NPASS Compound

Structure

CID163924 OpenBabel06191715532D 46 48 0 0 1 0 0 0 0 0999 V2000 -3.4408 0.6882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1320 -4.1965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3688 -5.1366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9950 -0.4031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1965 -0.6207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4408 -3.4408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1965 -2.1320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6593 -3.1428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8801 0.5038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3763 0.5701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3496 0.3093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8726 0.5038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3763 -3.3228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7527 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8801 -3.2565 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8726 -3.2565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1522 -0.8897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2565 -0.8726 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7527 -2.7527 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2565 -1.8801 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8246 -2.6423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4031 0.3093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3093 -2.3496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.7527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5335 -1.8629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3093 -0.4031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0620 -0.4031 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3496 -3.0620 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4031 -3.0620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3228 -1.3763 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0620 -2.3496 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1522 -1.8629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4389 -2.8960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8667 -2.1825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5335 -0.8897 0.0000 C 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 0.0835 1.1522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9048 0.0835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8362 -3.9048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0835 -3.9048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2960 -1.3763 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9048 -2.8362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9950 -2.3496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5680 -3.8607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7784 -1.8420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3763 -0.4031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 11 2 0 0 0 0 10 12 2 0 0 0 0 11 14 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 16 2 0 0 0 0 14 1 1 1 0 0 0 14 27 1 0 0 0 0 15 2 1 6 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 26 2 0 0 0 0 17 32 1 0 0 0 0 18 5 1 6 0 0 0 18 27 1 0 0 0 0 18 30 1 0 0 0 0 19 6 1 1 0 0 0 19 28 1 0 0 0 0 19 31 1 0 0 0 0 20 7 1 6 0 0 0 20 30 1 0 0 0 0 20 31 1 0 0 0 0 21 33 2 0 0 0 0 21 34 1 0 0 0 0 22 36 2 3 0 0 0 22 37 1 0 0 0 0 23 24 2 0 0 0 0 23 25 1 0 0 0 0 23 32 1 0 0 0 0 24 29 1 0 0 0 0 24 33 1 0 0 0 0 25 34 2 0 0 0 0 25 35 1 0 0 0 0 26 35 1 0 0 0 0 26 36 1 0 0 0 0 27 38 1 1 0 0 0 28 39 1 6 0 0 0 29 40 2 0 0 0 0 30 41 1 6 0 0 0 31 42 1 1 0 0 0 32 43 2 0 0 0 0 33 44 1 0 0 0 0 34 45 1 0 0 0 0 35 46 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	639.3
Volume:	658.145
LogP:	4.342
LogD:	1.999
LogS:	-2.975
# Rotatable Bonds:	0
TPSA:	208.34
# H-Bond Aceptor:	11
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.197
Synthetic Accessibility Score:	6.85
Fsp3:	0.457
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.997
MDCK Permeability:	3.4045347092614975e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.984
Human Intestinal Absorption (HIA):	0.375
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	93.11226654052734%
Volume Distribution (VD):	0.796
Pgp-substrate:	9.375633239746094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.328
CYP1A2-substrate:	0.656
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.511
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.19
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.096
CYP3A4-substrate:	0.213

ADMET: Excretion

Clearance (CL):	1.516
Half-life (T1/2):	0.82

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.703
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.46
Rat Oral Acute Toxicity:	0.196
Maximum Recommended Daily Dose:	0.844
Skin Sensitization:	0.941
Carcinogencity:	0.208
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.863

Download Data

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

Natural Product: NPC163924

Natural Product ID:	NPC163924
*Common Name:**	Chaxamycin A
IUPAC Name:	n.a.
Synonyms:	Chaxamycin A
Standard InCHIKey:	OWRAZHDHNJAEKU-NMCWGSMOSA-N
Standard InCHI:	InChI=1S/C35H45NO10/c1-14-11-9-10-12-22(37)36-26-17(4)32(43)23-24(33(44)21(8)34(45)25(23)35(26)46)29(40)16(3)13-15(2)28(39)19(6)31(42)20(7)30(41)18(5)27(14)38/h9-15,18-20,27-28,30-31,38-39,41-42,44-45H,1-8H3,(H,36,37)/b11-9+,12-10-,16-13+/t14-,15-,18+,19+,20+,27-,28-,30+,31+/m0/s1
SMILES:	OC1=NC2=C(C)C(=O)c3c(C2=O)c(O)c(c(c3C(=O)/C(=C/[C@H](C)[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]([C@H](/C=C/C=C1)C)O)C)O)C)O)C)O)/C)O)C
Synthetic Gene Cluster:	BGC0001287;
ChEMBL Identifier:	CHEMBL1814384
PubChem CID:	53344650
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000064] Macrolactams

