NPASS Compound

Structure

CID101207 OpenBabel06191715442D 45 47 0 0 1 0 0 0 0 0999 V2000 -2.9397 2.6696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2818 4.8324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3100 3.4924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0590 2.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0170 1.5613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2934 4.2301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7213 5.4788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9533 5.2583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7954 1.3776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9483 1.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0823 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0908 3.6213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8070 0.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9483 2.5391 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6730 4.0391 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3862 3.1097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8070 1.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8014 0.9410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 3.6213 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5908 4.4873 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5706 4.3344 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5706 0.1529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 0.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 1.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5908 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7954 3.1097 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1614 4.3344 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5391 2.5391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6730 2.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0823 4.0391 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 4.4873 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6685 1.3631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1614 0.1529 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 -0.9533 -0.7710 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7193 3.4924 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5441 5.2583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5305 2.6696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6730 3.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6910 4.8324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1305 5.4788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6643 2.3631 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5441 -0.7710 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 19 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 15 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 17 2 0 0 0 0 14 18 2 0 0 0 0 14 23 1 0 0 0 0 15 1 1 6 0 0 0 15 28 1 0 0 0 0 16 2 1 1 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 31 1 0 0 0 0 19 27 2 0 0 0 0 19 34 1 0 0 0 0 20 6 1 1 0 0 0 20 28 1 0 0 0 0 20 32 1 0 0 0 0 21 7 1 6 0 0 0 21 29 1 0 0 0 0 21 33 1 0 0 0 0 22 8 1 1 0 0 0 22 32 1 0 0 0 0 22 33 1 0 0 0 0 23 25 2 0 0 0 0 23 35 1 0 0 0 0 24 36 2 3 0 0 0 24 37 1 0 0 0 0 25 26 1 0 0 0 0 25 34 1 0 0 0 0 26 30 1 0 0 0 0 26 31 2 0 0 0 0 27 35 1 0 0 0 0 27 36 1 0 0 0 0 28 38 1 6 0 0 0 29 39 1 1 0 0 0 30 40 2 0 0 0 0 31 41 1 0 0 0 0 32 42 1 1 0 0 0 33 43 1 6 0 0 0 34 44 2 0 0 0 0 35 45 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	623.31
Volume:	649.354
LogP:	4.33
LogD:	2.422
LogS:	-3.29
# Rotatable Bonds:	0
TPSA:	188.11
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.217
Synthetic Accessibility Score:	6.812
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:	-5.961
MDCK Permeability:	3.6300107240094803e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.22
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.068

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	92.97112274169922%
Volume Distribution (VD):	0.69
Pgp-substrate:	8.750234603881836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.382
CYP1A2-substrate:	0.562
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.7
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.147
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.133
CYP3A4-substrate:	0.262

ADMET: Excretion

Clearance (CL):	1.892
Half-life (T1/2):	0.792

ADMET: Toxicity

hERG Blockers:	0.176
Human Hepatotoxicity (H-HT):	0.72
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.378
Rat Oral Acute Toxicity:	0.362
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.945
Carcinogencity:	0.203
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.889

Download Data

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

Natural Product: NPC101207

Natural Product ID:	NPC101207
*Common Name:**	Chaxamycin B
IUPAC Name:	n.a.
Synonyms:	Chaxamycin B
Standard InCHIKey:	YIELQFCSZNNHLS-AIGVRGBASA-N
Standard InCHI:	InChI=1S/C35H45NO9/c1-15-11-9-10-12-24(37)36-27-19(5)34(44)25-23(35(27)45)14-18(4)31(41)26(25)30(40)17(3)13-16(2)29(39)21(7)33(43)22(8)32(42)20(6)28(15)38/h9-16,20-22,28-29,32-33,38-39,41-43H,1-8H3,(H,36,37)/b11-9+,12-10-,17-13+/t15-,16-,20+,21+,22+,28-,29-,32+,33+/m0/s1
SMILES:	OC1=NC2=C(C)C(=O)c3c(C2=O)cc(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:	CHEMBL1814385
PubChem CID:	53344651
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	=	45.0	%	PMID[501725]

