NPASS Compound

Structure

NPC471048 OpenBabel07101719512D 72 75 0 0 1 0 0 0 0 0999 V2000 3.9053 -5.6875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8897 -9.0701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5089 -0.6833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8530 -5.6875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3174 -8.9210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5007 -6.1209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.6781 -6.7157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9053 -0.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3922 -4.8442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9526 -9.3351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0691 -1.5522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.1229 -1.4608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.7420 -2.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.1623 -1.6211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.4005 -3.1246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.8208 -2.5332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.0744 -6.3818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.4432 -8.0277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.0246 -6.1688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.3935 -7.8148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9836 -2.8771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.2991 -3.6717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.8831 -7.7372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.0984 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9314 -2.3140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3660 -4.8442 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.2545 -8.6561 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.4218 -5.8047 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 16.4399 -3.2849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.7836 -7.3113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.6842 -6.8853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6018 -2.3675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4082 -2.1350 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 14.2235 -7.0207 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 15.1379 -4.3572 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.9053 -2.3140 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 14.1171 -3.9205 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.8530 -4.0008 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.4936 -7.7120 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.2615 -4.8442 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.4936 -1.9763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4082 -7.5533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3922 -3.1574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8268 -4.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4218 -3.8836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.2235 -2.6676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.1379 -5.3311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6018 -7.3208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8853 -3.0271 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 12.4641 -1.8959 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.3660 -3.1574 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 12.4641 -7.7924 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.3138 -4.8442 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 14.8216 -6.2522 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 14.8216 -3.4361 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 19.6345 -6.6724 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 14.2661 -4.8829 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2545 -1.0323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.7994 -8.4452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9053 -4.0008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3138 -3.1574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5007 -3.5674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.8831 -1.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.0984 -5.4914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0691 -8.1361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4706 -0.4967 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4967 -1.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4706 -2.4445 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3922 -1.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4445 -1.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8853 -6.6612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4706 -1.4706 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 54 1 0 0 0 0 8 69 1 0 0 0 0 9 26 1 0 0 0 0 10 27 1 0 0 0 0 11 32 2 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 2 0 0 0 0 15 29 2 0 0 0 0 16 29 1 0 0 0 0 17 19 1 0 0 0 0 17 30 2 0 0 0 0 18 20 2 0 0 0 0 18 30 1 0 0 0 0 19 31 2 0 0 0 0 20 31 1 0 0 0 0 21 22 1 0 0 0 0 21 33 1 0 0 0 0 22 37 1 0 0 0 0 23 30 1 0 0 0 0 23 34 1 0 0 0 0 24 29 1 0 0 0 0 24 35 1 0 0 0 0 25 36 1 0 0 0 0 25 70 1 0 0 0 0 26 38 1 0 0 0 0 27 39 1 0 0 0 0 28 40 1 0 0 0 0 28 71 1 0 0 0 0 31 56 1 0 0 0 0 32 41 1 0 0 0 0 32 49 1 0 0 0 0 33 46 1 0 0 0 0 33 50 1 0 0 0 0 34 42 1 0 0 0 0 34 54 1 0 0 0 0 35 47 1 0 0 0 0 35 55 1 0 0 0 0 36 43 1 0 0 0 0 36 69 1 0 0 0 0 37 55 1 0 0 0 0 37 57 1 0 0 0 0 38 44 1 0 0 0 0 38 51 1 0 0 0 0 39 48 1 0 0 0 0 39 52 1 0 0 0 0 40 45 1 0 0 0 0 40 53 1 0 0 0 0 41 50 2 0 0 0 0 41 58 1 0 0 0 0 42 52 2 0 0 0 0 42 59 1 0 0 0 0 43 51 2 0 0 0 0 43 60 1 0 0 0 0 44 53 2 0 0 0 0 44 61 1 0 0 0 0 45 49 2 0 0 0 0 45 62 1 0 0 0 0 46 55 1 0 0 0 0 46 63 2 0 0 0 0 47 54 1 0 0 0 0 47 64 2 0 0 0 0 48 65 2 0 0 0 0 48 71 1 0 0 0 0 66 72 1 0 0 0 0 67 72 2 0 0 0 0 68 72 2 0 0 0 0 70 72 1 0 0 0 0 M CHG 1 56 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	1028.43
Volume:	999.803
LogP:	0.664
LogD:	0.693
LogS:	-1.365
# Rotatable Bonds:	18
TPSA:	332.03
# H-Bond Aceptor:	23
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	24