*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
NPO31293	Streptomyces sp. c34	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21553813]

☑ 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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT918	Individual Protein	Heat shock protein HSP 90-alpha	Homo sapiens	Inhibition	=	46.0	%	PMID[551423]

☑ 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 NPC163924 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	259
0.1-0.2	1169
0.2-0.3	3578
0.3-0.4	10904
0.4-0.5	9112
0.5-0.6	10241
0.6-0.7	6731
0.7-0.8	688
0.8-0.85	6
0.85-0.9	6
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC54661
0.9554	High Similarity	NPC101207
0.9012	High Similarity	NPC314693
0.8902	High Similarity	NPC12890
0.8529	High Similarity	NPC313708
0.8521	High Similarity	NPC315406
0.8492	Intermediate Similarity	NPC313453
0.7937	Intermediate Similarity	NPC162939
0.7901	Intermediate Similarity	NPC135524
0.7901	Intermediate Similarity	NPC193555
0.784	Intermediate Similarity	NPC204045
0.784	Intermediate Similarity	NPC305845
0.7811	Intermediate Similarity	NPC96160
0.7811	Intermediate Similarity	NPC4331
0.7791	Intermediate Similarity	NPC474961
0.7778	Intermediate Similarity	NPC181560
0.7778	Intermediate Similarity	NPC169452
0.7716	Intermediate Similarity	NPC242994
0.7716	Intermediate Similarity	NPC138099
0.7702	Intermediate Similarity	NPC238108
0.7697	Intermediate Similarity	NPC471906
0.7697	Intermediate Similarity	NPC244691
0.7683	Intermediate Similarity	NPC73061
0.7651	Intermediate Similarity	NPC34482
0.7625	Intermediate Similarity	NPC282780
0.7625	Intermediate Similarity	NPC474519
0.7625	Intermediate Similarity	NPC166480
0.7609	Intermediate Similarity	NPC70340
0.7607	Intermediate Similarity	NPC190457
0.7605	Intermediate Similarity	NPC110882
0.7605	Intermediate Similarity	NPC271944
0.7605	Intermediate Similarity	NPC85393
0.7605	Intermediate Similarity	NPC470570
0.7593	Intermediate Similarity	NPC53414
0.7593	Intermediate Similarity	NPC53206
0.7593	Intermediate Similarity	NPC471905
0.759	Intermediate Similarity	NPC193703
0.759	Intermediate Similarity	NPC48762
0.759	Intermediate Similarity	NPC21599
0.7578	Intermediate Similarity	NPC290803
0.7574	Intermediate Similarity	NPC477221
0.7531	Intermediate Similarity	NPC315275
0.7531	Intermediate Similarity	NPC191976
0.7531	Intermediate Similarity	NPC254847
0.7531	Intermediate Similarity	NPC86524
0.7516	Intermediate Similarity	NPC474394
0.7515	Intermediate Similarity	NPC187843
0.7514	Intermediate Similarity	NPC474861
0.75	Intermediate Similarity	NPC314437
0.75	Intermediate Similarity	NPC472211
0.75	Intermediate Similarity	NPC143685
0.7485	Intermediate Similarity	NPC471452
0.7485	Intermediate Similarity	NPC470569
0.7473	Intermediate Similarity	NPC477816
0.747	Intermediate Similarity	NPC137649
0.747	Intermediate Similarity	NPC291078
0.7453	Intermediate Similarity	NPC180261
