NPASS Compound

Structure

CID198893 OpenBabel06191715582D 77 86 0 0 1 0 0 0 0 0999 V2000 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5885 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7224 -7.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -7.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3923 -9.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -9.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 -8.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7224 -8.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 -7.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -8.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -7.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -7.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.9904 -7.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -7.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 -8.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5263 -7.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -7.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -8.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -8.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -7.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 15.5885 -9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 8 10 2 0 0 0 0 8 30 1 0 0 0 0 9 12 1 0 0 0 0 9 29 1 0 0 0 0 10 36 1 0 0 0 0 11 13 1 0 0 0 0 11 35 1 0 0 0 0 12 39 1 0 0 0 0 13 40 1 0 0 0 0 14 21 2 0 0 0 0 14 28 1 0 0 0 0 15 21 1 0 0 0 0 15 31 2 0 0 0 0 16 28 1 0 0 0 0 16 32 1 0 0 0 0 17 33 1 0 0 0 0 17 41 1 0 0 0 0 18 34 1 0 0 0 0 18 42 1 0 0 0 0 19 37 1 0 0 0 0 19 43 1 0 0 0 0 20 38 1 0 0 0 0 20 44 1 0 0 0 0 22 2 1 1 0 0 0 22 29 1 0 0 0 0 22 66 1 0 0 0 0 23 3 1 1 0 0 0 23 35 1 0 0 0 0 23 67 1 0 0 0 0 24 4 1 1 0 0 0 24 50 1 0 0 0 0 24 68 1 0 0 0 0 25 5 1 1 0 0 0 25 51 1 0 0 0 0 25 69 1 0 0 0 0 26 6 1 1 0 0 0 26 54 1 0 0 0 0 26 70 1 0 0 0 0 27 7 1 1 0 0 0 27 55 1 0 0 0 0 27 71 1 0 0 0 0 28 45 2 0 0 0 0 29 56 1 1 0 0 0 30 46 2 0 0 0 0 30 57 1 0 0 0 0 31 45 1 0 0 0 0 31 58 1 0 0 0 0 32 47 1 0 0 0 0 32 59 1 6 0 0 0 33 54 1 0 0 0 0 33 60 1 1 0 0 0 34 55 1 0 0 0 0 34 61 1 1 0 0 0 35 72 1 1 0 0 0 36 48 2 0 0 0 0 36 73 1 0 0 0 0 37 50 1 0 0 0 0 37 74 1 1 0 0 0 38 51 1 0 0 0 0 38 75 1 1 0 0 0 39 66 1 0 0 0 0 39 74 1 6 0 0 0 40 67 1 0 0 0 0 40 75 1 6 0 0 0 41 70 1 0 0 0 0 41 72 1 1 0 0 0 42 71 1 0 0 0 0 42 73 1 1 0 0 0 43 68 1 0 0 0 0 43 76 1 1 0 0 0 44 69 1 0 0 0 0 44 77 1 1 0 0 0 45 49 1 0 0 0 0 46 48 1 0 0 0 0 46 53 1 0 0 0 0 47 49 2 0 0 0 0 47 52 1 0 0 0 0 48 52 1 0 0 0 0 49 53 1 0 0 0 0 50 62 1 6 0 0 0 51 63 1 6 0 0 0 52 64 2 0 0 0 0 53 65 2 0 0 0 0 54 76 1 6 0 0 0 55 77 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1086.47
Volume:	1043.928
LogP:	6.276
LogD:	3.033
LogS:	-5.915
# Rotatable Bonds:	12
TPSA:	313.06
# H-Bond Aceptor:	22
# H-Bond Donor:	10
# Rings:	10
# Heavy Atoms:	22

MedChem Properties

QED Drug-Likeness Score:	0.052
Synthetic Accessibility Score:	6.811
Fsp3:	0.673
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.223
MDCK Permeability:	0.00021440477576106787
Pgp-inhibitor:	0.0
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.096
Plasma Protein Binding (PPB):	93.71587371826172%
Volume Distribution (VD):	-0.341
Pgp-substrate:	11.415776252746582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.985
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.503
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.141
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.757

