NPASS Compound

Structure

NPC153554 OpenBabel07101718312D 61 63 0 0 1 0 0 0 0 0999 V2000 -1.0490 -1.1085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2721 -0.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4352 3.4181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3234 -2.0957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1894 -1.5957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4574 -1.5957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1230 5.6704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9448 5.1006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0596 8.2980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1894 -0.5957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4574 -0.5957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1608 5.9425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3239 7.6207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0384 -0.6526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0642 0.7430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3427 0.9335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8442 -1.2449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8700 0.1508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4269 0.5318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9548 4.3389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5370 4.2948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0140 7.9995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7267 3.7032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3234 0.9043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9939 -0.1100 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1484 0.3413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3234 -0.0957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7600 -0.8432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1623 5.8874 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0183 3.9883 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6211 1.1241 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3695 7.9192 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4574 1.4043 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9697 0.1087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8080 2.3408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7642 5.5111 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 0.9044 0.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1508 8.8950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7041 8.3783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6793 7.5405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9228 7.4025 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.4398 9.0555 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8356 3.3404 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.7497 8.6768 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5183 4.8543 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0727 2.0163 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8216 0.6323 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0564 6.8632 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6337 7.2420 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 6.5657 -1.4354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3460 -0.8178 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7895 2.1491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2879 6.3630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2096 3.0344 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4742 -0.3950 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8865 9.5723 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1964 9.1935 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4606 8.5163 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6633 4.0539 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2 51 1 0 0 0 0 3 61 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 21 1 0 0 0 0 9 13 1 0 0 0 0 9 22 1 0 0 0 0 10 27 2 0 0 0 0 11 27 1 0 0 0 0 12 29 1 0 0 0 0 14 17 1 0 0 0 0 14 26 2 0 0 0 0 15 18 2 0 0 0 0 15 26 1 0 0 0 0 16 19 1 0 0 0 0 16 26 1 0 0 0 0 17 28 2 0 0 0 0 18 28 1 0 0 0 0 20 23 1 0 0 0 0 21 44 1 0 0 0 0 22 45 1 0 0 0 0 23 61 1 0 0 0 0 24 27 1 0 0 0 0 25 1 1 1 0 0 0 25 34 1 0 0 0 0 25 51 1 0 0 0 0 28 52 1 0 0 0 0 29 36 1 0 0 0 0 29 49 1 1 0 0 0 30 20 1 1 0 0 0 30 37 1 0 0 0 0 30 46 1 0 0 0 0 31 19 1 1 0 0 0 31 38 1 0 0 0 0 31 47 1 0 0 0 0 32 13 1 1 0 0 0 32 39 1 0 0 0 0 32 50 1 0 0 0 0 33 24 1 1 0 0 0 33 35 1 0 0 0 0 33 48 1 0 0 0 0 34 48 2 3 0 0 0 34 53 1 0 0 0 0 35 44 2 3 0 0 0 35 54 1 0 0 0 0 36 46 2 3 0 0 0 36 55 1 0 0 0 0 37 47 2 3 0 0 0 37 56 1 0 0 0 0 38 51 1 0 0 0 0 38 57 2 0 0 0 0 39 58 2 0 0 0 0 39 59 1 0 0 0 0 40 42 2 0 0 0 0 40 43 1 0 0 0 0 40 45 1 0 0 0 0 41 49 2 3 0 0 0 41 50 1 0 0 0 0 41 60 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	868.43
Volume:	862.701
LogP:	-0.059
LogD:	0.445
LogS:	-3.558
# Rotatable Bonds:	18
TPSA:	300.76
# H-Bond Aceptor:	19
# H-Bond Donor:	12
# Rings:	3
# Heavy Atoms:	20

MedChem Properties

QED Drug-Likeness Score:	0.068
Synthetic Accessibility Score:	5.508
Fsp3:	0.512
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:	-6.906
MDCK Permeability:	4.6706395551154856e-06
Pgp-inhibitor:	0.04
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.919
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	41.94488525390625%
Volume Distribution (VD):	0.41
Pgp-substrate:	50.81727600097656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.029
CYP2C9-inhibitor:	0.173
CYP2C9-substrate:	0.158
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.164
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	1.629
Half-life (T1/2):	0.884