0.7453	Intermediate Similarity	NPC40524
0.7453	Intermediate Similarity	NPC139074
0.7453	Intermediate Similarity	NPC37299
0.7453	Intermediate Similarity	NPC48036
0.7453	Intermediate Similarity	NPC213485
0.7439	Intermediate Similarity	NPC472403
0.7439	Intermediate Similarity	NPC177307
0.7439	Intermediate Similarity	NPC9121
0.7439	Intermediate Similarity	NPC87723
0.7439	Intermediate Similarity	NPC123714
0.7439	Intermediate Similarity	NPC475974
0.7438	Intermediate Similarity	NPC475042
0.7427	Intermediate Similarity	NPC255641
0.7427	Intermediate Similarity	NPC290954
0.7427	Intermediate Similarity	NPC470568
0.7423	Intermediate Similarity	NPC118919
0.7412	Intermediate Similarity	NPC112816
0.741	Intermediate Similarity	NPC246638
0.741	Intermediate Similarity	NPC290550
0.7407	Intermediate Similarity	NPC44437
0.7405	Intermediate Similarity	NPC329205
0.7405	Intermediate Similarity	NPC316625
0.7399	Intermediate Similarity	NPC208806
0.7399	Intermediate Similarity	NPC218870
0.7399	Intermediate Similarity	NPC155686
0.7399	Intermediate Similarity	NPC182921
0.7399	Intermediate Similarity	NPC474824
0.7399	Intermediate Similarity	NPC470408
0.7396	Intermediate Similarity	NPC136878
0.7394	Intermediate Similarity	NPC143438
0.7391	Intermediate Similarity	NPC246693
0.7391	Intermediate Similarity	NPC242358
0.7391	Intermediate Similarity	NPC175738
0.7391	Intermediate Similarity	NPC110609
0.7384	Intermediate Similarity	NPC46882
0.7384	Intermediate Similarity	NPC132990
0.7381	Intermediate Similarity	NPC42540
0.7381	Intermediate Similarity	NPC151607
0.7378	Intermediate Similarity	NPC474771
0.7378	Intermediate Similarity	NPC149372
0.7378	Intermediate Similarity	NPC65837
0.7378	Intermediate Similarity	NPC53001
0.7378	Intermediate Similarity	NPC178467
0.7378	Intermediate Similarity	NPC474849
0.7375	Intermediate Similarity	NPC259942
0.7375	Intermediate Similarity	NPC147757
0.7375	Intermediate Similarity	NPC62219
0.7371	Intermediate Similarity	NPC474637
0.7366	Intermediate Similarity	NPC314987
0.7365	Intermediate Similarity	NPC476508
0.7362	Intermediate Similarity	NPC61153
0.7362	Intermediate Similarity	NPC236795
0.7362	Intermediate Similarity	NPC278375
0.7362	Intermediate Similarity	NPC283590
0.7362	Intermediate Similarity	NPC130899
0.7362	Intermediate Similarity	NPC70859
0.7362	Intermediate Similarity	NPC475917
0.7353	Intermediate Similarity	NPC290194
0.7353	Intermediate Similarity	NPC37709
0.7349	Intermediate Similarity	NPC156872
0.7349	Intermediate Similarity	NPC183345
0.7346	Intermediate Similarity	NPC115458
0.7346	Intermediate Similarity	NPC267205
0.7342	Intermediate Similarity	NPC473691
0.7342	Intermediate Similarity	NPC328983
0.7341	Intermediate Similarity	NPC470340
0.7337	Intermediate Similarity	NPC132751
0.7333	Intermediate Similarity	NPC4214
0.7333	Intermediate Similarity	NPC13715
0.733	Intermediate Similarity	NPC324736
0.7329	Intermediate Similarity	NPC275504
0.7329	Intermediate Similarity	NPC17083