ADMET: Excretion

Clearance (CL):	1.345
Half-life (T1/2):	0.162

ADMET: Toxicity

hERG Blockers:	0.318
Human Hepatotoxicity (H-HT):	0.215
Drug-inuced Liver Injury (DILI):	0.99
AMES Toxicity:	0.573
Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.966
Carcinogencity:	0.894
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.808

Download Data

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

Natural Product: NPC198893

Natural Product ID:	NPC198893
*Common Name:**	Landomycin A
IUPAC Name:	(6R)-1,6,11-trihydroxy-8-[(2S,4R,5S,6R)-4-hydroxy-5-[(2S,4R,5R,6R)-5-hydroxy-4-[(2S,5S,6S)-5-[(2S,4R,5S,6R)-4-hydroxy-5-[(2S,4R,5R,6R)-5-hydroxy-4-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-3-methyl-5,6-dihydrobenzo[a]anthracene-7,12-dione
Synonyms:	Landomycin A
Standard InCHIKey:	YMSZNAXJMXNNPT-OPAYXXSESA-N
Standard InCHI:	InChI=1S/C55H74O22/c1-21-14-28-16-32(59)47-49(45(28)31(58)15-21)53(65)46-30(57)8-10-36(48(46)52(47)64)73-42-18-34(61)55(27(7)71-42)77-44-20-38(51(63)25(5)69-44)75-40-13-11-35(23(3)67-40)72-41-17-33(60)54(26(6)70-41)76-43-19-37(50(62)24(4)68-43)74-39-12-9-29(56)22(2)66-39/h8,10,14-15,22-27,29,32-35,37-44,50-51,54-63H,9,11-13,16-20H2,1-7H3/t22-,23-,24+,25+,26+,27+,29-,32+,33+,34+,35-,37+,38+,39-,40-,41-,42-,43-,44-,50+,51+,54+,55+/m0/s1
SMILES:	Cc1cc2C[C@H](C3=C(c2c(c1)O)C(=O)c1c(ccc(c1C3=O)O[C@H]1C[C@H]([C@@H]([C@@H](C)O1)O[C@H]1C[C@H]([C@@H]([C@@H](C)O1)O)O[C@H]1CC[C@@H]([C@H](C)O1)O[C@H]1C[C@H]([C@@H]([C@@H](C)O1)O[C@H]1C[C@H]([C@@H]([C@@H](C)O1)O)O[C@H]1CC[C@@H]([C@H](C)O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668770
PubChem CID:	9988748
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO19685	Streptomyces cyanogenus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21188999]
NPO19685	Streptomyces cyanogenus	Species	Streptomycetaceae	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
GI50	2
IC50	2
Others	9

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2500.0	nM	PMID[512842]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	550.5	nM	PMID[512843]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	4109.0	nM	PMID[512843]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	10000.0	c.p.m./Abs	PMID[512841]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	45000.0	c.p.m./Abs	PMID[512841]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	65000.0	c.p.m./Abs	PMID[512841]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	5000.0	c.p.m./Abs	PMID[512841]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	30000.0	c.p.m./Abs	PMID[512841]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	60000.0	c.p.m./Abs	PMID[512841]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	0.0	c.p.m./Abs	PMID[512841]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	20000.0	c.p.m./Abs	PMID[512841]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1400.0	nM	PMID[512842]