☑ 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 NPC101207 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	255
0.1-0.2	1098
0.2-0.3	3370
0.3-0.4	10033
0.4-0.5	9121
0.5-0.6	10867
0.6-0.7	7116
0.7-0.8	825
0.8-0.85	4
0.85-0.9	3
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9554	High Similarity	NPC54661
0.9554	High Similarity	NPC163924
0.9427	High Similarity	NPC314693
0.9308	High Similarity	NPC12890
0.8909	High Similarity	NPC313708
0.8902	High Similarity	NPC315406
0.8122	Intermediate Similarity	NPC313453
0.7962	Intermediate Similarity	NPC238108
0.7898	Intermediate Similarity	NPC86524
0.7898	Intermediate Similarity	NPC315275
0.7862	Intermediate Similarity	NPC162939
0.7826	Intermediate Similarity	NPC135524
0.7826	Intermediate Similarity	NPC193555
0.7764	Intermediate Similarity	NPC204045
0.7764	Intermediate Similarity	NPC305845
0.7756	Intermediate Similarity	NPC110609
0.7756	Intermediate Similarity	NPC246693
0.7756	Intermediate Similarity	NPC242358
0.7744	Intermediate Similarity	NPC314437
0.7736	Intermediate Similarity	NPC471452
0.7722	Intermediate Similarity	NPC236795
0.7716	Intermediate Similarity	NPC474961
0.7707	Intermediate Similarity	NPC115458
0.7702	Intermediate Similarity	NPC169452
0.7702	Intermediate Similarity	NPC181560
0.7692	Intermediate Similarity	NPC17083
0.7688	Intermediate Similarity	NPC13715
0.7647	Intermediate Similarity	NPC474861
0.7643	Intermediate Similarity	NPC58685
0.764	Intermediate Similarity	NPC242994
0.764	Intermediate Similarity	NPC138099
0.7636	Intermediate Similarity	NPC136878
0.7636	Intermediate Similarity	NPC143685
0.7625	Intermediate Similarity	NPC475957
0.7622	Intermediate Similarity	NPC244691
0.7622	Intermediate Similarity	NPC471906
0.761	Intermediate Similarity	NPC283088
0.7607	Intermediate Similarity	NPC73061
0.7607	Intermediate Similarity	NPC469520
0.7595	Intermediate Similarity	NPC53896
0.7595	Intermediate Similarity	NPC254603
0.7595	Intermediate Similarity	NPC52407
0.7593	Intermediate Similarity	NPC315578
0.7578	Intermediate Similarity	NPC87723
0.7578	Intermediate Similarity	NPC4214
0.7576	Intermediate Similarity	NPC34482
0.7562	Intermediate Similarity	NPC272268
0.756	Intermediate Similarity	NPC315520
0.7547	Intermediate Similarity	NPC50924
0.7547	Intermediate Similarity	NPC166480
0.7547	Intermediate Similarity	NPC474519
0.7547	Intermediate Similarity	NPC282780
0.7532	Intermediate Similarity	NPC70622
0.7531	Intermediate Similarity	NPC190457
0.7531	Intermediate Similarity	NPC26924
0.753	Intermediate Similarity	NPC85393
0.753	Intermediate Similarity	NPC271944
0.753	Intermediate Similarity	NPC110882
0.753	Intermediate Similarity	NPC470570
0.7529	Intermediate Similarity	NPC474824
0.7529	Intermediate Similarity	NPC182921
0.7529	Intermediate Similarity	NPC470408
0.7529	Intermediate Similarity	NPC218870
