NPASS Compound

Structure

CID314603 OpenBabel06191716122D 49 51 0 0 1 0 0 0 0 0999 V2000 -5.7792 -4.4300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2775 -5.2891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8132 -6.2710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6784 -5.3945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7425 -3.0022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6008 -1.5019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2399 0.9941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9022 0.2471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2617 0.7941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5864 -0.7001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2844 -3.5590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8265 -4.5410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1700 -0.0463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8553 1.5119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1275 -1.5459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5950 1.4950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7804 -4.4261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3204 -5.4022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7386 -2.0043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0307 -0.5522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9459 -0.1531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6083 -0.9002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4213 -3.0562 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8341 -3.5422 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3015 -0.5389 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0077 1.0090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8513 2.5108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4524 0.9826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8724 -1.5088 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8729 1.5083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5562 -3.5554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2937 -1.5484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0233 -3.0297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8646 -0.4992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7144 3.0136 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.1024 -1.7609 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7303 0.9958 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4446 -0.0265 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4291 -2.0466 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6993 -3.0430 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 0.0155 -2.0202 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0157 3.0067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3240 1.4727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8806 2.5082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5485 -4.5554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1576 -2.0522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8949 -3.5198 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7287 0.0041 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 19 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 21 2 0 0 0 0 10 22 2 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 20 1 0 0 0 0 14 27 1 0 0 0 0 15 20 2 0 0 0 0 15 36 1 0 0 0 0 16 28 1 0 0 0 0 16 37 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 22 36 1 0 0 0 0 23 11 1 6 0 0 0 23 31 1 0 0 0 0 23 39 1 0 0 0 0 24 12 1 1 0 0 0 24 33 1 0 0 0 0 24 40 1 0 0 0 0 25 13 1 6 0 0 0 25 32 1 0 0 0 0 25 38 1 0 0 0 0 26 14 1 6 0 0 0 26 30 1 0 0 0 0 26 41 1 0 0 0 0 27 35 2 0 0 0 0 27 43 1 0 0 0 0 28 38 2 3 0 0 0 28 44 1 0 0 0 0 29 19 1 6 0 0 0 29 34 1 0 0 0 0 29 42 1 0 0 0 0 30 37 2 3 0 0 0 30 45 1 0 0 0 0 31 40 2 3 0 0 0 31 46 1 0 0 0 0 32 39 2 3 0 0 0 32 47 1 0 0 0 0 33 42 2 3 0 0 0 33 48 1 0 0 0 0 34 41 2 3 0 0 0 34 49 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	682.38
Volume:	691.455
LogP:	1.175
LogD:	1.845
LogS:	-2.68
# Rotatable Bonds:	9
TPSA:	243.95
# H-Bond Aceptor:	15
# H-Bond Donor:	9
# Rings:	3
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.196
Synthetic Accessibility Score:	5.481
Fsp3:	0.559
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:	-4.446
MDCK Permeability:	1.5892173905740492e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.975
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.289
Plasma Protein Binding (PPB):	22.510501861572266%
Volume Distribution (VD):	0.579
Pgp-substrate:	62.70559310913086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.04
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.41
CYP2D6-inhibitor:	0.281
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.087
CYP3A4-substrate:	0.042

ADMET: Excretion

Clearance (CL):	1.473
Half-life (T1/2):	0.667

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.999
Drug-inuced Liver Injury (DILI):	0.89
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.133
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.215
Carcinogencity:	0.087
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC314603