☑ 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 NPC198893 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	445
0.1-0.2	1644
0.2-0.3	3484
0.3-0.4	8406
0.4-0.5	9003
0.5-0.6	6754
0.6-0.7	8109
0.7-0.8	4480
0.8-0.85	270
0.85-0.9	78
0.9-0.95	14
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC232818
1.0	High Similarity	NPC314489
0.9817	High Similarity	NPC307754
0.9817	High Similarity	NPC223735
0.9816	High Similarity	NPC315619
0.9693	High Similarity	NPC246274
0.9512	High Similarity	NPC63470
0.9471	High Similarity	NPC292706
0.9471	High Similarity	NPC224557
0.9353	High Similarity	NPC85316
0.9353	High Similarity	NPC197357
0.9294	High Similarity	NPC58538
0.9176	High Similarity	NPC289876
0.9176	High Similarity	NPC102053
0.9152	High Similarity	NPC146837
0.9152	High Similarity	NPC278329
0.9059	High Similarity	NPC203751
0.9042	High Similarity	NPC178281
0.9036	High Similarity	NPC212099
0.9036	High Similarity	NPC101116
0.9	High Similarity	NPC131405
0.8983	High Similarity	NPC48474
0.8982	High Similarity	NPC17432
0.8971	High Similarity	NPC241847
0.8953	High Similarity	NPC76112
0.8953	High Similarity	NPC170018
0.8953	High Similarity	NPC92403
0.8953	High Similarity	NPC66820
0.8909	High Similarity	NPC177742
0.8864	High Similarity	NPC87583
0.8857	High Similarity	NPC476203
0.8851	High Similarity	NPC187441
0.8851	High Similarity	NPC283980
0.8844	High Similarity	NPC475246
0.8844	High Similarity	NPC46958
0.8837	High Similarity	NPC85368
0.881	High Similarity	NPC216752
0.88	High Similarity	NPC164047
0.88	High Similarity	NPC470448
0.88	High Similarity	NPC477860
0.88	High Similarity	NPC470452
0.88	High Similarity	NPC475161
0.88	High Similarity	NPC470453
0.8786	High Similarity	NPC3718
0.8743	High Similarity	NPC53139
0.8743	High Similarity	NPC245059
0.8743	High Similarity	NPC84494
0.8736	High Similarity	NPC176246
0.8728	High Similarity	NPC199357
0.8728	High Similarity	NPC213052
0.8722	High Similarity	NPC314459
0.8722	High Similarity	NPC470199
0.8706	High Similarity	NPC99216
0.8698	High Similarity	NPC56735
0.8698	High Similarity	NPC61594
0.8686	High Similarity	NPC470581
0.8686	High Similarity	NPC115447
0.8686	High Similarity	NPC83331
0.8686	High Similarity	NPC470582
0.8671	High Similarity	NPC5029
0.8671	High Similarity	NPC288152
0.8671	High Similarity	NPC137871
0.8671	High Similarity	NPC76128
0.8671	High Similarity	NPC271385
0.8671	High Similarity	NPC9002
0.8671	High Similarity	NPC111536
0.8671	High Similarity	NPC257011
0.8671	High Similarity	NPC30432
0.8667	High Similarity	NPC321046
0.8655	High Similarity	NPC178173
0.8655	High Similarity	NPC70441
0.8647	High Similarity	NPC147596
0.8636	High Similarity	NPC114257
0.8636	High Similarity	NPC299149
0.8636	High Similarity	NPC153578
0.8636	High Similarity	NPC72783
0.8636	High Similarity	NPC277710
0.8626	High Similarity	NPC470196
0.8626	High Similarity	NPC470193
0.8626	High Similarity	NPC470200
0.8626	High Similarity	NPC470197
0.8626	High Similarity	NPC470194
0.8626	High Similarity	NPC316274
0.8626	High Similarity	NPC282474
0.8626	High Similarity	NPC470198
0.8626	High Similarity	NPC470195
0.8626	High Similarity	NPC314687
0.8621	High Similarity	NPC65118
0.8613	High Similarity	NPC241874
0.8613	High Similarity	NPC210808
0.8613	High Similarity	NPC199079
0.8611	High Similarity	NPC314672
0.858	High Similarity	NPC266513
0.858	High Similarity	NPC477683
0.858	High Similarity	NPC477682
0.8571	High Similarity	NPC470667
0.8571	High Similarity	NPC68381
0.8571	High Similarity	NPC102028
0.8571	High Similarity	NPC199533
0.8571	High Similarity	NPC63105
0.8571	High Similarity	NPC19056
0.8571	High Similarity	NPC186800
0.8571	High Similarity	NPC470454
0.8571	High Similarity	NPC470583
0.8563	High Similarity	NPC183441
0.8563	High Similarity	NPC270027
