NPASS Compound

Structure

NPC106235 OpenBabel07101718312D 56 58 0 0 1 0 0 0 0 0999 V2000 -10.8080 0.1360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2786 -7.1734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7375 -3.1586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2023 -4.8059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9059 0.7540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7649 -5.8351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4071 3.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9118 -4.9081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4470 -3.2608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5296 -2.1804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7254 -0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4071 0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0648 -0.5332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0707 -6.1952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2218 3.2902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 3.0823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7218 2.4242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0570 2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2117 0.3939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9944 -3.8277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1138 -0.2241 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8139 -5.5261 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4071 2.0878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9230 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1391 2.0878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4196 -0.5843 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2606 0.7029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0433 -3.5187 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3706 -0.8933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6060 -4.5480 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2731 1.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5411 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3491 -3.8788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8354 -2.5406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6750 2.0878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.3002 -4.1878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.6549 -4.2389 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.5785 -1.8714 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.0527 1.6810 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5175 0.0338 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5411 0.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1412 -2.9007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8843 -2.2315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6764 -1.2534 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2731 0.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 8 47 1 0 0 0 0 9 47 1 0 0 0 0 10 48 1 0 0 0 0 11 54 1 0 0 0 0 12 55 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 16 19 1 0 0 0 0 17 20 2 0 0 0 0 18 21 1 0 0 0 0 18 23 1 0 0 0 0 19 31 2 0 0 0 0 20 31 1 0 0 0 0 21 33 1 0 0 0 0 22 24 2 0 0 0 0 22 44 1 0 0 0 0 23 49 1 0 0 0 0 24 56 1 0 0 0 0 25 31 1 0 0 0 0 26 35 1 0 0 0 0 28 5 1 6 0 0 0 28 37 1 0 0 0 0 29 6 1 6 0 0 0 29 38 1 0 0 0 0 30 7 1 1 0 0 0 30 39 1 0 0 0 0 30 40 1 0 0 0 0 32 25 1 1 0 0 0 32 42 1 0 0 0 0 32 45 1 0 0 0 0 33 39 1 1 0 0 0 33 49 1 0 0 0 0 34 26 1 1 0 0 0 34 37 1 0 0 0 0 34 54 1 0 0 0 0 35 49 1 0 0 0 0 35 50 2 0 0 0 0 36 27 1 1 0 0 0 36 43 1 0 0 0 0 36 46 1 0 0 0 0 37 48 1 1 0 0 0 38 41 1 1 0 0 0 38 47 1 0 0 0 0 39 55 1 1 0 0 0 40 45 2 3 0 0 0 40 51 1 0 0 0 0 41 46 2 3 0 0 0 41 52 1 0 0 0 0 42 44 2 0 0 0 0 42 56 1 0 0 0 0 43 48 1 0 0 0 0 43 53 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	798.51
Volume:	840.117
LogP:	4.388
LogD:	3.981
LogS:	-4.204
# Rotatable Bonds:	26
TPSA:	133.41
# H-Bond Aceptor:	12
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.158
Synthetic Accessibility Score:	5.184
Fsp3:	0.698
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:	-5.072
MDCK Permeability:	1.2912250895169564e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.567
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.823
30% Bioavailability (F30%):	0.778

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	91.16265106201172%
Volume Distribution (VD):	1.317
Pgp-substrate:	1.2935785055160522%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.058
CYP2C19-inhibitor:	0.172
CYP2C19-substrate:	0.916
CYP2C9-inhibitor:	0.429
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.186
CYP3A4-inhibitor:	0.97
CYP3A4-substrate:	0.931

ADMET: Excretion

Clearance (CL):	7.234
Half-life (T1/2):	0.091

ADMET: Toxicity

hERG Blockers:	0.114
Human Hepatotoxicity (H-HT):	0.887
Drug-inuced Liver Injury (DILI):	0.873
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.585
Maximum Recommended Daily Dose:	0.283
Skin Sensitization:	0.025
Carcinogencity:	0.074
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC106235