MedChem Properties

QED Drug-Likeness Score:	0.053
Synthetic Accessibility Score:	7.276
Fsp3:	0.542
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:	-6.415
MDCK Permeability:	1.149121999333147e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.474
20% Bioavailability (F20%):	0.427
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	69.70331573486328%
Volume Distribution (VD):	0.47
Pgp-substrate:	11.047356605529785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.061
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.084
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.02

ADMET: Excretion

Clearance (CL):	2.913
Half-life (T1/2):	0.452

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.956
Drug-inuced Liver Injury (DILI):	0.992
AMES Toxicity:	0.575
Rat Oral Acute Toxicity:	0.803
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.384
Carcinogencity:	0.749
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.829

Download Data

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

Natural Product: NPC471048

Natural Product ID:	NPC471048
*Common Name:**	Symplostatin 10
IUPAC Name:	sodium;[(2R)-3-[[(2S,3S)-1-[[(2S,5S,8S,11R,12S,15Z,18S,21R)-2-benzyl-8-[(2R)-butan-2-yl]-15-ethylidene-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-2-methoxy-3-oxopropyl] sulfate
Synonyms:	symplostatin 10
Standard InCHIKey:	LKYJXYOTVBTLMJ-SEWPLWSESA-M
Standard InCHI:	InChI=1S/C48H67N7O16S.Na/c1-9-26(4)38(51-43(60)36(69-8)25-70-72(66,67)68)44(61)53-40-28(6)71-48(65)39(27(5)10-2)52-42(59)34(23-30-17-19-31(56)20-18-30)54(7)47(64)35(24-29-15-13-12-14-16-29)55-37(57)22-21-33(46(55)63)50-41(58)32(11-3)49-45(40)62;/h11-20,26-28,33-40,56-57H,9-10,21-25H2,1-8H3,(H,49,62)(H,50,58)(H,51,60)(H,52,59)(H,53,61)(H,66,67,68);/q;+1/p-1/b32-11-;/t26-,27+,28+,33-,34-,35-,36+,37+,38-,39-,40-;/m0./s1
SMILES:	CC[C@@H]([C@@H](C(=N[C@H]1[C@@H](C)OC(=O)[C@@H](N=C(O)[C@H](Cc2ccc(cc2)[O-])N(C)C(=O)[C@@H](N2C(=O)[C@@H](N=C(/C(=C/C)/N=C1O)O)CC[C@H]2O)Cc1ccccc1)[C@@H](CC)C)O)N=C([C@@H](COS(=O)(=O)O)OC)O)C.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2338549
PubChem CID:	71717105
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
NPO33098	cyanobacteria	Phylum	n.a.	Bacteria	n.a.	n.a.	n.a.	PMID[19715320]
NPO33098	cyanobacteria	Phylum	n.a.	Bacteria	n.a.	n.a.	n.a.	PMID[23350733]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4
Others	1

Activity Type	# Activity
Individual Protein	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	IC50	=	21.0	nM	PMID[496120]
NPT2	Others	Unspecified		Activity	=	79.4	%	PMID[496120]
NPT2	Others	Unspecified		IC50	>	10000.0	nM	PMID[496120]
NPT2	Others	Unspecified		IC50	=	222.0	nM	PMID[496120]
NPT2	Others	Unspecified		IC50	=	44.0	nM	PMID[496120]