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.897
Drug-inuced Liver Injury (DILI):	0.904
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.309
Carcinogencity:	0.094
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.782

Download Data

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

Natural Product: NPC153554

Natural Product ID:	NPC153554
*Common Name:**	Oscillamide B
IUPAC Name:	(2S)-2-[[(3S,6S,9S,12S,15R)-3-benzyl-9-[2-(4-hydroxyphenyl)ethyl]-6,7-dimethyl-12-(2-methylsulfanylethyl)-2,5,8,11,14-pentaoxo-1,4,7,10,13-pentazacyclononadec-15-yl]carbamoylamino]-5-(diaminomethylideneamino)pentanoic acid
Synonyms:
Standard InCHIKey:	GGWYPJGDZASPSW-APNXPRSCSA-N
Standard InCHI:	InChI=1S/C41H60N10O9S/c1-25-34(53)48-33(24-27-10-5-4-6-11-27)35(54)44-21-8-7-12-29(49-41(60)50-32(39(58)59)13-9-22-45-40(42)43)36(55)46-30(20-23-61-3)37(56)47-31(38(57)51(25)2)19-16-26-14-17-28(52)18-15-26/h4-6,10-11,14-15,17-18,25,29-33,52H,7-9,12-13,16,19-24H2,1-3H3,(H,44,54)(H,46,55)(H,47,56)(H,48,53)(H,58,59)(H4,42,43,45)(H2,49,50,60)/t25-,29+,30-,31-,32-,33-/m0/s1
SMILES:	CSCC[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)C)O)Cc1ccccc1)O)N=C(N[C@H](C(=O)O)CCCNC(=N)N)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453299
PubChem CID:	10909100
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
NPO33422	planktothrix spp.	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11520225]

☑ 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	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	43.3	%	PMID[506156]
NPT2	Others	Unspecified		Inhibition	=	62.8	%	PMID[506156]