Natural Product ID:	NPC106235
*Common Name:**	Symplostatin 1
IUPAC Name:	(2S,3S)-2-(dimethylamino)-N-[(2S)-1-[[(3R,4S,5S)-3-methoxy-1-[(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-[[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino]propyl]pyrrolidin-1-yl]-5-methyl-1-oxoheptan-4-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]-3-methylpentanamide
Synonyms:	Symplostatin 1
Standard InCHIKey:	OJSUENRPBJADBN-KJTFKGMVSA-N
Standard InCHI:	InChI=1S/C43H70N6O6S/c1-13-28(5)37(48(10)43(53)36(27(3)4)46-41(52)38(47(8)9)29(6)14-2)34(54-11)26-35(50)49-23-18-21-33(49)39(55-12)30(7)40(51)45-32(42-44-22-24-56-42)25-31-19-16-15-17-20-31/h15-17,19-20,22,24,27-30,32-34,36-39H,13-14,18,21,23,25-26H2,1-12H3,(H,45,51)(H,46,52)/t28-,29-,30+,32-,33-,34+,36-,37-,38-,39+/m0/s1
SMILES:	CC[C@@H]([C@H](N(C(=O)[C@H](C(C)C)N=C([C@H]([C@H](CC)C)N(C)C)O)C)[C@@H](CC(=O)N1CCC[C@H]1[C@@H]([C@H](C(=N[C@H](c1nccs1)Cc1ccccc1)O)C)OC)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501233
PubChem CID:	10887298
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0002010] Hybrid peptides

*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
NPO32764	symploca species vp642	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11473421]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11975485]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21446699]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31763840]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9748368]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
EC50	1
IC50	4
Others	7

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	3
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.15	nM	PMID[507703]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	0.34	nM	PMID[507703]
NPT2657	Cell Line	A10	Rattus norvegicus	EC50	=	0.6	nM	PMID[507703]
NPT730	Cell Line	MC-38	Mus musculus	T/C	=	0.0	%	PMID[507703]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.0003	ug.mL-1	PMID[507704]
NPT2657	Cell Line	A10	Rattus norvegicus	Activity	=	80.0	%	PMID[507704]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	1.5	nM	PMID[507705]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	T/C	=	0.0	%	PMID[507703]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	T/C	=	32.0	%	PMID[507703]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	T/C	=	36.0	%	PMID[507703]
NPT32	Organism	Mus musculus	Mus musculus	LD20	=	1.0	mg kg-1	PMID[507703]
NPT32	Organism	Mus musculus	Mus musculus	LD60	=	1.4	mg kg-1	PMID[507703]