0.7326	Intermediate Similarity	NPC280295
0.7326	Intermediate Similarity	NPC48949
0.7326	Intermediate Similarity	NPC147735
0.7321	Intermediate Similarity	NPC451542
0.7321	Intermediate Similarity	NPC478202
0.7321	Intermediate Similarity	NPC295712
0.7321	Intermediate Similarity	NPC293545
0.7321	Intermediate Similarity	NPC474203
0.7321	Intermediate Similarity	NPC159721
0.7321	Intermediate Similarity	NPC313047
0.7321	Intermediate Similarity	NPC174905
0.7321	Intermediate Similarity	NPC471731
0.7312	Intermediate Similarity	NPC109123
0.7312	Intermediate Similarity	NPC73203
0.7312	Intermediate Similarity	NPC92624
0.7305	Intermediate Similarity	NPC478217
0.7305	Intermediate Similarity	NPC478201
0.7305	Intermediate Similarity	NPC313123
0.7305	Intermediate Similarity	NPC472035
0.7303	Intermediate Similarity	NPC315772
0.7301	Intermediate Similarity	NPC474117
0.7301	Intermediate Similarity	NPC474224
0.7301	Intermediate Similarity	NPC270899
0.7301	Intermediate Similarity	NPC475088
0.7299	Intermediate Similarity	NPC471695
0.7297	Intermediate Similarity	NPC288854
0.7289	Intermediate Similarity	NPC474655
0.7284	Intermediate Similarity	NPC478190
0.7284	Intermediate Similarity	NPC58685
0.7283	Intermediate Similarity	NPC35
0.7278	Intermediate Similarity	NPC475201
0.7278	Intermediate Similarity	NPC477454
0.7273	Intermediate Similarity	NPC245058
0.7273	Intermediate Similarity	NPC71256
0.7273	Intermediate Similarity	NPC263483
0.7273	Intermediate Similarity	NPC475957
0.7273	Intermediate Similarity	NPC470989
0.7273	Intermediate Similarity	NPC470985
0.7267	Intermediate Similarity	NPC247477
0.7267	Intermediate Similarity	NPC17840
0.7267	Intermediate Similarity	NPC31799
0.7262	Intermediate Similarity	NPC471733
0.7262	Intermediate Similarity	NPC469520
0.7261	Intermediate Similarity	NPC306288
0.7257	Intermediate Similarity	NPC66508
0.7257	Intermediate Similarity	NPC226656
0.7256	Intermediate Similarity	NPC161632
0.7256	Intermediate Similarity	NPC283088
0.7256	Intermediate Similarity	NPC249272
0.7253	Intermediate Similarity	NPC221792
0.7251	Intermediate Similarity	NPC190648
0.7251	Intermediate Similarity	NPC8817
0.7251	Intermediate Similarity	NPC289042
0.7251	Intermediate Similarity	NPC312929
0.7251	Intermediate Similarity	NPC245584
0.7251	Intermediate Similarity	NPC137296
0.7251	Intermediate Similarity	NPC126767
0.7251	Intermediate Similarity	NPC56433
0.7251	Intermediate Similarity	NPC118027
0.725	Intermediate Similarity	NPC179898
0.725	Intermediate Similarity	NPC473017
0.725	Intermediate Similarity	NPC24869
0.7246	Intermediate Similarity	NPC315578
0.7241	Intermediate Similarity	NPC154683
0.7241	Intermediate Similarity	NPC40356
0.7239	Intermediate Similarity	NPC114183
0.7239	Intermediate Similarity	NPC53896
0.7239	Intermediate Similarity	NPC52407
0.7239	Intermediate Similarity	NPC254603
0.7238	Intermediate Similarity	NPC472058
0.7238	Intermediate Similarity	NPC324522