☑ 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 NPC153554 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	222
0.1-0.2	1829
0.2-0.3	11671
0.3-0.4	7034
0.4-0.5	18152
0.5-0.6	2944
0.6-0.7	568
0.7-0.8	225
0.8-0.85	39
0.85-0.9	8
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9441	High Similarity	NPC198254
0.9441	High Similarity	NPC274198
0.9321	High Similarity	NPC276506
0.9212	High Similarity	NPC196243
0.9006	High Similarity	NPC469243
0.8889	High Similarity	NPC475544
0.8841	High Similarity	NPC223207
0.8788	High Similarity	NPC304074
0.8788	High Similarity	NPC471771
0.8788	High Similarity	NPC290755
0.8758	High Similarity	NPC473580
0.8639	High Similarity	NPC475532
0.8588	High Similarity	NPC165285
0.848	Intermediate Similarity	NPC17698
0.8462	Intermediate Similarity	NPC129486
0.8427	Intermediate Similarity	NPC240130
0.8427	Intermediate Similarity	NPC61332
0.8396	Intermediate Similarity	NPC478005
0.8389	Intermediate Similarity	NPC302715
0.8343	Intermediate Similarity	NPC477638
0.8343	Intermediate Similarity	NPC477632
0.8343	Intermediate Similarity	NPC473404
0.8246	Intermediate Similarity	NPC280022
0.8167	Intermediate Similarity	NPC102959
0.8122	Intermediate Similarity	NPC60516
0.8122	Intermediate Similarity	NPC477636
0.8111	Intermediate Similarity	NPC94862
0.8098	Intermediate Similarity	NPC477639
0.807	Intermediate Similarity	NPC63931
0.8063	Intermediate Similarity	NPC48202
0.8033	Intermediate Similarity	NPC477631
0.8023	Intermediate Similarity	NPC119652
0.8023	Intermediate Similarity	NPC97526
0.802	Intermediate Similarity	NPC478007
0.8	Intermediate Similarity	NPC306804
0.7988	Intermediate Similarity	NPC16188
0.7988	Intermediate Similarity	NPC326349
0.7988	Intermediate Similarity	NPC323336
0.7964	Intermediate Similarity	NPC202198
0.794	Intermediate Similarity	NPC478008
0.7919	Intermediate Similarity	NPC61004
0.7904	Intermediate Similarity	NPC233702
0.7903	Intermediate Similarity	NPC329295
0.7888	Intermediate Similarity	NPC132636
0.7886	Intermediate Similarity	NPC46009
0.7874	Intermediate Similarity	NPC328649
0.7849	Intermediate Similarity	NPC241794
0.7821	Intermediate Similarity	NPC194671
0.7821	Intermediate Similarity	NPC269750
0.7819	Intermediate Similarity	NPC477550
0.7819	Intermediate Similarity	NPC477552
0.7812	Intermediate Similarity	NPC267237
0.7797	Intermediate Similarity	NPC137627
0.7753	Intermediate Similarity	NPC279871
0.7753	Intermediate Similarity	NPC26108
0.7737	Intermediate Similarity	NPC477551
0.7727	Intermediate Similarity	NPC315388
0.7709	Intermediate Similarity	NPC50016
0.7697	Intermediate Similarity	NPC273755
0.7684	Intermediate Similarity	NPC475204
0.7684	Intermediate Similarity	NPC475123
0.7683	Intermediate Similarity	NPC476989
0.768	Intermediate Similarity	NPC475564
0.768	Intermediate Similarity	NPC170302
0.768	Intermediate Similarity	NPC475409
0.767	Intermediate Similarity	NPC107938
0.767	Intermediate Similarity	NPC141957
0.767	Intermediate Similarity	NPC294516
0.7665	Intermediate Similarity	NPC311658
0.7654	Intermediate Similarity	NPC159767
0.7654	Intermediate Similarity	NPC155506
0.7647	Intermediate Similarity	NPC5194
0.7647	Intermediate Similarity	NPC56685
0.7647	Intermediate Similarity	NPC261934
0.7644	Intermediate Similarity	NPC469443
0.7641	Intermediate Similarity	NPC469444
0.764	Intermediate Similarity	NPC230611
0.7637	Intermediate Similarity	NPC477637
0.7627	Intermediate Similarity	NPC66490
0.7624	Intermediate Similarity	NPC45037
0.7622	Intermediate Similarity	NPC214988
0.7584	Intermediate Similarity	NPC40234
0.7578	Intermediate Similarity	NPC326966
0.7569	Intermediate Similarity	NPC473546
0.7562	Intermediate Similarity	NPC325651
0.7556	Intermediate Similarity	NPC471165
0.7556	Intermediate Similarity	NPC473402
0.7556	Intermediate Similarity	NPC476227
0.7544	Intermediate Similarity	NPC262166
0.7542	Intermediate Similarity	NPC89831
0.7529	Intermediate Similarity	NPC473491
0.7529	Intermediate Similarity	NPC244336
0.7525	Intermediate Similarity	NPC469445
0.75	Intermediate Similarity	NPC220060
0.75	Intermediate Similarity	NPC248670
0.7472	Intermediate Similarity	NPC302597