☑ 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 NPC106235 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	250
0.1-0.2	1519
0.2-0.3	12780
0.3-0.4	20669
0.4-0.5	5066
0.5-0.6	2034
0.6-0.7	352
0.7-0.8	20
0.8-0.85	1
0.85-0.9	4
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC239660
0.8977	High Similarity	NPC161143
0.8144	Intermediate Similarity	NPC75498
0.7906	Intermediate Similarity	NPC165538
0.7828	Intermediate Similarity	NPC257511
0.7801	Intermediate Similarity	NPC329961
0.7801	Intermediate Similarity	NPC122427
0.7592	Intermediate Similarity	NPC96016
0.7554	Intermediate Similarity	NPC475920
0.7415	Intermediate Similarity	NPC475350
0.7415	Intermediate Similarity	NPC145178
0.7415	Intermediate Similarity	NPC14877
0.7308	Intermediate Similarity	NPC251036
0.7277	Intermediate Similarity	NPC161242
0.7263	Intermediate Similarity	NPC283783
0.7202	Intermediate Similarity	NPC25316
0.7202	Intermediate Similarity	NPC263485
0.7202	Intermediate Similarity	NPC229160
0.7196	Intermediate Similarity	NPC476103
0.7188	Intermediate Similarity	NPC475534
0.7188	Intermediate Similarity	NPC476080
0.715	Intermediate Similarity	NPC475330
0.7143	Intermediate Similarity	NPC24990
0.7136	Intermediate Similarity	NPC475196
0.7113	Intermediate Similarity	NPC174652
0.6983	Remote Similarity	NPC476978
0.6949	Remote Similarity	NPC89489
0.6914	Remote Similarity	NPC287401
0.6908	Remote Similarity	NPC475506
0.6875	Remote Similarity	NPC155143
0.6852	Remote Similarity	NPC79386
0.684	Remote Similarity	NPC478158
0.6839	Remote Similarity	NPC300315
0.6831	Remote Similarity	NPC105717
0.6811	Remote Similarity	NPC162104
0.6798	Remote Similarity	NPC473763
0.6798	Remote Similarity	NPC117244
0.6763	Remote Similarity	NPC473640
0.6761	Remote Similarity	NPC107077
0.6761	Remote Similarity	NPC223791
0.6761	Remote Similarity	NPC162860
0.6758	Remote Similarity	NPC322878
0.6735	Remote Similarity	NPC318930
0.6735	Remote Similarity	NPC317362
0.6713	Remote Similarity	NPC54744
0.6711	Remote Similarity	NPC469858
0.6705	Remote Similarity	NPC130309
0.6703	Remote Similarity	NPC478251
0.6703	Remote Similarity	NPC478252
0.6685	Remote Similarity	NPC248283
0.6684	Remote Similarity	NPC286551
0.6682	Remote Similarity	NPC478157
0.6667	Remote Similarity	NPC209509
0.6667	Remote Similarity	NPC110602
0.6667	Remote Similarity	NPC316008
0.6667	Remote Similarity	NPC5620
0.6667	Remote Similarity	NPC31385
0.6667	Remote Similarity	NPC75726
0.6667	Remote Similarity	NPC54420
0.6667	Remote Similarity	NPC313867
0.6652	Remote Similarity	NPC63279
0.665	Remote Similarity	NPC326407
0.665	Remote Similarity	NPC317725
0.6648	Remote Similarity	NPC161069
0.663	Remote Similarity	NPC314358
0.663	Remote Similarity	NPC262077
0.6623	Remote Similarity	NPC297642
0.6622	Remote Similarity	NPC253987
0.6621	Remote Similarity	NPC238945
0.662	Remote Similarity	NPC320968
0.6618	Remote Similarity	NPC213629
0.6613	Remote Similarity	NPC2501
0.6612	Remote Similarity	NPC314388
0.6612	Remote Similarity	NPC315283
0.6611	Remote Similarity	NPC471265
0.6611	Remote Similarity	NPC471264
0.6609	Remote Similarity	NPC478029
0.6596	Remote Similarity	NPC122590
0.6593	Remote Similarity	NPC269398
0.6593	Remote Similarity	NPC263493
0.659	Remote Similarity	NPC6975
0.659	Remote Similarity	NPC46427
0.6575	Remote Similarity	NPC98424
0.6575	Remote Similarity	NPC476133
0.6575	Remote Similarity	NPC470884
0.6575	Remote Similarity	NPC92784
0.6575	Remote Similarity	NPC178662
0.6571	Remote Similarity	NPC100321
0.6571	Remote Similarity	NPC293917
0.6566	Remote Similarity	NPC477462
0.6559	Remote Similarity	NPC240848
0.6554	Remote Similarity	NPC200589
0.6532	Remote Similarity	NPC252878
0.6524	Remote Similarity	NPC171317