0.8555	High Similarity	NPC259905
0.8555	High Similarity	NPC222455
0.8547	High Similarity	NPC229817
0.8547	High Similarity	NPC475352
0.8547	High Similarity	NPC473686
0.8547	High Similarity	NPC475220
0.8547	High Similarity	NPC221140
0.8547	High Similarity	NPC178851
0.8531	High Similarity	NPC473895
0.8529	High Similarity	NPC132737
0.8523	High Similarity	NPC475233
0.8514	High Similarity	NPC154986
0.8506	High Similarity	NPC251144
0.8506	High Similarity	NPC298778
0.8506	High Similarity	NPC241387
0.8503	High Similarity	NPC470331
0.8488	Intermediate Similarity	NPC280923
0.8488	Intermediate Similarity	NPC478022
0.8488	Intermediate Similarity	NPC478020
0.8488	Intermediate Similarity	NPC478026
0.848	Intermediate Similarity	NPC473961
0.848	Intermediate Similarity	NPC190450
0.8475	Intermediate Similarity	NPC475261
0.8471	Intermediate Similarity	NPC328093
0.8466	Intermediate Similarity	NPC142996
0.8462	Intermediate Similarity	NPC208651
0.8462	Intermediate Similarity	NPC206641
0.8457	Intermediate Similarity	NPC267254
0.8457	Intermediate Similarity	NPC156977
0.8457	Intermediate Similarity	NPC301683
0.8453	Intermediate Similarity	NPC478035
0.8453	Intermediate Similarity	NPC473618
0.8448	Intermediate Similarity	NPC291795
0.8448	Intermediate Similarity	NPC207574
0.8448	Intermediate Similarity	NPC297195
0.8439	Intermediate Similarity	NPC475174
0.8436	Intermediate Similarity	NPC293227
0.8436	Intermediate Similarity	NPC478001
0.8436	Intermediate Similarity	NPC473717
0.8436	Intermediate Similarity	NPC473631
0.8436	Intermediate Similarity	NPC475662
0.843	Intermediate Similarity	NPC257566
0.843	Intermediate Similarity	NPC124155
0.843	Intermediate Similarity	NPC127415
0.843	Intermediate Similarity	NPC311850
0.8427	Intermediate Similarity	NPC212290
0.8418	Intermediate Similarity	NPC469345
0.8418	Intermediate Similarity	NPC255799
0.8412	Intermediate Similarity	NPC57072
0.8412	Intermediate Similarity	NPC231475
0.8412	Intermediate Similarity	NPC186113
0.8409	Intermediate Similarity	NPC98776
0.8409	Intermediate Similarity	NPC51774
0.8409	Intermediate Similarity	NPC236191
0.8409	Intermediate Similarity	NPC25724
0.8409	Intermediate Similarity	NPC168789
0.8409	Intermediate Similarity	NPC239549
0.8402	Intermediate Similarity	NPC283480
0.8402	Intermediate Similarity	NPC148323
0.84	Intermediate Similarity	NPC472129
0.84	Intermediate Similarity	NPC293004
0.84	Intermediate Similarity	NPC194483
0.84	Intermediate Similarity	NPC52353
0.84	Intermediate Similarity	NPC280385
0.84	Intermediate Similarity	NPC43434
0.84	Intermediate Similarity	NPC470580
0.8398	Intermediate Similarity	NPC179947
0.8398	Intermediate Similarity	NPC105591
0.8393	Intermediate Similarity	NPC185103
0.8391	Intermediate Similarity	NPC103633
0.8391	Intermediate Similarity	NPC249977
0.8389	Intermediate Similarity	NPC49690
0.8389	Intermediate Similarity	NPC318119
0.8389	Intermediate Similarity	NPC148710
0.8382	Intermediate Similarity	NPC470735
0.8382	Intermediate Similarity	NPC329647
0.8372	Intermediate Similarity	NPC44947
0.8372	Intermediate Similarity	NPC97637
0.8372	Intermediate Similarity	NPC187934
0.8372	Intermediate Similarity	NPC475382
0.8363	Intermediate Similarity	NPC97285
0.8363	Intermediate Similarity	NPC142860
0.8363	Intermediate Similarity	NPC271270
0.8363	Intermediate Similarity	NPC246469
0.8362	Intermediate Similarity	NPC70862
0.8362	Intermediate Similarity	NPC86809
0.8362	Intermediate Similarity	NPC146803
0.8362	Intermediate Similarity	NPC232412
0.8362	Intermediate Similarity	NPC474345
0.8362	Intermediate Similarity	NPC98667
0.8362	Intermediate Similarity	NPC198199
0.8361	Intermediate Similarity	NPC478034
0.8361	Intermediate Similarity	NPC264302
0.8352	Intermediate Similarity	NPC13989