0.7459	Intermediate Similarity	NPC294951
0.7459	Intermediate Similarity	NPC473354
0.7455	Intermediate Similarity	NPC242159
0.7455	Intermediate Similarity	NPC313694
0.7433	Intermediate Similarity	NPC329731
0.7433	Intermediate Similarity	NPC4910
0.7429	Intermediate Similarity	NPC319320
0.7429	Intermediate Similarity	NPC287757
0.7382	Intermediate Similarity	NPC184933
0.7382	Intermediate Similarity	NPC59827
0.7374	Intermediate Similarity	NPC209463
0.7371	Intermediate Similarity	NPC473450
0.7371	Intermediate Similarity	NPC324850
0.7366	Intermediate Similarity	NPC471050
0.7366	Intermediate Similarity	NPC471048
0.7366	Intermediate Similarity	NPC471049
0.7362	Intermediate Similarity	NPC257390
0.7356	Intermediate Similarity	NPC244509
0.7354	Intermediate Similarity	NPC473305
0.7354	Intermediate Similarity	NPC163961
0.7351	Intermediate Similarity	NPC476321
0.734	Intermediate Similarity	NPC96275
0.7333	Intermediate Similarity	NPC314835
0.733	Intermediate Similarity	NPC1390
0.733	Intermediate Similarity	NPC62104
0.7326	Intermediate Similarity	NPC235194
0.7321	Intermediate Similarity	NPC168861
0.7317	Intermediate Similarity	NPC244866
0.7316	Intermediate Similarity	NPC477526
0.7312	Intermediate Similarity	NPC471526
0.7294	Intermediate Similarity	NPC81026
0.7288	Intermediate Similarity	NPC114806
0.7268	Intermediate Similarity	NPC477527
0.7268	Intermediate Similarity	NPC136797
0.7268	Intermediate Similarity	NPC158277
0.7267	Intermediate Similarity	NPC477937
0.7263	Intermediate Similarity	NPC51047
0.7263	Intermediate Similarity	NPC5719
0.7263	Intermediate Similarity	NPC22883
0.7263	Intermediate Similarity	NPC217804
0.7263	Intermediate Similarity	NPC210377
0.7257	Intermediate Similarity	NPC476268
0.7236	Intermediate Similarity	NPC194699
0.7236	Intermediate Similarity	NPC219350
0.7235	Intermediate Similarity	NPC266741
0.7232	Intermediate Similarity	NPC24617
0.7222	Intermediate Similarity	NPC15068
0.7211	Intermediate Similarity	NPC234069
0.7209	Intermediate Similarity	NPC105717
0.7193	Intermediate Similarity	NPC314114
0.7184	Intermediate Similarity	NPC300443
0.7182	Intermediate Similarity	NPC63040
0.7178	Intermediate Similarity	NPC469442
0.7178	Intermediate Similarity	NPC277306
0.7173	Intermediate Similarity	NPC174122
0.7173	Intermediate Similarity	NPC64140
0.7143	Intermediate Similarity	NPC138083
0.7143	Intermediate Similarity	NPC299806
0.7134	Intermediate Similarity	NPC300315
0.7126	Intermediate Similarity	NPC324081
0.7125	Intermediate Similarity	NPC27581
0.712	Intermediate Similarity	NPC246591
0.7113	Intermediate Similarity	NPC80514
0.7112	Intermediate Similarity	NPC32064
0.7109	Intermediate Similarity	NPC323244
0.7108	Intermediate Similarity	NPC25539
0.7102	Intermediate Similarity	NPC39431
0.7081	Intermediate Similarity	NPC164608
0.7076	Intermediate Similarity	NPC326241
0.7072	Intermediate Similarity	NPC472923
0.7062	Intermediate Similarity	NPC328763
0.7047	Intermediate Similarity	NPC248822
0.7047	Intermediate Similarity	NPC473378
0.7047	Intermediate Similarity	NPC473407
0.7047	Intermediate Similarity	NPC470728
0.7045	Intermediate Similarity	NPC286551
0.7017	Intermediate Similarity	NPC289776
0.7017	Intermediate Similarity	NPC191863
0.7017	Intermediate Similarity	NPC133470
0.6977	Remote Similarity	NPC328924
0.6974	Remote Similarity	NPC65714
0.6973	Remote Similarity	NPC328494
0.6971	Remote Similarity	NPC13470
0.697	Remote Similarity	NPC111428
0.6966	Remote Similarity	NPC469903
0.6963	Remote Similarity	NPC315542
0.6957	Remote Similarity	NPC186617
0.6957	Remote Similarity	NPC71684
0.6949	Remote Similarity	NPC473341
0.6949	Remote Similarity	NPC122590
0.6937	Remote Similarity	NPC319950
0.6936	Remote Similarity	NPC322878
0.6931	Remote Similarity	NPC246303
0.6927	Remote Similarity	NPC276120
0.6919	Remote Similarity	NPC196091
0.6919	Remote Similarity	NPC91953
0.6919	Remote Similarity	NPC471568
0.6919	Remote Similarity	NPC473693
0.6919	Remote Similarity	NPC468984
0.6919	Remote Similarity	NPC323662
0.6906	Remote Similarity	NPC469902
0.6904	Remote Similarity	NPC473371
0.6902	Remote Similarity	NPC473502
0.6898	Remote Similarity	NPC326407