Natural Product ID:	NPC314603
*Common Name:**	CHWWXLHSWFFSCF-LEGRXYIASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CHWWXLHSWFFSCF-LEGRXYIASA-N
Standard InCHI:	InChI=1S/C34H50N8O7/c1-17(2)11-23-31(46)40-24(12-18(3)4)33(48)42-29(19(5)6)34(49)41-26(14-27(35)43)30(45)37-16-28(44)38-25(32(47)39-23)13-20-15-36-22-10-8-7-9-21(20)22/h7-10,15,17-19,23-26,29,36H,11-14,16H2,1-6H3,(H2,35,43)(H,37,45)(H,38,44)(H,39,47)(H,40,46)(H,41,49)(H,42,48)/t23-,24+,25-,26-,29-/m0/s1
SMILES:	OC1=N[C@@H](Cc2c[nH]c3c2cccc3)C(=N[C@@H](CC(C)C)C(=N[C@@H](C(=N[C@H](C(=N[C@H](C(=NC1)O)CC(=N)O)O)C(C)C)O)CC(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3327051
PubChem CID:	NA
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
NPO13227.1	Streptomyces scopuliridis SCSIO ZJ46	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25072108]

☑ 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
MIC	5

Activity Type	# Activity
Cell Line	4
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[534612]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	100000.0	nM	PMID[534612]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[534612]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	>	100000.0	nM	PMID[534612]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	12.5	ug.mL-1	PMID[534612]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[534612]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[534612]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	128.0	ug.mL-1	PMID[534612]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	128.0	ug.mL-1	PMID[534612]

