Intermediate Similarity	NPD7303	Discontinued
0.7688	Intermediate Similarity	NPD2098	Approved
0.7655	Intermediate Similarity	NPD5746	Approved
0.7654	Intermediate Similarity	NPD7484	Phase 3
0.7654	Intermediate Similarity	NPD7485	Phase 3
0.7562	Intermediate Similarity	NPD2097	Approved
0.7534	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7608	Discontinued
0.75	Intermediate Similarity	NPD4652	Approved
0.75	Intermediate Similarity	NPD6390	Discontinued
0.75	Intermediate Similarity	NPD6346	Approved
0.7483	Intermediate Similarity	NPD7450	Phase 2
0.7439	Intermediate Similarity	NPD2017	Approved
0.7439	Intermediate Similarity	NPD2889	Approved
0.7439	Intermediate Similarity	NPD2890	Approved
0.7439	Intermediate Similarity	NPD2888	Approved
0.7438	Intermediate Similarity	NPD7495	Discontinued
0.7431	Intermediate Similarity	NPD3125	Approved
0.7413	Intermediate Similarity	NPD2584	Suspended
0.7386	Intermediate Similarity	NPD6681	Discovery
0.7361	Intermediate Similarity	NPD4659	Approved
0.7342	Intermediate Similarity	NPD7523	Phase 3
0.7338	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD8019	Approved
0.7285	Intermediate Similarity	NPD8172	Phase 2
0.7285	Intermediate Similarity	NPD8173	Phase 2
0.7241	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD2562	Approved
0.7172	Intermediate Similarity	NPD2561	Approved
0.7163	Intermediate Similarity	NPD9568	Approved
0.7163	Intermediate Similarity	NPD3123	Discovery
0.7161	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD8031	Discontinued
0.7152	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4103	Phase 2
0.7143	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1725	Approved
0.7134	Intermediate Similarity	NPD8323	Discontinued
0.7133	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1330	Phase 2
0.7115	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD317	Approved
0.7113	Intermediate Similarity	NPD318	Approved
0.7113	Intermediate Similarity	NPD16	Approved
0.7113	Intermediate Similarity	NPD856	Approved
0.7105	Intermediate Similarity	NPD555	Phase 2
0.7105	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7451	Discontinued
0.707	Intermediate Similarity	NPD3400	Discontinued
0.707	Intermediate Similarity	NPD5481	Discontinued
0.7063	Intermediate Similarity	NPD4186	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1759	Phase 1
0.7045	Intermediate Similarity	NPD6089	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD5291	Approved
0.7042	Intermediate Similarity	NPD5292	Approved
0.7034	Intermediate Similarity	NPD3421	Phase 3
0.7033	Intermediate Similarity	NPD7810	Phase 3
0.7033	Intermediate Similarity	NPD7811	Phase 3
0.7032	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3553	Approved
0.7013	Intermediate Similarity	NPD3554	Approved
0.7013	Intermediate Similarity	NPD3555	Approved
0.7013	Intermediate Similarity	NPD3552	Approved
0.7011	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3536	Discontinued
0.6993	Remote Similarity	NPD1758	Phase 1
0.6986	Remote Similarity	NPD5338	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD259	Phase 1
0.6972	Remote Similarity	NPD255	Approved
0.6972	Remote Similarity	NPD256	Approved
0.697	Remote Similarity	NPD5773	Approved
0.697	Remote Similarity	NPD7972	Discontinued
0.697	Remote Similarity	NPD5772	Approved
0.6966	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7613	Discontinued
0.6951	Remote Similarity	NPD2513	Approved
0.695	Remote Similarity	NPD2234	Approved
0.695	Remote Similarity	NPD2228	Approved
0.695	Remote Similarity	NPD2229	Approved
0.6948	Remote Similarity	NPD3054	Approved
0.6948	Remote Similarity	NPD3052	Approved
0.6943	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4175	Approved
0.6933	Remote Similarity	NPD4177	Approved
0.6932	Remote Similarity	NPD6853	Approved
0.6932	Remote Similarity	NPD6851	Approved
0.6928	Remote Similarity	NPD825	Approved