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 NPC163924 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	696
0.2-0.3	1255
0.3-0.4	2587
0.4-0.5	2934
0.5-0.6	1248
0.6-0.7	219
0.7-0.8	22
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
0.7531	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD8469	Approved
0.7291	Intermediate Similarity	NPD8366	Approved
0.7283	Intermediate Similarity	NPD5035	Approved
0.7176	Intermediate Similarity	NPD7390	Discontinued
0.7166	Intermediate Similarity	NPD8150	Discontinued
0.715	Intermediate Similarity	NPD8491	Approved
0.7135	Intermediate Similarity	NPD2533	Approved
0.7135	Intermediate Similarity	NPD2534	Approved
0.7135	Intermediate Similarity	NPD2532	Approved
0.7085	Intermediate Similarity	NPD8151	Discontinued
0.7062	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD4955	Approved
0.7043	Intermediate Similarity	NPD36	Approved
0.7043	Intermediate Similarity	NPD4954	Approved
0.7043	Intermediate Similarity	NPD5026	Approved
0.7043	Intermediate Similarity	NPD5034	Approved
0.7043	Intermediate Similarity	NPD5028	Approved
0.7017	Intermediate Similarity	NPD5710	Approved
0.7017	Intermediate Similarity	NPD5711	Approved
0.7006	Intermediate Similarity	NPD7819	Suspended
0.6995	Remote Similarity	NPD7473	Discontinued
0.6989	Remote Similarity	NPD5030	Phase 2
0.6984	Remote Similarity	NPD5037	Approved
0.6984	Remote Similarity	NPD5038	Approved
0.6973	Remote Similarity	NPD4956	Approved
0.6939	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7801	Approved
0.6931	Remote Similarity	NPD5036	Approved
0.6901	Remote Similarity	NPD3400	Discontinued
0.6898	Remote Similarity	NPD5039	Approved
0.6891	Remote Similarity	NPD6212	Phase 3
0.6891	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6213	Phase 3
0.6886	Remote Similarity	NPD6651	Approved
0.6867	Remote Similarity	NPD943	Approved
0.6864	Remote Similarity	NPD5404	Approved
0.6864	Remote Similarity	NPD5406	Approved
0.6864	Remote Similarity	NPD5408	Approved
0.6864	Remote Similarity	NPD5405	Approved
0.6862	Remote Similarity	NPD5032	Approved
0.6862	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD8067	Phase 3
0.6852	Remote Similarity	NPD1470	Approved
0.6837	Remote Similarity	NPD7700	Phase 2
0.6837	Remote Similarity	NPD7699	Phase 2
0.6831	Remote Similarity	NPD6232	Discontinued
0.6828	Remote Similarity	NPD6020	Phase 2
0.6821	Remote Similarity	NPD3300	Phase 2
0.6805	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.68	Remote Similarity	NPD8319	Approved
0.68	Remote Similarity	NPD8320	Phase 1
0.6798	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7874	Approved
0.6776	Remote Similarity	NPD6959	Discontinued
0.6769	Remote Similarity	NPD6534	Approved
0.6769	Remote Similarity	NPD6535	Approved
0.6753	Remote Similarity	NPD5968	Phase 3
0.6743	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4380	Phase 2
0.672	Remote Similarity	NPD5029	Approved
0.672	Remote Similarity	NPD5027	Approved
0.672	Remote Similarity	NPD5031	Approved
0.6686	Remote Similarity	NPD1607	Approved
0.6686	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7696	Phase 3
0.6667	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD7697	Approved
0.665	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7584	Approved
0.6649	Remote Similarity	NPD6836	Approved
0.6647	Remote Similarity	NPD2800	Approved
0.6646	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7870	Phase 2
0.6634	Remote Similarity	NPD7871	Phase 2
0.6632	Remote Similarity	NPD6104	Discontinued
0.6631	Remote Similarity	NPD5033	Approved
0.663	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7701	Phase 2
0.6617	Remote Similarity	NPD6823	Phase 2
0.6612	Remote Similarity	NPD7075	Discontinued
0.6611	Remote Similarity	NPD7411	Suspended
0.6608	Remote Similarity	NPD1510	Phase 2
0.6605	Remote Similarity	NPD1201	Approved
0.66	Remote Similarity	NPD6781	Approved
0.66	Remote Similarity	NPD6782	Approved
0.66	Remote Similarity	NPD6776	Approved
0.66	Remote Similarity	NPD6778	Approved
0.66	Remote Similarity	NPD6780	Approved
0.66	Remote Similarity	NPD6779	Approved
0.66	Remote Similarity	NPD6777	Approved