0.6524	Remote Similarity	NPC129666
0.6522	Remote Similarity	NPC478028
0.6516	Remote Similarity	NPC281049
0.6514	Remote Similarity	NPC75634
0.6512	Remote Similarity	NPC200964
0.6505	Remote Similarity	NPC138775
0.6488	Remote Similarity	NPC4910
0.6486	Remote Similarity	NPC471680
0.6474	Remote Similarity	NPC202521
0.6459	Remote Similarity	NPC294693
0.6458	Remote Similarity	NPC297145
0.6458	Remote Similarity	NPC197743
0.6452	Remote Similarity	NPC475390
0.6441	Remote Similarity	NPC319766
0.6441	Remote Similarity	NPC275393
0.6432	Remote Similarity	NPC52748
0.6425	Remote Similarity	NPC255447
0.6419	Remote Similarity	NPC473376
0.6418	Remote Similarity	NPC64436
0.6416	Remote Similarity	NPC476990
0.6416	Remote Similarity	NPC19170
0.6398	Remote Similarity	NPC315266
0.6391	Remote Similarity	NPC165743
0.6359	Remote Similarity	NPC163392
0.6359	Remote Similarity	NPC239762
0.6348	Remote Similarity	NPC475969
0.6348	Remote Similarity	NPC474877
0.6348	Remote Similarity	NPC475859
0.634	Remote Similarity	NPC469898
0.6339	Remote Similarity	NPC315804
0.6339	Remote Similarity	NPC313804
0.6332	Remote Similarity	NPC297862
0.633	Remote Similarity	NPC225648
0.633	Remote Similarity	NPC145113
0.633	Remote Similarity	NPC329761
0.6329	Remote Similarity	NPC329731
0.6329	Remote Similarity	NPC17059
0.6326	Remote Similarity	NPC476874
0.6318	Remote Similarity	NPC469938
0.6316	Remote Similarity	NPC475168
0.6316	Remote Similarity	NPC7817
0.6313	Remote Similarity	NPC473322
0.6311	Remote Similarity	NPC49051
0.6308	Remote Similarity	NPC469901
0.6304	Remote Similarity	NPC470730
0.6304	Remote Similarity	NPC477175
0.6304	Remote Similarity	NPC470729
0.6304	Remote Similarity	NPC477176
0.63	Remote Similarity	NPC64216
0.6296	Remote Similarity	NPC143325
0.6296	Remote Similarity	NPC471821
0.6296	Remote Similarity	NPC471820
0.6293	Remote Similarity	NPC220852
0.629	Remote Similarity	NPC139326
0.6281	Remote Similarity	NPC473000
0.628	Remote Similarity	NPC94752
0.6277	Remote Similarity	NPC477177
0.627	Remote Similarity	NPC268841
0.627	Remote Similarity	NPC46098
0.627	Remote Similarity	NPC307357
0.6269	Remote Similarity	NPC469903
0.625	Remote Similarity	NPC89987
0.6244	Remote Similarity	NPC471052
0.6244	Remote Similarity	NPC471051
0.6244	Remote Similarity	NPC471053
0.623	Remote Similarity	NPC478253
0.623	Remote Similarity	NPC141050
0.623	Remote Similarity	NPC478254
0.6226	Remote Similarity	NPC184933
0.6226	Remote Similarity	NPC59827
0.6222	Remote Similarity	NPC477714
0.6222	Remote Similarity	NPC111428
0.6218	Remote Similarity	NPC470902
0.6215	Remote Similarity	NPC175726
0.6215	Remote Similarity	NPC474082
0.6213	Remote Similarity	NPC285343
0.6207	Remote Similarity	NPC470546
0.6207	Remote Similarity	NPC469900
0.6203	Remote Similarity	NPC176226
0.6193	Remote Similarity	NPC73655
0.6185	Remote Similarity	NPC263117
0.6185	Remote Similarity	NPC242872
0.6185	Remote Similarity	NPC125181
0.6184	Remote Similarity	NPC228835
0.6183	Remote Similarity	NPC476259
0.6181	Remote Similarity	NPC254700
0.6174	Remote Similarity	NPC24370
0.6174	Remote Similarity	NPC319232
0.6166	Remote Similarity	NPC202198
0.6166	Remote Similarity	NPC262166
0.6158	Remote Similarity	NPC136797
0.615	Remote Similarity	NPC469427
0.615	Remote Similarity	NPC49195
0.615	Remote Similarity	NPC469426
0.6149	Remote Similarity	NPC470545
0.6145	Remote Similarity	NPC101719
0.6142	Remote Similarity	NPC473003
0.6142	Remote Similarity	NPC469902
0.614	Remote Similarity	NPC477527
0.614	Remote Similarity	NPC149708
0.6139	Remote Similarity	NPC328494
0.6134	Remote Similarity	NPC473002
0.6129	Remote Similarity	NPC54537
0.612	Remote Similarity	NPC314056
0.6117	Remote Similarity	NPC197682
0.6117	Remote Similarity	NPC77905