☑ 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 NPC314603 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	371
0.1-0.2	2964
0.2-0.3	18591
0.3-0.4	13243
0.4-0.5	3064
0.5-0.6	2330
0.6-0.7	1366
0.7-0.8	589
0.8-0.85	111
0.85-0.9	38
0.9-0.95	27
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9742	High Similarity	NPC160105
0.9367	High Similarity	NPC49954
0.9367	High Similarity	NPC474561
0.9226	High Similarity	NPC211572
0.9226	High Similarity	NPC80597
0.9226	High Similarity	NPC212376
0.9226	High Similarity	NPC70922
0.9226	High Similarity	NPC75540
0.9177	High Similarity	NPC282231
0.9161	High Similarity	NPC25008
0.9161	High Similarity	NPC469760
0.9161	High Similarity	NPC259644
0.9161	High Similarity	NPC469786
0.9161	High Similarity	NPC73952
0.9161	High Similarity	NPC469765
0.9161	High Similarity	NPC469763
0.9114	High Similarity	NPC279918
0.9068	High Similarity	NPC63751
0.9	High Similarity	NPC194640
0.8987	High Similarity	NPC469762
0.8924	High Similarity	NPC469785
0.8889	High Similarity	NPC54988
0.8882	High Similarity	NPC311276
0.8855	High Similarity	NPC59269
0.883	High Similarity	NPC213629
0.881	High Similarity	NPC233936
0.8774	High Similarity	NPC314372
0.875	High Similarity	NPC473640
0.8743	High Similarity	NPC248454
0.872	High Similarity	NPC201700
0.8683	High Similarity	NPC267885
0.8671	High Similarity	NPC24678
0.8671	High Similarity	NPC105818
0.8659	High Similarity	NPC155143
0.865	High Similarity	NPC40779
0.8645	High Similarity	NPC190296
0.8644	High Similarity	NPC171317
0.8623	High Similarity	NPC110500
0.8623	High Similarity	NPC203468
0.8623	High Similarity	NPC149155
0.8605	High Similarity	NPC235684
0.8605	High Similarity	NPC474707
0.8603	High Similarity	NPC475506
0.8596	High Similarity	NPC100321
0.8581	High Similarity	NPC469766
0.858	High Similarity	NPC248041
0.858	High Similarity	NPC283219
0.858	High Similarity	NPC230869
0.858	High Similarity	NPC126709
0.8571	High Similarity	NPC285469
0.8555	High Similarity	NPC317030
0.8538	High Similarity	NPC163055
0.8528	High Similarity	NPC131718
0.8516	High Similarity	NPC469768
0.8516	High Similarity	NPC469779
0.8516	High Similarity	NPC469783
0.8516	High Similarity	NPC469780
0.8516	High Similarity	NPC469784
0.8516	High Similarity	NPC469767
0.8516	High Similarity	NPC469761
0.8506	High Similarity	NPC173028
0.8506	High Similarity	NPC65215
0.8497	Intermediate Similarity	NPC94752
0.8494	Intermediate Similarity	NPC78020
0.8492	Intermediate Similarity	NPC293917
0.8453	Intermediate Similarity	NPC476874
0.8448	Intermediate Similarity	NPC204565
0.8418	Intermediate Similarity	NPC159856
0.8412	Intermediate Similarity	NPC14113
0.8412	Intermediate Similarity	NPC145885
0.8412	Intermediate Similarity	NPC84827
0.84	Intermediate Similarity	NPC321708
0.837	Intermediate Similarity	NPC323927
0.8364	Intermediate Similarity	NPC16667
0.8363	Intermediate Similarity	NPC213468
0.8352	Intermediate Similarity	NPC193761
0.8352	Intermediate Similarity	NPC95783
0.8333	Intermediate Similarity	NPC15102
0.8333	Intermediate Similarity	NPC280290
0.8333	Intermediate Similarity	NPC73767
0.8333	Intermediate Similarity	NPC194411
0.8323	Intermediate Similarity	NPC84911
0.8315	Intermediate Similarity	NPC474177
0.8314	Intermediate Similarity	NPC300688
0.8313	Intermediate Similarity	NPC471957
0.8313	Intermediate Similarity	NPC102423
0.8304	Intermediate Similarity	NPC151939
0.8304	Intermediate Similarity	NPC68354
0.8282	Intermediate Similarity	NPC207726
0.828	Intermediate Similarity	NPC107077
0.828	Intermediate Similarity	NPC223791
0.8276	Intermediate Similarity	NPC165495
0.8268	Intermediate Similarity	NPC133366
0.8258	Intermediate Similarity	NPC473342
0.8258	Intermediate Similarity	NPC477167
0.8258	Intermediate Similarity	NPC96102
0.8258	Intermediate Similarity	NPC261195
0.8258	Intermediate Similarity	NPC29886
0.8245	Intermediate Similarity	NPC75634
0.8242	Intermediate Similarity	NPC67056
0.8235	Intermediate Similarity	NPC313791
0.8229	Intermediate Similarity	NPC163421