☑ 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 NPC471048 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	213
0.1-0.2	1040
0.2-0.3	4402
0.3-0.4	12763
0.4-0.5	14101
0.5-0.6	9084
0.6-0.7	753
0.7-0.8	279
0.8-0.85	27
0.85-0.9	20
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471049
1.0	High Similarity	NPC471050
0.9586	High Similarity	NPC163961
0.9586	High Similarity	NPC473305
0.9401	High Similarity	NPC476321
0.9345	High Similarity	NPC471526
0.9333	High Similarity	NPC279871
0.929	High Similarity	NPC294951
0.9167	High Similarity	NPC269750
0.9167	High Similarity	NPC194671
0.9102	High Similarity	NPC473354
0.908	High Similarity	NPC471051
0.908	High Similarity	NPC471053
0.908	High Similarity	NPC471052
0.9042	High Similarity	NPC273755
0.8971	High Similarity	NPC473407
0.8971	High Similarity	NPC473378
0.8935	High Similarity	NPC50016
0.8929	High Similarity	NPC137627
0.8929	High Similarity	NPC306804
0.8916	High Similarity	NPC107938
0.8916	High Similarity	NPC294516
0.8876	High Similarity	NPC159767
0.8876	High Similarity	NPC155506
0.8876	High Similarity	NPC26108
0.887	High Similarity	NPC302715
0.883	High Similarity	NPC45037
0.881	High Similarity	NPC40234
0.8765	High Similarity	NPC476227
0.8757	High Similarity	NPC230611
0.8655	High Similarity	NPC473402
0.8644	High Similarity	NPC102959
0.8596	High Similarity	NPC60516
0.8488	Intermediate Similarity	NPC248670
0.848	Intermediate Similarity	NPC475204
0.848	Intermediate Similarity	NPC475123
0.848	Intermediate Similarity	NPC46009
0.8352	Intermediate Similarity	NPC65714
0.8333	Intermediate Similarity	NPC471165
0.8287	Intermediate Similarity	NPC240130
0.8287	Intermediate Similarity	NPC61332
0.8284	Intermediate Similarity	NPC471527
0.8261	Intermediate Similarity	NPC473371
0.8246	Intermediate Similarity	NPC63931
0.8218	Intermediate Similarity	NPC89831
0.8216	Intermediate Similarity	NPC471592
0.8125	Intermediate Similarity	NPC158277
0.8101	Intermediate Similarity	NPC473404
0.8075	Intermediate Similarity	NPC323662
0.8057	Intermediate Similarity	NPC196091
0.7967	Intermediate Similarity	NPC315542
0.7957	Intermediate Similarity	NPC328763
0.7927	Intermediate Similarity	NPC220060
0.7914	Intermediate Similarity	NPC163392
0.7914	Intermediate Similarity	NPC239762
0.7895	Intermediate Similarity	NPC477551
0.7884	Intermediate Similarity	NPC477550
0.7884	Intermediate Similarity	NPC477552
0.788	Intermediate Similarity	NPC94862
0.787	Intermediate Similarity	NPC233702
0.7844	Intermediate Similarity	NPC16188
0.7824	Intermediate Similarity	NPC473341
0.7824	Intermediate Similarity	NPC262166
0.7821	Intermediate Similarity	NPC477462
0.7796	Intermediate Similarity	NPC174122
0.7796	Intermediate Similarity	NPC64140
0.7791	Intermediate Similarity	NPC127741
0.7784	Intermediate Similarity	NPC81026
0.7766	Intermediate Similarity	NPC469445
0.7753	Intermediate Similarity	NPC471568
0.7753	Intermediate Similarity	NPC473693
0.7742	Intermediate Similarity	NPC234069
0.774	Intermediate Similarity	NPC63040
0.774	Intermediate Similarity	NPC302597
0.7727	Intermediate Similarity	NPC22883
0.7727	Intermediate Similarity	NPC5719
0.7727	Intermediate Similarity	NPC472923
0.7727	Intermediate Similarity	NPC217804
0.7727	Intermediate Similarity	NPC210377
0.7725	Intermediate Similarity	NPC266741
0.7719	Intermediate Similarity	NPC202198
0.7719	Intermediate Similarity	NPC122590
0.7708	Intermediate Similarity	NPC469443
0.7706	Intermediate Similarity	NPC473491
0.7704	Intermediate Similarity	NPC469444
0.7697	Intermediate Similarity	NPC186617
0.7692	Intermediate Similarity	NPC475421
0.7688	Intermediate Similarity	NPC326027
0.7684	Intermediate Similarity	NPC15068
0.7684	Intermediate Similarity	NPC254700
0.7684	Intermediate Similarity	NPC61004
0.7683	Intermediate Similarity	NPC6570
0.7677	Intermediate Similarity	NPC326333
0.7674	Intermediate Similarity	NPC39431
0.766	Intermediate Similarity	NPC248822
0.7657	Intermediate Similarity	NPC469243
0.7654	Intermediate Similarity	NPC198254
0.7654	Intermediate Similarity	NPC274198
0.7633	Intermediate Similarity	NPC135121
0.763	Intermediate Similarity	NPC476268