0.6596	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD3226	Approved
0.6582	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD1240	Approved
0.6554	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD7282	Approved
0.6528	Remote Similarity	NPD7654	Discontinued
0.6517	Remote Similarity	NPD4914	Approved
0.6494	Remote Similarity	NPD1549	Phase 2
0.6482	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD4361	Phase 2
0.6468	Remote Similarity	NPD7565	Approved
0.6468	Remote Similarity	NPD8285	Discontinued
0.645	Remote Similarity	NPD4915	Approved
0.645	Remote Similarity	NPD8461	Discontinued
0.6448	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7783	Phase 2
0.644	Remote Similarity	NPD5190	Phase 2
0.6439	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4363	Phase 3
0.6432	Remote Similarity	NPD4360	Phase 2
0.6422	Remote Similarity	NPD7435	Discontinued
0.642	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD3286	Discontinued
0.6411	Remote Similarity	NPD7301	Phase 3
0.6406	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD8059	Phase 3
0.6404	Remote Similarity	NPD8367	Approved
0.6402	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD8360	Approved
0.6396	Remote Similarity	NPD8361	Approved
0.6393	Remote Similarity	NPD6801	Discontinued
0.6393	Remote Similarity	NPD1934	Approved
0.6387	Remote Similarity	NPD4603	Phase 2
0.6387	Remote Similarity	NPD5844	Phase 1
0.6387	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD5544	Approved
0.6379	Remote Similarity	NPD2935	Discontinued
0.6379	Remote Similarity	NPD2796	Approved
0.6378	Remote Similarity	NPD3882	Suspended
0.6378	Remote Similarity	NPD7768	Phase 2
0.6373	Remote Similarity	NPD6559	Discontinued
0.6373	Remote Similarity	NPD4386	Approved
0.6373	Remote Similarity	NPD4387	Approved
0.6368	Remote Similarity	NPD8485	Approved
0.6364	Remote Similarity	NPD6746	Phase 2
0.6364	Remote Similarity	NPD5494	Approved
0.6345	Remote Similarity	NPD6835	Approved
0.6344	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD3818	Discontinued
0.6321	Remote Similarity	NPD3823	Discontinued
0.6319	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6166	Phase 2
0.6313	Remote Similarity	NPD8435	Approved
0.6313	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD8313	Approved
0.6308	Remote Similarity	NPD8312	Approved
0.6293	Remote Similarity	NPD8492	Approved
0.6292	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD8404	Phase 2
0.6289	Remote Similarity	NPD8368	Discontinued
0.6287	Remote Similarity	NPD4388	Approved
0.6284	Remote Similarity	NPD6599	Discontinued
0.6281	Remote Similarity	NPD7283	Approved
0.6276	Remote Similarity	NPD8407	Phase 2
0.6275	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD2654	Approved
0.627	Remote Similarity	NPD2801	Approved
0.627	Remote Similarity	NPD7972	Discontinued
0.6269	Remote Similarity	NPD7074	Phase 3
0.6269	Remote Similarity	NPD1729	Discontinued
0.625	Remote Similarity	NPD7177	Discontinued
0.625	Remote Similarity	NPD7978	Discontinued
0.625	Remote Similarity	NPD2346	Discontinued
0.625	Remote Similarity	NPD7907	Approved
0.625	Remote Similarity	NPD1164	Approved
0.6237	Remote Similarity	NPD5953	Discontinued
0.6236	Remote Similarity	NPD3750	Approved
0.6236	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD6874	Approved
0.6221	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7300	Phase 3
0.622	Remote Similarity	NPD7302	Phase 3
0.622	Remote Similarity	NPD7585	Approved
0.6218	Remote Similarity	NPD7054	Approved
0.6212	Remote Similarity	NPD8434	Phase 2
0.6205	Remote Similarity	NPD5637	Discontinued
0.6205	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD4750	Phase 3
0.6199	Remote Similarity	NPD3136	Phase 2
0.6197	Remote Similarity	NPD7930	Approved
0.6193	Remote Similarity	NPD6100	Approved
0.6193	Remote Similarity	NPD6099	Approved
0.6186	Remote Similarity	NPD7472	Approved
0.6182	Remote Similarity	NPD2932	Approved
0.6181	Remote Similarity	NPD1898	Discontinued
0.618	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4975	Approved
0.6176	Remote Similarity	NPD4974	Approved
0.6173	Remote Similarity	NPD7808	Phase 3

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