0.8229	Intermediate Similarity	NPC188387
0.8225	Intermediate Similarity	NPC280548
0.8217	Intermediate Similarity	NPC110126
0.8205	Intermediate Similarity	NPC105127
0.8187	Intermediate Similarity	NPC37423
0.8187	Intermediate Similarity	NPC275305
0.8172	Intermediate Similarity	NPC54420
0.8171	Intermediate Similarity	NPC228835
0.8162	Intermediate Similarity	NPC473376
0.815	Intermediate Similarity	NPC55772
0.8133	Intermediate Similarity	NPC92796
0.8133	Intermediate Similarity	NPC135141
0.8129	Intermediate Similarity	NPC472123
0.8125	Intermediate Similarity	NPC314002
0.8122	Intermediate Similarity	NPC11445
0.8098	Intermediate Similarity	NPC53947
0.8095	Intermediate Similarity	NPC320968
0.8092	Intermediate Similarity	NPC111275
0.8085	Intermediate Similarity	NPC162860
0.8081	Intermediate Similarity	NPC469938
0.8079	Intermediate Similarity	NPC171171
0.8077	Intermediate Similarity	NPC229332
0.8072	Intermediate Similarity	NPC129721
0.807	Intermediate Similarity	NPC470498
0.8068	Intermediate Similarity	NPC204717
0.8066	Intermediate Similarity	NPC157828
0.8066	Intermediate Similarity	NPC195239
0.8057	Intermediate Similarity	NPC71037
0.8053	Intermediate Similarity	NPC75726
0.8053	Intermediate Similarity	NPC31385
0.8053	Intermediate Similarity	NPC110602
0.805	Intermediate Similarity	NPC279081
0.8049	Intermediate Similarity	NPC216713
0.8047	Intermediate Similarity	NPC470508
0.8046	Intermediate Similarity	NPC176199
0.8046	Intermediate Similarity	NPC215795
0.8043	Intermediate Similarity	NPC470497
0.8037	Intermediate Similarity	NPC37548
0.8034	Intermediate Similarity	NPC17059
0.8034	Intermediate Similarity	NPC46580
0.8033	Intermediate Similarity	NPC470499
0.8032	Intermediate Similarity	NPC314957
0.8011	Intermediate Similarity	NPC220765
0.8	Intermediate Similarity	NPC82295
0.8	Intermediate Similarity	NPC49217
0.8	Intermediate Similarity	NPC473763
0.8	Intermediate Similarity	NPC200214
0.8	Intermediate Similarity	NPC117244
0.7989	Intermediate Similarity	NPC478158
0.7978	Intermediate Similarity	NPC262898
0.7977	Intermediate Similarity	NPC329688
0.7977	Intermediate Similarity	NPC189812
0.7956	Intermediate Similarity	NPC477166
0.7956	Intermediate Similarity	NPC99666
0.7956	Intermediate Similarity	NPC304187
0.7953	Intermediate Similarity	NPC317430
0.7943	Intermediate Similarity	NPC11126
0.7937	Intermediate Similarity	NPC230002
0.7935	Intermediate Similarity	NPC265576
0.7923	Intermediate Similarity	NPC179701
0.7917	Intermediate Similarity	NPC206819
0.7917	Intermediate Similarity	NPC41257
0.7917	Intermediate Similarity	NPC56765
0.7917	Intermediate Similarity	NPC318065
0.7914	Intermediate Similarity	NPC143872
0.7914	Intermediate Similarity	NPC288838
0.791	Intermediate Similarity	NPC469358
0.791	Intermediate Similarity	NPC472108
0.791	Intermediate Similarity	NPC48938
0.791	Intermediate Similarity	NPC139291
0.7901	Intermediate Similarity	NPC243716
0.7895	Intermediate Similarity	NPC109447
0.788	Intermediate Similarity	NPC156704
0.788	Intermediate Similarity	NPC227582
0.7877	Intermediate Similarity	NPC315555
0.7874	Intermediate Similarity	NPC472586
0.7865	Intermediate Similarity	NPC472294
0.7857	Intermediate Similarity	NPC286427
0.7849	Intermediate Similarity	NPC252338
0.7846	Intermediate Similarity	NPC281049
0.7844	Intermediate Similarity	NPC470507
0.7844	Intermediate Similarity	NPC38736
0.7841	Intermediate Similarity	NPC219336
0.7828	Intermediate Similarity	NPC64216
0.7824	Intermediate Similarity	NPC54744
0.7821	Intermediate Similarity	NPC62510
0.7818	Intermediate Similarity	NPC187951
0.7818	Intermediate Similarity	NPC321911
0.7816	Intermediate Similarity	NPC34508
0.7814	Intermediate Similarity	NPC307963
0.7814	Intermediate Similarity	NPC106937
0.7809	Intermediate Similarity	NPC19679
0.7809	Intermediate Similarity	NPC472110
0.7809	Intermediate Similarity	NPC472109
0.7801	Intermediate Similarity	NPC271862
0.7798	Intermediate Similarity	NPC141353
0.7791	Intermediate Similarity	NPC242556
0.7784	Intermediate Similarity	NPC217372