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 NPC106235 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	475
0.2-0.3	831
0.3-0.4	2373
0.4-0.5	4032
0.5-0.6	1193
0.6-0.7	78
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD8339	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD6348	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6349	Phase 1
0.7402	Intermediate Similarity	NPD8071	Approved
0.7396	Intermediate Similarity	NPD7977	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD8172	Phase 2
0.7384	Intermediate Similarity	NPD8173	Phase 2
0.7333	Intermediate Similarity	NPD6632	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8260	Approved
0.7143	Intermediate Similarity	NPD6092	Discontinued
0.7136	Intermediate Similarity	NPD4949	Discontinued
0.7064	Intermediate Similarity	NPD7711	Discontinued
0.7039	Intermediate Similarity	NPD7321	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD8272	Phase 2
0.6798	Remote Similarity	NPD2893	Phase 3
0.678	Remote Similarity	NPD7944	Discontinued
0.6743	Remote Similarity	NPD4125	Approved
0.6653	Remote Similarity	NPD6627	Discontinued
0.6648	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5461	Discontinued
0.6607	Remote Similarity	NPD8075	Discontinued
0.659	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6915	Approved
0.6571	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD2437	Approved
0.6522	Remote Similarity	NPD2436	Approved
0.6517	Remote Similarity	NPD7104	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD8169	Discontinued
0.6479	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5638	Approved
0.6455	Remote Similarity	NPD7970	Approved
0.6444	Remote Similarity	NPD6173	Approved
0.6443	Remote Similarity	NPD2511	Approved
0.6419	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD1004	Phase 2
0.6402	Remote Similarity	NPD1005	Phase 2
0.6398	Remote Similarity	NPD5265	Approved
0.6398	Remote Similarity	NPD5264	Approved
0.6396	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD8271	Discontinued
0.6392	Remote Similarity	NPD4557	Approved
0.6389	Remote Similarity	NPD7001	Phase 3
0.6382	Remote Similarity	NPD8284	Discontinued
0.635	Remote Similarity	NPD7965	Phase 2
0.635	Remote Similarity	NPD8124	Phase 3
0.635	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.635	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD8072	Approved
0.6292	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD3469	Phase 3
0.6289	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD6044	Discontinued
0.6286	Remote Similarity	NPD6665	Discontinued
0.6284	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5189	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7470	Discontinued
0.6243	Remote Similarity	NPD8323	Discontinued
0.6238	Remote Similarity	NPD6659	Phase 2
0.6238	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5323	Approved
0.622	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4126	Approved
0.6215	Remote Similarity	NPD2584	Suspended
0.6214	Remote Similarity	NPD8069	Phase 3
0.621	Remote Similarity	NPD7834	Approved
0.6209	Remote Similarity	NPD3288	Approved
0.6205	Remote Similarity	NPD5634	Approved
0.6204	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD2022	Approved
0.6203	Remote Similarity	NPD7816	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD8261	Discontinued
0.6183	Remote Similarity	NPD3480	Approved
0.6182	Remote Similarity	NPD7981	Discontinued
0.6175	Remote Similarity	NPD8073	Approved
0.6172	Remote Similarity	NPD6891	Phase 2
0.6161	Remote Similarity	NPD5077	Approved
0.6161	Remote Similarity	NPD5076	Approved
0.6158	Remote Similarity	NPD2055	Phase 3
0.6158	Remote Similarity	NPD2054	Approved
0.6154	Remote Similarity	NPD2044	Approved
0.6154	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD2048	Approved
0.6154	Remote Similarity	NPD2045	Approved
0.6154	Remote Similarity	NPD2051	Approved
0.6154	Remote Similarity	NPD2047	Approved
0.6154	Remote Similarity	NPD2043	Approved
0.6154	Remote Similarity	NPD21	Approved
0.6154	Remote Similarity	NPD2046	Approved
0.615	Remote Similarity	NPD4508	Discontinued
0.6146	Remote Similarity	NPD6368	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD2957	Phase 2