0.7516	Intermediate Similarity	NPC305060
0.7516	Intermediate Similarity	NPC53001
0.7516	Intermediate Similarity	NPC53414
0.7516	Intermediate Similarity	NPC31799
0.7516	Intermediate Similarity	NPC53206
0.7516	Intermediate Similarity	NPC471905
0.7515	Intermediate Similarity	NPC469854
0.7515	Intermediate Similarity	NPC21599
0.7515	Intermediate Similarity	NPC469856
0.7515	Intermediate Similarity	NPC48762
0.7515	Intermediate Similarity	NPC193703
0.7515	Intermediate Similarity	NPC29932
0.7515	Intermediate Similarity	NPC79627
0.75	Intermediate Similarity	NPC471971
0.75	Intermediate Similarity	NPC85310
0.75	Intermediate Similarity	NPC469855
0.75	Intermediate Similarity	NPC30846
0.75	Intermediate Similarity	NPC290803
0.75	Intermediate Similarity	NPC471972
0.75	Intermediate Similarity	NPC239136
0.75	Intermediate Similarity	NPC19631
0.75	Intermediate Similarity	NPC80035
0.75	Intermediate Similarity	NPC477221
0.7484	Intermediate Similarity	NPC231774
0.7484	Intermediate Similarity	NPC15837
0.7484	Intermediate Similarity	NPC3224
0.7484	Intermediate Similarity	NPC314048
0.747	Intermediate Similarity	NPC170055
0.747	Intermediate Similarity	NPC474630
0.7468	Intermediate Similarity	NPC41847
0.7468	Intermediate Similarity	NPC93015
0.7455	Intermediate Similarity	NPC66593
0.7453	Intermediate Similarity	NPC191976
0.7453	Intermediate Similarity	NPC254847
0.7453	Intermediate Similarity	NPC474311
0.7452	Intermediate Similarity	NPC99731
0.7451	Intermediate Similarity	NPC307174
0.7451	Intermediate Similarity	NPC282577
0.7446	Intermediate Similarity	NPC70340
0.7442	Intermediate Similarity	NPC313299
0.7439	Intermediate Similarity	NPC471444
0.7439	Intermediate Similarity	NPC187843
0.7438	Intermediate Similarity	NPC270899
0.7438	Intermediate Similarity	NPC202225
0.7438	Intermediate Similarity	NPC474394
0.7427	Intermediate Similarity	NPC4331
0.7427	Intermediate Similarity	NPC472211
0.7427	Intermediate Similarity	NPC96160
0.7425	Intermediate Similarity	NPC120536
0.7425	Intermediate Similarity	NPC285122
0.7425	Intermediate Similarity	NPC471970
0.7423	Intermediate Similarity	NPC295339
0.7421	Intermediate Similarity	NPC309430
0.7412	Intermediate Similarity	NPC470569
0.741	Intermediate Similarity	NPC218866
0.741	Intermediate Similarity	NPC300684
0.741	Intermediate Similarity	NPC48130
0.741	Intermediate Similarity	NPC84568
0.7405	Intermediate Similarity	NPC136588
0.7405	Intermediate Similarity	NPC199253
0.7394	Intermediate Similarity	NPC291078
0.7394	Intermediate Similarity	NPC248068
0.7394	Intermediate Similarity	NPC137649
0.7391	Intermediate Similarity	NPC249272
0.7389	Intermediate Similarity	NPC96024
0.7389	Intermediate Similarity	NPC282923
0.7378	Intermediate Similarity	NPC327916
0.7378	Intermediate Similarity	NPC42262
0.7378	Intermediate Similarity	NPC37992