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 NPC314603 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	516
0.2-0.3	1027
0.3-0.4	1487
0.4-0.5	2707
0.5-0.6	2141
0.6-0.7	852
0.7-0.8	194
0.8-0.85	24
0.85-0.9	9
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9618	High Similarity	NPD4184	Clinical (unspecified phase)
0.9281	High Similarity	NPD8110	Clinical (unspecified phase)
0.8994	High Similarity	NPD8431	Approved
0.8862	High Similarity	NPD6595	Phase 3
0.8757	High Similarity	NPD5728	Clinical (unspecified phase)
0.8647	High Similarity	NPD2094	Phase 2
0.8647	High Similarity	NPD2092	Phase 2
0.8647	High Similarity	NPD2095	Phase 2
0.8623	High Similarity	NPD482	Approved
0.8596	High Similarity	NPD2091	Phase 2
0.8596	High Similarity	NPD2096	Phase 2
0.8571	High Similarity	NPD749	Clinical (unspecified phase)
0.8564	High Similarity	NPD8272	Phase 2
0.8547	High Similarity	NPD6610	Clinical (unspecified phase)
0.8508	High Similarity	NPD8072	Approved
0.8492	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.8453	Intermediate Similarity	NPD8073	Approved
0.8452	Intermediate Similarity	NPD786	Approved
0.8421	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD2144	Approved
0.838	Intermediate Similarity	NPD7948	Phase 1
0.8372	Intermediate Similarity	NPD3038	Discontinued
0.8363	Intermediate Similarity	NPD4079	Approved
0.8363	Intermediate Similarity	NPD4076	Approved
0.8343	Intermediate Similarity	NPD750	Phase 2
0.8315	Intermediate Similarity	NPD7957	Phase 1
0.8315	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD3505	Approved
0.8304	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD3506	Approved
0.8294	Intermediate Similarity	NPD5065	Approved
0.827	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD8386	Phase 2
0.8228	Intermediate Similarity	NPD1722	Approved
0.814	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.8128	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD3100	Discontinued
0.8036	Intermediate Similarity	NPD8026	Phase 1
0.8012	Intermediate Similarity	NPD1325	Approved
0.8012	Intermediate Similarity	NPD1326	Approved
0.8	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD2172	Phase 1
0.7969	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7906	Intermediate Similarity	NPD7470	Discontinued
0.7887	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD4181	Approved
0.7879	Intermediate Similarity	NPD4462	Approved
0.7879	Intermediate Similarity	NPD4463	Approved
0.7874	Intermediate Similarity	NPD4128	Approved
0.7866	Intermediate Similarity	NPD4702	Approved
0.7866	Intermediate Similarity	NPD4703	Approved
0.7853	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD4638	Approved
0.7849	Intermediate Similarity	NPD4640	Approved
0.7849	Intermediate Similarity	NPD4639	Approved
0.7846	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD3961	Discontinued
0.7833	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD1038	Approved
0.7814	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD802	Phase 2
0.7784	Intermediate Similarity	NPD7970	Approved
0.7784	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3323	Discontinued
0.7772	Intermediate Similarity	NPD7944	Discontinued
0.7772	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD1403	Approved
0.7765	Intermediate Similarity	NPD1404	Approved
0.776	Intermediate Similarity	NPD3404	Approved
0.7759	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD2640	Approved
0.7746	Intermediate Similarity	NPD2641	Approved
0.7733	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD3717	Discontinued
0.7727	Intermediate Similarity	NPD4075	Phase 2
0.7688	Intermediate Similarity	NPD2639	Approved
0.7688	Intermediate Similarity	NPD2642	Approved
0.7679	Intermediate Similarity	NPD2837	Discontinued
0.7676	Intermediate Similarity	NPD7619	Phase 3
0.7676	Intermediate Similarity	NPD7618	Phase 3
0.7674	Intermediate Similarity	NPD5140	Approved
0.7674	Intermediate Similarity	NPD5138	Approved
0.766	Intermediate Similarity	NPD484	Approved
0.7644	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD5426	Phase 3
0.759	Intermediate Similarity	NPD8093	Discontinued
0.7574	Intermediate Similarity	NPD7711	Discontinued