0.6928	Remote Similarity	NPD826	Approved
0.6923	Remote Similarity	NPD2239	Approved
0.6923	Remote Similarity	NPD2240	Approved
0.6918	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5356	Approved
0.6909	Remote Similarity	NPD3007	Approved
0.6909	Remote Similarity	NPD5355	Approved
0.6909	Remote Similarity	NPD2515	Approved
0.6908	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2891	Approved
0.6889	Remote Similarity	NPD855	Approved
0.6889	Remote Similarity	NPD854	Approved
0.6887	Remote Similarity	NPD4125	Approved
0.6882	Remote Similarity	NPD2517	Approved
0.6875	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6667	Approved
0.6875	Remote Similarity	NPD6666	Approved
0.6871	Remote Similarity	NPD4648	Approved
0.6871	Remote Similarity	NPD4647	Approved
0.6871	Remote Similarity	NPD4646	Approved
0.6867	Remote Similarity	NPD4557	Approved
0.6864	Remote Similarity	NPD7133	Discontinued
0.6863	Remote Similarity	NPD6405	Approved
0.6863	Remote Similarity	NPD6407	Approved
0.6863	Remote Similarity	NPD1423	Approved
0.6859	Remote Similarity	NPD3480	Approved
0.6859	Remote Similarity	NPD1753	Discontinued
0.6855	Remote Similarity	NPD1967	Approved
0.6855	Remote Similarity	NPD1968	Approved
0.6855	Remote Similarity	NPD6676	Phase 2
0.6852	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2047	Approved
0.6842	Remote Similarity	NPD2043	Approved
0.6842	Remote Similarity	NPD2044	Approved
0.6842	Remote Similarity	NPD2051	Approved
0.6842	Remote Similarity	NPD2046	Approved
0.6842	Remote Similarity	NPD21	Approved
0.6842	Remote Similarity	NPD4738	Phase 2
0.6842	Remote Similarity	NPD2048	Approved
0.6842	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5137	Approved
0.6842	Remote Similarity	NPD2045	Approved
0.6839	Remote Similarity	NPD5485	Approved
0.6839	Remote Similarity	NPD6073	Approved
0.6839	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5725	Approved
0.6839	Remote Similarity	NPD5484	Approved
0.6829	Remote Similarity	NPD2052	Approved
0.6828	Remote Similarity	NPD5303	Approved
0.6828	Remote Similarity	NPD5304	Approved
0.6828	Remote Similarity	NPD2218	Phase 2
0.6828	Remote Similarity	NPD2217	Approved
0.6826	Remote Similarity	NPD7318	Phase 3
0.6824	Remote Similarity	NPD2516	Approved
0.6821	Remote Similarity	NPD3626	Phase 3
0.6818	Remote Similarity	NPD8416	Discontinued
0.6818	Remote Similarity	NPD6623	Phase 3
0.6816	Remote Similarity	NPD4435	Approved
0.6815	Remote Similarity	NPD1537	Approved
0.6815	Remote Similarity	NPD1538	Phase 1
0.6815	Remote Similarity	NPD1519	Approved
0.6813	Remote Similarity	NPD3692	Discontinued
0.68	Remote Similarity	NPD1131	Approved
0.68	Remote Similarity	NPD1134	Approved
0.68	Remote Similarity	NPD1129	Approved
0.68	Remote Similarity	NPD1135	Approved
0.68	Remote Similarity	NPD1133	Approved
0.6797	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6852	Discontinued
0.6788	Remote Similarity	NPD2053	Approved
0.6788	Remote Similarity	NPD22	Approved
0.6779	Remote Similarity	NPD3685	Discontinued
0.6776	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2087	Approved
0.6772	Remote Similarity	NPD2022	Approved
0.6772	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8076	Discontinued
0.6772	Remote Similarity	NPD2088	Approved
0.6768	Remote Similarity	NPD8315	Phase 1
0.676	Remote Similarity	NPD4434	Approved
0.6757	Remote Similarity	NPD4807	Approved
0.6757	Remote Similarity	NPD4806	Approved
0.6757	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD2245	Discovery
0.6748	Remote Similarity	NPD5230	Approved
0.6748	Remote Similarity	NPD4731	Phase 3
0.6748	Remote Similarity	NPD5229	Approved
0.6733	Remote Similarity	NPD5367	Discontinued
0.6733	Remote Similarity	NPD196	Phase 1
0.6731	Remote Similarity	NPD2568	Approved
0.6731	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD2016	Approved
0.6728	Remote Similarity	NPD2014	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