0.7378	Intermediate Similarity	NPC241349
0.7378	Intermediate Similarity	NPC147542
0.7378	Intermediate Similarity	NPC471853
0.7378	Intermediate Similarity	NPC220496
0.7378	Intermediate Similarity	NPC32749
0.7375	Intermediate Similarity	NPC139074
0.7375	Intermediate Similarity	NPC477139
0.7375	Intermediate Similarity	NPC37299
0.7375	Intermediate Similarity	NPC213485
0.7375	Intermediate Similarity	NPC78307
0.7375	Intermediate Similarity	NPC40524
0.7375	Intermediate Similarity	NPC180261
0.7375	Intermediate Similarity	NPC48036
0.7375	Intermediate Similarity	NPC114183
0.7372	Intermediate Similarity	NPC306765
0.7365	Intermediate Similarity	NPC478019
0.7362	Intermediate Similarity	NPC177307
0.7362	Intermediate Similarity	NPC475974
0.7362	Intermediate Similarity	NPC9121
0.7362	Intermediate Similarity	NPC416
0.7362	Intermediate Similarity	NPC61590
0.7362	Intermediate Similarity	NPC173980
0.7362	Intermediate Similarity	NPC472403
0.7362	Intermediate Similarity	NPC61398
0.7358	Intermediate Similarity	NPC475042
0.7358	Intermediate Similarity	NPC471851
0.7358	Intermediate Similarity	NPC476847
0.7358	Intermediate Similarity	NPC244699
0.7356	Intermediate Similarity	NPC326084
0.7355	Intermediate Similarity	NPC199273
0.7355	Intermediate Similarity	NPC68756
0.7355	Intermediate Similarity	NPC234890
0.7355	Intermediate Similarity	NPC152525
0.7355	Intermediate Similarity	NPC74507
0.7353	Intermediate Similarity	NPC255641
0.7353	Intermediate Similarity	NPC477914
0.7353	Intermediate Similarity	NPC290954
0.7353	Intermediate Similarity	NPC470568
0.7349	Intermediate Similarity	NPC471682
0.7346	Intermediate Similarity	NPC322526
0.7346	Intermediate Similarity	NPC118919
0.7342	Intermediate Similarity	NPC278928
0.7342	Intermediate Similarity	NPC146647
0.7342	Intermediate Similarity	NPC474546
0.7342	Intermediate Similarity	NPC25736
0.7342	Intermediate Similarity	NPC34414
0.7341	Intermediate Similarity	NPC478027
0.7337	Intermediate Similarity	NPC329790
0.7337	Intermediate Similarity	NPC94781
0.7337	Intermediate Similarity	NPC112816
0.7333	Intermediate Similarity	NPC290550
0.7333	Intermediate Similarity	NPC246638
0.7333	Intermediate Similarity	NPC91019
0.7333	Intermediate Similarity	NPC106519
0.7333	Intermediate Similarity	NPC257003
0.7329	Intermediate Similarity	NPC44437
0.7329	Intermediate Similarity	NPC288089
0.7329	Intermediate Similarity	NPC12070
0.7326	Intermediate Similarity	NPC155686
0.7326	Intermediate Similarity	NPC208806
0.7325	Intermediate Similarity	NPC72667
0.7317	Intermediate Similarity	NPC306835
0.7317	Intermediate Similarity	NPC471602
0.7317	Intermediate Similarity	NPC256463
0.7317	Intermediate Similarity	NPC216312
0.7317	Intermediate Similarity	NPC143438
0.7317	Intermediate Similarity	NPC114620
0.7317	Intermediate Similarity	NPC476477