0.7561	Intermediate Similarity	NPD1592	Phase 3
0.7557	Intermediate Similarity	NPD3609	Approved
0.7557	Intermediate Similarity	NPD3610	Approved
0.7551	Intermediate Similarity	NPD8094	Discontinued
0.7537	Intermediate Similarity	NPD7730	Approved
0.7537	Intermediate Similarity	NPD7731	Approved
0.7528	Intermediate Similarity	NPD5100	Phase 3
0.7527	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7271	Approved
0.7514	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5901	Discontinued
0.75	Intermediate Similarity	NPD6664	Approved
0.7486	Intermediate Similarity	NPD8123	Approved
0.7486	Intermediate Similarity	NPD8122	Approved
0.7475	Intermediate Similarity	NPD5612	Discontinued
0.7463	Intermediate Similarity	NPD7824	Approved
0.7459	Intermediate Similarity	NPD8408	Discontinued
0.7423	Intermediate Similarity	NPD8322	Phase 2
0.741	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6217	Discontinued
0.738	Intermediate Similarity	NPD4615	Phase 2
0.7377	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD8129	Discovery
0.7366	Intermediate Similarity	NPD5117	Phase 2
0.7366	Intermediate Similarity	NPD4499	Approved
0.7365	Intermediate Similarity	NPD5254	Discontinued
0.7356	Intermediate Similarity	NPD7950	Approved
0.7356	Intermediate Similarity	NPD7952	Approved
0.7356	Intermediate Similarity	NPD7953	Approved
0.7356	Intermediate Similarity	NPD7790	Approved
0.7356	Intermediate Similarity	NPD7791	Approved
0.7356	Intermediate Similarity	NPD7951	Approved
0.7356	Intermediate Similarity	NPD7789	Approved
0.7351	Intermediate Similarity	NPD8020	Approved
0.7351	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD8021	Approved
0.735	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD2844	Phase 3
0.7345	Intermediate Similarity	NPD5021	Discontinued
0.7337	Intermediate Similarity	NPD1661	Suspended
0.7333	Intermediate Similarity	NPD1392	Approved
0.7322	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD5596	Phase 2
0.7322	Intermediate Similarity	NPD5106	Approved
0.7322	Intermediate Similarity	NPD5105	Approved
0.7318	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7603	Discontinued
0.7314	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3654	Approved
0.7306	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD4427	Phase 2
0.7299	Intermediate Similarity	NPD5255	Approved
0.7297	Intermediate Similarity	NPD706	Phase 1
0.7297	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2119	Approved
0.7296	Intermediate Similarity	NPD991	Phase 2
0.7296	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2118	Approved
0.7292	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2580	Discontinued
0.7283	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8063	Discontinued
0.7267	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3475	Approved
0.7267	Intermediate Similarity	NPD3476	Approved
0.7263	Intermediate Similarity	NPD3116	Approved
0.7263	Intermediate Similarity	NPD3117	Approved
0.7262	Intermediate Similarity	NPD3813	Approved
0.7259	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD5862	Discovery
0.7246	Intermediate Similarity	NPD7781	Approved
0.7246	Intermediate Similarity	NPD7780	Approved
0.724	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD3330	Phase 1
0.7235	Intermediate Similarity	NPD4547	Phase 3
0.7234	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD8113	Phase 2
0.7209	Intermediate Similarity	NPD6158	Phase 2
0.7209	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2189	Approved
0.7208	Intermediate Similarity	NPD2187	Approved
0.7202	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4601	Approved
0.7202	Intermediate Similarity	NPD4600	Approved
0.7202	Intermediate Similarity	NPD2006	Phase 2
0.7196	Intermediate Similarity	NPD6665	Discontinued
0.7193	Intermediate Similarity	NPD2430	Phase 2
0.7193	Intermediate Similarity	NPD3575	Approved
0.7193	Intermediate Similarity	NPD3576	Approved
0.7189	Intermediate Similarity	NPD6178	Phase 3
0.7186	Intermediate Similarity	NPD5067	Phase 2
0.7186	Intermediate Similarity	NPD5066	Phase 2
0.7182	Intermediate Similarity	NPD5322	Clinical (unspecified phase)

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