0.7627	Intermediate Similarity	NPC223207
0.7619	Intermediate Similarity	NPC477217
0.7619	Intermediate Similarity	NPC201244
0.7614	Intermediate Similarity	NPC478005
0.76	Intermediate Similarity	NPC25539
0.7598	Intermediate Similarity	NPC280022
0.7588	Intermediate Similarity	NPC469442
0.7588	Intermediate Similarity	NPC277306
0.7584	Intermediate Similarity	NPC290755
0.7584	Intermediate Similarity	NPC471771
0.7584	Intermediate Similarity	NPC304074
0.7582	Intermediate Similarity	NPC196243
0.7581	Intermediate Similarity	NPC138083
0.7574	Intermediate Similarity	NPC262077
0.7568	Intermediate Similarity	NPC470903
0.7568	Intermediate Similarity	NPC470112
0.7568	Intermediate Similarity	NPC167763
0.7566	Intermediate Similarity	NPC477526
0.7557	Intermediate Similarity	NPC475544
0.7556	Intermediate Similarity	NPC276506
0.7554	Intermediate Similarity	NPC32064
0.7552	Intermediate Similarity	NPC144314
0.7545	Intermediate Similarity	NPC476989
0.7544	Intermediate Similarity	NPC2501
0.7543	Intermediate Similarity	NPC56635
0.7543	Intermediate Similarity	NPC197743
0.7543	Intermediate Similarity	NPC297145
0.7542	Intermediate Similarity	NPC209463
0.7542	Intermediate Similarity	NPC141957
0.754	Intermediate Similarity	NPC276120
0.7527	Intermediate Similarity	NPC136797
0.7527	Intermediate Similarity	NPC164608
0.7526	Intermediate Similarity	NPC242728
0.7514	Intermediate Similarity	NPC477637
0.7514	Intermediate Similarity	NPC328494
0.7513	Intermediate Similarity	NPC50548
0.75	Intermediate Similarity	NPC119652
0.75	Intermediate Similarity	NPC62104
0.75	Intermediate Similarity	NPC7817
0.75	Intermediate Similarity	NPC97526
0.75	Intermediate Similarity	NPC1390
0.75	Intermediate Similarity	NPC149962
0.75	Intermediate Similarity	NPC244336
0.75	Intermediate Similarity	NPC4910
0.75	Intermediate Similarity	NPC91953
0.75	Intermediate Similarity	NPC475168
0.7487	Intermediate Similarity	NPC299806
0.7463	Intermediate Similarity	NPC478007
0.7456	Intermediate Similarity	NPC52748
0.7448	Intermediate Similarity	NPC184933
0.7448	Intermediate Similarity	NPC59827
0.7444	Intermediate Similarity	NPC328649
0.7444	Intermediate Similarity	NPC473502
0.744	Intermediate Similarity	NPC197921
0.7439	Intermediate Similarity	NPC257390
0.7429	Intermediate Similarity	NPC473580
0.7416	Intermediate Similarity	NPC241794
0.7414	Intermediate Similarity	NPC5194
0.7414	Intermediate Similarity	NPC261934
0.7407	Intermediate Similarity	NPC329731
0.7401	Intermediate Similarity	NPC319320
0.7401	Intermediate Similarity	NPC287757
0.7396	Intermediate Similarity	NPC161069
0.7396	Intermediate Similarity	NPC469360
0.7396	Intermediate Similarity	NPC314083
0.7391	Intermediate Similarity	NPC478008
0.7387	Intermediate Similarity	NPC219350
0.7387	Intermediate Similarity	NPC194699
0.7385	Intermediate Similarity	NPC123859
0.7384	Intermediate Similarity	NPC9373
0.7384	Intermediate Similarity	NPC471820
0.7384	Intermediate Similarity	NPC471821
0.7381	Intermediate Similarity	NPC307357
0.7381	Intermediate Similarity	NPC46098
0.7381	Intermediate Similarity	NPC268841
0.7374	Intermediate Similarity	NPC191863
0.7374	Intermediate Similarity	NPC133470
0.7374	Intermediate Similarity	NPC289776
0.7371	Intermediate Similarity	NPC470902
0.7366	Intermediate Similarity	NPC153554
0.7365	Intermediate Similarity	NPC68865
0.736	Intermediate Similarity	NPC311357
0.7358	Intermediate Similarity	NPC477632
0.7358	Intermediate Similarity	NPC477638
0.7356	Intermediate Similarity	NPC162104
0.7347	Intermediate Similarity	NPC473450
0.7333	Intermediate Similarity	NPC45191
0.7333	Intermediate Similarity	NPC477527
0.733	Intermediate Similarity	NPC29531
0.733	Intermediate Similarity	NPC244509
0.7314	Intermediate Similarity	NPC56685
0.731	Intermediate Similarity	NPC209509
0.7283	Intermediate Similarity	NPC475532
0.7267	Intermediate Similarity	NPC314358
0.7251	Intermediate Similarity	NPC476978
0.7243	Intermediate Similarity	NPC165285
0.7243	Intermediate Similarity	NPC17698
0.7225	Intermediate Similarity	NPC145113
0.7225	Intermediate Similarity	NPC138775
0.7219	Intermediate Similarity	NPC313694