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 NPC153554 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	423
0.2-0.3	990
0.3-0.4	1419
0.4-0.5	3919
0.5-0.6	1909
0.6-0.7	319
0.7-0.8	33
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8675	High Similarity	NPD8303	Discontinued
0.8485	Intermediate Similarity	NPD7495	Discontinued
0.8373	Intermediate Similarity	NPD8019	Approved
0.8232	Intermediate Similarity	NPD7303	Discontinued
0.8182	Intermediate Similarity	NPD7523	Phase 3
0.8063	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD4652	Approved
0.7861	Intermediate Similarity	NPD2098	Approved
0.7746	Intermediate Similarity	NPD2097	Approved
0.773	Intermediate Similarity	NPD7617	Discontinued
0.7727	Intermediate Similarity	NPD2888	Approved
0.7727	Intermediate Similarity	NPD2890	Approved
0.7727	Intermediate Similarity	NPD2017	Approved
0.7727	Intermediate Similarity	NPD2889	Approved
0.7674	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD8076	Discontinued
0.7485	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7450	Phase 2
0.7459	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6901	Phase 3
0.7399	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6254	Approved
0.7333	Intermediate Similarity	NPD6255	Approved
0.7333	Intermediate Similarity	NPD6256	Approved
0.731	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6253	Approved
0.7267	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6189	Approved
0.7192	Intermediate Similarity	NPD6188	Approved
0.7186	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD5323	Approved
0.7169	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6187	Approved
0.7118	Intermediate Similarity	NPD7978	Discontinued
0.7091	Intermediate Similarity	NPD3136	Phase 2
0.7073	Intermediate Similarity	NPD7828	Discontinued
0.7069	Intermediate Similarity	NPD5613	Approved
0.7069	Intermediate Similarity	NPD5614	Approved
0.7068	Intermediate Similarity	NPD6089	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7484	Phase 3
0.7049	Intermediate Similarity	NPD7485	Phase 3
0.7048	Intermediate Similarity	NPD5299	Approved
0.7045	Intermediate Similarity	NPD7131	Phase 3
0.7041	Intermediate Similarity	NPD4126	Approved
0.703	Intermediate Similarity	NPD4125	Approved
0.6994	Remote Similarity	NPD5367	Discontinued
0.6971	Remote Similarity	NPD2013	Approved
0.6971	Remote Similarity	NPD3987	Approved
0.6971	Remote Similarity	NPD2014	Approved
0.6971	Remote Similarity	NPD2016	Approved
0.6971	Remote Similarity	NPD3988	Approved
0.6968	Remote Similarity	NPD5484	Approved
0.6968	Remote Similarity	NPD5485	Approved
0.6952	Remote Similarity	NPD6796	Discontinued
0.6951	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2087	Approved
0.6919	Remote Similarity	NPD7608	Discontinued
0.6919	Remote Similarity	NPD2088	Approved
0.6909	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4567	Approved
0.6906	Remote Similarity	NPD4566	Approved
0.6893	Remote Similarity	NPD6390	Discontinued
0.6882	Remote Similarity	NPD5137	Approved
0.6878	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD8292	Phase 2
0.6862	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1330	Phase 2
0.6842	Remote Similarity	NPD6297	Approved
0.6839	Remote Similarity	NPD5265	Approved
0.6839	Remote Similarity	NPD5264	Approved
0.6832	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3908	Approved
0.6807	Remote Similarity	NPD7451	Discontinued
0.6807	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6853	Approved
0.6788	Remote Similarity	NPD6851	Approved
0.6786	Remote Similarity	NPD6504	Approved
0.6786	Remote Similarity	NPD6505	Approved
0.6768	Remote Similarity	NPD3072	Approved
0.6768	Remote Similarity	NPD3071	Approved
0.6768	Remote Similarity	NPD3073	Approved
0.6758	Remote Similarity	NPD5356	Approved
0.6758	Remote Similarity	NPD5355	Approved
0.6754	Remote Similarity	NPD5445	Approved
0.675	Remote Similarity	NPD9568	Approved
0.6743	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.674	Remote Similarity	NPD2891	Approved
0.6734	Remote Similarity	NPD3659	Discontinued