0.6143	Remote Similarity	NPD2015	Discontinued
0.6141	Remote Similarity	NPD8416	Discontinued
0.6138	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD4648	Approved
0.6134	Remote Similarity	NPD4647	Approved
0.6134	Remote Similarity	NPD4646	Approved
0.6133	Remote Similarity	NPD7496	Phase 2
0.6128	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6347	Phase 2
0.6121	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.612	Remote Similarity	NPD5299	Approved
0.6117	Remote Similarity	NPD2088	Approved
0.6117	Remote Similarity	NPD2087	Approved
0.6114	Remote Similarity	NPD5230	Approved
0.6114	Remote Similarity	NPD8356	Approved
0.6114	Remote Similarity	NPD5229	Approved
0.6111	Remote Similarity	NPD5665	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD8119	Discontinued
0.6111	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6857	Phase 3
0.6108	Remote Similarity	NPD8643	Discontinued
0.6106	Remote Similarity	NPD7482	Phase 2
0.6106	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD7483	Phase 2
0.6103	Remote Similarity	NPD2717	Phase 2
0.6099	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD3988	Approved
0.6094	Remote Similarity	NPD3987	Approved
0.6091	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD7791	Approved
0.6085	Remote Similarity	NPD7950	Approved
0.6085	Remote Similarity	NPD7790	Approved
0.6085	Remote Similarity	NPD7953	Approved
0.6085	Remote Similarity	NPD7951	Approved
0.6085	Remote Similarity	NPD7789	Approved
0.6085	Remote Similarity	NPD7952	Approved
0.6078	Remote Similarity	NPD7730	Approved
0.6078	Remote Similarity	NPD7731	Approved
0.6077	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD1745	Approved
0.6052	Remote Similarity	NPD7781	Approved
0.6052	Remote Similarity	NPD7780	Approved
0.6045	Remote Similarity	NPD4903	Approved
0.6045	Remote Similarity	NPD4906	Approved
0.6045	Remote Similarity	NPD4905	Approved
0.6043	Remote Similarity	NPD2321	Approved
0.604	Remote Similarity	NPD6303	Approved
0.604	Remote Similarity	NPD6304	Approved
0.6037	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6035	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6035	Remote Similarity	NPD5523	Approved
0.6035	Remote Similarity	NPD5524	Approved
0.6026	Remote Similarity	NPD7824	Approved
0.6021	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD3449	Discontinued
0.6019	Remote Similarity	NPD8021	Approved
0.6019	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7490	Discontinued
0.6019	Remote Similarity	NPD8020	Approved
0.6018	Remote Similarity	NPD4904	Approved
0.6018	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.601	Remote Similarity	NPD5613	Approved
0.601	Remote Similarity	NPD5614	Approved
0.601	Remote Similarity	NPD963	Discontinued
0.6009	Remote Similarity	NPD8430	Approved
0.6009	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6008	Remote Similarity	NPD6205	Discontinued
0.6	Remote Similarity	NPD6888	Discontinued
0.6	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.5992	Remote Similarity	NPD8247	Approved
0.5992	Remote Similarity	NPD8246	Approved
0.5991	Remote Similarity	NPD7271	Approved
0.599	Remote Similarity	NPD5636	Discontinued
0.5989	Remote Similarity	NPD1646	Approved
0.5989	Remote Similarity	NPD5004	Approved
0.5985	Remote Similarity	NPD8107	Approved
0.598	Remote Similarity	NPD4567	Approved
0.598	Remote Similarity	NPD4566	Approved
0.5974	Remote Similarity	NPD6718	Discontinued
0.5968	Remote Similarity	NPD8265	Approved
0.5965	Remote Similarity	NPD5818	Discontinued
0.5964	Remote Similarity	NPD7665	Phase 2
0.5964	Remote Similarity	NPD7666	Phase 3
0.5963	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD6999	Discontinued
0.5961	Remote Similarity	NPD6916	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD8374	Phase 3
0.5952	Remote Similarity	NPD2091	Phase 2
0.5952	Remote Similarity	NPD2096	Phase 2
0.5951	Remote Similarity	NPD750	Phase 2
0.5949	Remote Similarity	NPD7613	Discontinued
0.5949	Remote Similarity	NPD3575	Approved
0.5949	Remote Similarity	NPD3576	Approved
0.5946	Remote Similarity	NPD2849	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.594	Remote Similarity	NPD7826	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