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 NPC471048 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	128
0.1-0.2	414
0.2-0.3	776
0.3-0.4	1844
0.4-0.5	3084
0.5-0.6	2538
0.6-0.7	359
0.7-0.8	7
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
0.7753	Intermediate Similarity	NPD7608	Discontinued
0.7644	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7131	Phase 3
0.7296	Intermediate Similarity	NPD7811	Phase 3
0.7296	Intermediate Similarity	NPD7810	Phase 3
0.7225	Intermediate Similarity	NPD8323	Discontinued
0.7211	Intermediate Similarity	NPD6851	Approved
0.7211	Intermediate Similarity	NPD6853	Approved
0.7211	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8019	Approved
0.7198	Intermediate Similarity	NPD8303	Discontinued
0.712	Intermediate Similarity	NPD7484	Phase 3
0.712	Intermediate Similarity	NPD7485	Phase 3
0.7111	Intermediate Similarity	NPD7495	Discontinued
0.7105	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD8417	Discontinued
0.7035	Intermediate Similarity	NPD7565	Approved
0.7011	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6297	Approved
0.6994	Remote Similarity	NPD7978	Discontinued
0.6981	Remote Similarity	NPD8356	Approved
0.6964	Remote Similarity	NPD3136	Phase 2
0.6959	Remote Similarity	NPD8172	Phase 2
0.6959	Remote Similarity	NPD8173	Phase 2
0.6957	Remote Similarity	NPD8031	Discontinued
0.6936	Remote Similarity	NPD7450	Phase 2
0.6882	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7303	Discontinued
0.6867	Remote Similarity	NPD3125	Approved
0.6852	Remote Similarity	NPD8430	Approved
0.6805	Remote Similarity	NPD5203	Approved
0.6805	Remote Similarity	NPD4620	Approved
0.6805	Remote Similarity	NPD5201	Approved
0.6805	Remote Similarity	NPD4617	Approved
0.6805	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7613	Discontinued
0.6776	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5137	Approved
0.6761	Remote Similarity	NPD6681	Discovery
0.6761	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD2017	Approved
0.6755	Remote Similarity	NPD2890	Approved
0.6755	Remote Similarity	NPD2889	Approved
0.6755	Remote Similarity	NPD2888	Approved
0.6751	Remote Similarity	NPD8025	Phase 2
0.6744	Remote Similarity	NPD6346	Approved
0.6744	Remote Similarity	NPD5119	Approved
0.6744	Remote Similarity	NPD5120	Approved
0.6744	Remote Similarity	NPD5121	Approved
0.674	Remote Similarity	NPD7523	Phase 3
0.6716	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4659	Approved
0.6703	Remote Similarity	NPD7972	Discontinued
0.6686	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5745	Approved
0.6685	Remote Similarity	NPD5481	Discontinued
0.6685	Remote Similarity	NPD6390	Discontinued
0.6685	Remote Similarity	NPD3400	Discontinued
0.6684	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2098	Approved
0.6684	Remote Similarity	NPD5218	Approved
0.6684	Remote Similarity	NPD5219	Approved
0.6667	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2097	Approved
0.6649	Remote Similarity	NPD5445	Approved
0.6648	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2584	Suspended
0.6633	Remote Similarity	NPD7281	Phase 3
0.6633	Remote Similarity	NPD7617	Discontinued
0.6633	Remote Similarity	NPD7280	Phase 3
0.6632	Remote Similarity	NPD4652	Approved
0.6629	Remote Similarity	NPD6852	Discontinued
0.6629	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4619	Approved
0.6628	Remote Similarity	NPD4621	Approved
0.6628	Remote Similarity	NPD1330	Phase 2
0.6612	Remote Similarity	NPD8315	Phase 1
0.6611	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5485	Approved
0.6598	Remote Similarity	NPD5484	Approved
0.6592	Remote Similarity	NPD6676	Phase 2
0.6578	Remote Similarity	NPD5967	Approved
0.6578	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6073	Approved
0.657	Remote Similarity	NPD5746	Approved
0.6564	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5355	Approved
0.6559	Remote Similarity	NPD5356	Approved
0.6559	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7583	Approved