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 NPC101207 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	673
0.2-0.3	1095
0.3-0.4	2300
0.4-0.5	2978
0.5-0.6	1577
0.6-0.7	319
0.7-0.8	25
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
0.7453	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD8150	Discontinued
0.7308	Intermediate Similarity	NPD5035	Approved
0.7253	Intermediate Similarity	NPD5028	Approved
0.7253	Intermediate Similarity	NPD4955	Approved
0.7253	Intermediate Similarity	NPD4954	Approved
0.7253	Intermediate Similarity	NPD36	Approved
0.7253	Intermediate Similarity	NPD5026	Approved
0.7253	Intermediate Similarity	NPD5034	Approved
0.7229	Intermediate Similarity	NPD3400	Discontinued
0.7198	Intermediate Similarity	NPD5030	Phase 2
0.7197	Intermediate Similarity	NPD1470	Approved
0.7189	Intermediate Similarity	NPD5037	Approved
0.7189	Intermediate Similarity	NPD5038	Approved
0.7143	Intermediate Similarity	NPD3300	Phase 2
0.7135	Intermediate Similarity	NPD5036	Approved
0.7101	Intermediate Similarity	NPD7390	Discontinued
0.7091	Intermediate Similarity	NPD5405	Approved
0.7091	Intermediate Similarity	NPD5404	Approved
0.7091	Intermediate Similarity	NPD5408	Approved
0.7091	Intermediate Similarity	NPD5406	Approved
0.7088	Intermediate Similarity	NPD4956	Approved
0.7059	Intermediate Similarity	NPD8366	Approved
0.7059	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD8469	Approved
0.7035	Intermediate Similarity	NPD7801	Approved
0.703	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD8151	Discontinued
0.7011	Intermediate Similarity	NPD5039	Approved
0.7	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6212	Phase 3
0.7	Intermediate Similarity	NPD6213	Phase 3
0.6993	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD5032	Approved
0.6947	Remote Similarity	NPD5968	Phase 3
0.6943	Remote Similarity	NPD7700	Phase 2
0.6943	Remote Similarity	NPD7699	Phase 2
0.6943	Remote Similarity	NPD1201	Approved
0.6932	Remote Similarity	NPD7819	Suspended
0.6923	Remote Similarity	NPD7473	Discontinued
0.6923	Remote Similarity	NPD8491	Approved
0.6919	Remote Similarity	NPD5029	Approved
0.6919	Remote Similarity	NPD5027	Approved
0.6919	Remote Similarity	NPD5031	Approved
0.6904	Remote Similarity	NPD8320	Phase 1
0.6904	Remote Similarity	NPD8319	Approved
0.69	Remote Similarity	NPD7874	Approved
0.69	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3226	Approved
0.6885	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6535	Approved
0.6875	Remote Similarity	NPD6534	Approved
0.6872	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2533	Approved
0.686	Remote Similarity	NPD2534	Approved
0.686	Remote Similarity	NPD2532	Approved
0.6842	Remote Similarity	NPD6836	Approved
0.6831	Remote Similarity	NPD5033	Approved
0.6788	Remote Similarity	NPD943	Approved
0.6768	Remote Similarity	NPD7698	Approved
0.6768	Remote Similarity	NPD7696	Phase 3
0.6768	Remote Similarity	NPD7697	Approved
0.6758	Remote Similarity	NPD5711	Approved
0.6758	Remote Similarity	NPD6232	Discontinued
0.6758	Remote Similarity	NPD5710	Approved
0.6757	Remote Similarity	NPD6020	Phase 2
0.6734	Remote Similarity	NPD7871	Phase 2
0.6734	Remote Similarity	NPD7870	Phase 2
0.6726	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD7282	Approved
0.6717	Remote Similarity	NPD6823	Phase 2
0.6716	Remote Similarity	NPD7701	Phase 2
0.6714	Remote Similarity	NPD8067	Phase 3
0.6703	Remote Similarity	NPD6959	Discontinued
0.6702	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6777	Approved
0.6701	Remote Similarity	NPD6781	Approved
0.6701	Remote Similarity	NPD6779	Approved
0.6701	Remote Similarity	NPD6780	Approved
0.6701	Remote Similarity	NPD6778	Approved
0.6701	Remote Similarity	NPD6782	Approved
0.6701	Remote Similarity	NPD6776	Approved
0.6701	Remote Similarity	NPD4914	Approved
0.6684	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4380	Phase 2
0.665	Remote Similarity	NPD7565	Approved
0.665	Remote Similarity	NPD8285	Discontinued
0.6646	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD3286	Discontinued
0.6608	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6651	Approved
0.6607	Remote Similarity	NPD1607	Approved
0.6596	Remote Similarity	NPD3823	Discontinued
0.659	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD2935	Discontinued