0.6731	Remote Similarity	NPD3879	Approved
0.6728	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5263	Approved
0.6724	Remote Similarity	NPD2022	Approved
0.6718	Remote Similarity	NPD3919	Approved
0.6707	Remote Similarity	NPD4761	Approved
0.6707	Remote Similarity	NPD4762	Approved
0.6705	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3125	Approved
0.6686	Remote Similarity	NPD2048	Approved
0.6686	Remote Similarity	NPD2044	Approved
0.6686	Remote Similarity	NPD2047	Approved
0.6686	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD21	Approved
0.6686	Remote Similarity	NPD2046	Approved
0.6686	Remote Similarity	NPD2045	Approved
0.6686	Remote Similarity	NPD2043	Approved
0.6686	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2051	Approved
0.6686	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD1582	Approved
0.6685	Remote Similarity	NPD1581	Approved
0.6685	Remote Similarity	NPD5967	Approved
0.6683	Remote Similarity	NPD3878	Approved
0.6667	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD2853	Approved
0.6628	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD4677	Discontinued
0.6618	Remote Similarity	NPD8162	Phase 2
0.6618	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD8031	Discontinued
0.6611	Remote Similarity	NPD5230	Approved
0.6611	Remote Similarity	NPD5229	Approved
0.6611	Remote Similarity	NPD7613	Discontinued
0.661	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6865	Phase 2
0.6609	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6864	Phase 2
0.6599	Remote Similarity	NPD4435	Approved
0.6591	Remote Similarity	NPD2437	Approved
0.6591	Remote Similarity	NPD2436	Approved
0.6591	Remote Similarity	NPD6681	Discovery
0.659	Remote Similarity	NPD6073	Approved
0.6575	Remote Similarity	NPD4090	Discontinued
0.657	Remote Similarity	NPD6346	Approved
0.6568	Remote Similarity	NPD4177	Approved
0.6568	Remote Similarity	NPD4175	Approved
0.6568	Remote Similarity	NPD3040	Approved
0.6566	Remote Similarity	NPD2562	Approved
0.6566	Remote Similarity	NPD2561	Approved
0.6561	Remote Similarity	NPD2517	Approved
0.6554	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.655	Remote Similarity	NPD5581	Approved
0.6548	Remote Similarity	NPD4434	Approved
0.6538	Remote Similarity	NPD4646	Approved
0.6538	Remote Similarity	NPD4647	Approved
0.6538	Remote Similarity	NPD4648	Approved
0.6536	Remote Similarity	NPD3509	Approved
0.6536	Remote Similarity	NPD3510	Approved
0.6529	Remote Similarity	NPD4676	Approved
0.6522	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD1968	Approved
0.6517	Remote Similarity	NPD1967	Approved
0.6515	Remote Similarity	NPD5852	Approved
0.6515	Remote Similarity	NPD5851	Approved
0.6509	Remote Similarity	NPD4151	Approved
0.6508	Remote Similarity	NPD2516	Approved
0.6506	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6088	Approved
0.6497	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD256	Approved
0.6481	Remote Similarity	NPD255	Approved
0.648	Remote Similarity	NPD7740	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6623	Phase 3
0.6471	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD9569	Approved
0.6462	Remote Similarity	NPD2852	Approved
0.6457	Remote Similarity	NPD3554	Approved
0.6457	Remote Similarity	NPD3553	Approved
0.6457	Remote Similarity	NPD3552	Approved
0.6457	Remote Similarity	NPD3555	Approved
0.6452	Remote Similarity	NPD4557	Approved
0.645	Remote Similarity	NPD3053	Approved
0.645	Remote Similarity	NPD3055	Approved
0.6444	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7554	Discontinued
0.6441	Remote Similarity	NPD7720	Phase 2
0.6429	Remote Similarity	NPD5638	Approved
0.6425	Remote Similarity	NPD3400	Discontinued
0.642	Remote Similarity	NPD3480	Approved
0.6418	Remote Similarity	NPD3479	Discontinued
0.6417	Remote Similarity	NPD6646	Discontinued
0.6416	Remote Similarity	NPD259	Phase 1
0.6416	Remote Similarity	NPD5745	Approved
0.6414	Remote Similarity	NPD6967	Phase 2
0.6409	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2568	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