0.6546	Remote Similarity	NPD5313	Approved
0.6546	Remote Similarity	NPD5312	Approved
0.6534	Remote Similarity	NPD6295	Approved
0.6534	Remote Similarity	NPD6294	Approved
0.6531	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD4103	Phase 2
0.6529	Remote Similarity	NPD2159	Approved
0.6529	Remote Similarity	NPD2160	Approved
0.6529	Remote Similarity	NPD2625	Approved
0.6529	Remote Similarity	NPD2627	Approved
0.6529	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD2628	Approved
0.6529	Remote Similarity	NPD2626	Approved
0.6526	Remote Similarity	NPD5823	Approved
0.6524	Remote Similarity	NPD7585	Approved
0.6522	Remote Similarity	NPD6863	Phase 2
0.6514	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD3878	Approved
0.6508	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD8161	Suspended
0.6505	Remote Similarity	NPD7110	Phase 1
0.6505	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3455	Phase 2
0.6484	Remote Similarity	NPD6088	Approved
0.648	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD3879	Approved
0.6474	Remote Similarity	NPD4738	Phase 2
0.6474	Remote Similarity	NPD6862	Phase 2
0.6467	Remote Similarity	NPD5723	Approved
0.6464	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD3965	Phase 1
0.6461	Remote Similarity	NPD2240	Approved
0.6461	Remote Similarity	NPD4173	Approved
0.6461	Remote Similarity	NPD4172	Approved
0.6461	Remote Similarity	NPD2239	Approved
0.6457	Remote Similarity	NPD8265	Approved
0.6457	Remote Similarity	NPD5296	Approved
0.6457	Remote Similarity	NPD8416	Discontinued
0.6453	Remote Similarity	NPD4177	Approved
0.6453	Remote Similarity	NPD4175	Approved
0.6448	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD3536	Discontinued
0.6447	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD8162	Phase 2
0.644	Remote Similarity	NPD2904	Discontinued
0.6436	Remote Similarity	NPD6504	Approved
0.6436	Remote Similarity	NPD5772	Approved
0.6436	Remote Similarity	NPD5773	Approved
0.6436	Remote Similarity	NPD6505	Approved
0.6436	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD6253	Approved
0.6422	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6312	Discontinued
0.6421	Remote Similarity	NPD8070	Approved
0.642	Remote Similarity	NPD555	Phase 2
0.642	Remote Similarity	NPD8643	Discontinued
0.6418	Remote Similarity	NPD4435	Approved
0.6418	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6677	Suspended
0.6417	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD4677	Discontinued
0.6409	Remote Similarity	NPD2575	Approved
0.6402	Remote Similarity	NPD7600	Phase 2
0.64	Remote Similarity	NPD7715	Approved
0.64	Remote Similarity	NPD7714	Approved
0.6396	Remote Similarity	NPD4086	Phase 1
0.6395	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD6254	Approved
0.6394	Remote Similarity	NPD6256	Approved
0.6394	Remote Similarity	NPD6255	Approved
0.6391	Remote Similarity	NPD4806	Approved
0.6391	Remote Similarity	NPD4807	Approved
0.6389	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD8149	Discontinued
0.6386	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD5725	Approved
0.6383	Remote Similarity	NPD2515	Approved
0.6383	Remote Similarity	NPD3007	Approved
0.6383	Remote Similarity	NPD7011	Discontinued
0.6374	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD1725	Approved
0.6369	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD8351	Phase 2
0.6368	Remote Similarity	NPD4434	Approved
0.6364	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6309	Approved
0.6364	Remote Similarity	NPD6623	Phase 3
0.6364	Remote Similarity	NPD6310	Approved
0.6364	Remote Similarity	NPD6502	Phase 2
0.6364	Remote Similarity	NPD6311	Approved
0.6359	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD5204	Approved
0.6358	Remote Similarity	NPD3626	Phase 3
0.6353	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7599	Phase 2
0.6348	Remote Similarity	NPD3553	Approved
0.6348	Remote Similarity	NPD3554	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