0.6585	Remote Similarity	NPD7301	Phase 3
0.658	Remote Similarity	NPD8361	Approved
0.658	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.658	Remote Similarity	NPD8360	Approved
0.6579	Remote Similarity	NPD8312	Approved
0.6579	Remote Similarity	NPD8313	Approved
0.6566	Remote Similarity	NPD5544	Approved
0.6561	Remote Similarity	NPD6104	Discontinued
0.6556	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7972	Discontinued
0.655	Remote Similarity	NPD4387	Approved
0.655	Remote Similarity	NPD4386	Approved
0.655	Remote Similarity	NPD7978	Discontinued
0.655	Remote Similarity	NPD2346	Discontinued
0.6548	Remote Similarity	NPD8485	Approved
0.6548	Remote Similarity	NPD4915	Approved
0.6543	Remote Similarity	NPD5190	Phase 2
0.6538	Remote Similarity	NPD7075	Discontinued
0.6536	Remote Similarity	NPD7411	Suspended
0.6535	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD1510	Phase 2
0.6528	Remote Similarity	NPD6835	Approved
0.6527	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7177	Discontinued
0.6517	Remote Similarity	NPD7435	Discontinued
0.6506	Remote Similarity	NPD3136	Phase 2
0.6505	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD7584	Approved
0.6502	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2932	Approved
0.6495	Remote Similarity	NPD8435	Approved
0.6495	Remote Similarity	NPD8059	Phase 3
0.6495	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4603	Phase 2
0.6488	Remote Similarity	NPD1240	Approved
0.6477	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD5637	Discontinued
0.6474	Remote Similarity	NPD8368	Discontinued
0.6465	Remote Similarity	NPD4388	Approved
0.6465	Remote Similarity	NPD7654	Discontinued
0.6463	Remote Similarity	NPD1164	Approved
0.6462	Remote Similarity	NPD7283	Approved
0.6459	Remote Similarity	NPD8404	Phase 2
0.6458	Remote Similarity	NPD8407	Phase 2
0.6456	Remote Similarity	NPD7783	Phase 2
0.6456	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.645	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD2799	Discontinued
0.6416	Remote Similarity	NPD1549	Phase 2
0.6409	Remote Similarity	NPD6844	Discontinued
0.64	Remote Similarity	NPD6874	Approved
0.6398	Remote Similarity	NPD3019	Approved
0.6392	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD8434	Phase 2
0.639	Remote Similarity	NPD7300	Phase 3
0.639	Remote Similarity	NPD7302	Phase 3
0.6387	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD2800	Approved
0.6374	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD2344	Approved
0.6352	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.635	Remote Similarity	NPD4974	Approved
0.635	Remote Similarity	NPD4975	Approved
0.6343	Remote Similarity	NPD8166	Discontinued
0.6343	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD4628	Phase 3
0.6341	Remote Similarity	NPD1755	Approved
0.6339	Remote Similarity	NPD7318	Phase 3
0.6333	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7458	Discontinued
0.6332	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD4361	Phase 2
0.6332	Remote Similarity	NPD4931	Phase 2
0.633	Remote Similarity	NPD6894	Phase 1
0.6321	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.632	Remote Similarity	NPD8461	Discontinued
0.6319	Remote Similarity	NPD1934	Approved
0.6319	Remote Similarity	NPD6801	Discontinued
0.6318	Remote Similarity	NPD5608	Approved
0.6318	Remote Similarity	NPD5609	Approved
0.6316	Remote Similarity	NPD5844	Phase 1
0.6316	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.631	Remote Similarity	NPD7315	Approved
0.6304	Remote Similarity	NPD7768	Phase 2
0.6304	Remote Similarity	NPD3882	Suspended
0.6302	Remote Similarity	NPD6559	Discontinued
0.6301	Remote Similarity	NPD2796	Approved
0.6301	Remote Similarity	NPD9570	Approved
0.63	Remote Similarity	NPD5543	Approved
0.6293	Remote Similarity	NPD6807	Phase 3
0.629	Remote Similarity	NPD5494	Approved
0.629	Remote Similarity	NPD6746	Phase 2
0.6287	Remote Similarity	NPD4208	Discontinued
0.6286	Remote Similarity	NPD7930	Approved
0.6281	Remote Similarity	NPD4363	Phase 3
0.6281	Remote Similarity	NPD4360	Phase 2
0.6279	Remote Similarity	NPD3553	Approved
0.6279	Remote Similarity	NPD3554	Approved
0.6279	Remote Similarity	NPD3555	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