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 NPC198893 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	387
0.1-0.2	941
0.2-0.3	1802
0.3-0.4	2794
0.4-0.5	1945
0.5-0.6	895
0.6-0.7	298
0.7-0.8	79
0.8-0.85	7
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8953	High Similarity	NPD8312	Approved
0.8953	High Similarity	NPD8313	Approved
0.8603	High Similarity	NPD7879	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD7074	Phase 3
0.8287	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8192	Intermediate Similarity	NPD7472	Approved
0.8156	Intermediate Similarity	NPD7808	Phase 3
0.8148	Intermediate Similarity	NPD7696	Phase 3
0.8148	Intermediate Similarity	NPD7697	Approved
0.8148	Intermediate Similarity	NPD7698	Approved
0.8136	Intermediate Similarity	NPD7054	Approved
0.8135	Intermediate Similarity	NPD7783	Phase 2
0.8135	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD7251	Discontinued
0.8101	Intermediate Similarity	NPD6559	Discontinued
0.8085	Intermediate Similarity	NPD6782	Approved
0.8085	Intermediate Similarity	NPD6780	Approved
0.8085	Intermediate Similarity	NPD6776	Approved
0.8085	Intermediate Similarity	NPD6777	Approved
0.8085	Intermediate Similarity	NPD6781	Approved
0.8085	Intermediate Similarity	NPD6778	Approved
0.8085	Intermediate Similarity	NPD6779	Approved
0.8073	Intermediate Similarity	NPD7701	Phase 2
0.8053	Intermediate Similarity	NPD7435	Discontinued
0.8045	Intermediate Similarity	NPD6797	Phase 2
0.8035	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.801	Intermediate Similarity	NPD7871	Phase 2
0.801	Intermediate Similarity	NPD7870	Phase 2
0.8	Intermediate Similarity	NPD6823	Phase 2
0.7979	Intermediate Similarity	NPD7700	Phase 2
0.7979	Intermediate Similarity	NPD7699	Phase 2
0.7965	Intermediate Similarity	NPD8455	Phase 2
0.7898	Intermediate Similarity	NPD6959	Discontinued
0.7897	Intermediate Similarity	NPD7874	Approved
0.7897	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD8150	Discontinued
0.7857	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7801	Approved
0.7846	Intermediate Similarity	NPD8151	Discontinued
0.7836	Intermediate Similarity	NPD3226	Approved
0.7819	Intermediate Similarity	NPD6534	Approved
0.7819	Intermediate Similarity	NPD6535	Approved
0.7778	Intermediate Similarity	NPD3818	Discontinued
0.7766	Intermediate Similarity	NPD6213	Phase 3
0.7766	Intermediate Similarity	NPD6212	Phase 3
0.7766	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7819	Suspended
0.7732	Intermediate Similarity	NPD8320	Phase 1
0.7732	Intermediate Similarity	NPD8319	Approved
0.7714	Intermediate Similarity	NPD5402	Approved
0.7711	Intermediate Similarity	NPD2346	Discontinued
0.7688	Intermediate Similarity	NPD4380	Phase 2
0.768	Intermediate Similarity	NPD3751	Discontinued
0.7667	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6166	Phase 2
0.7667	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD5844	Phase 1
0.7627	Intermediate Similarity	NPD7075	Discontinued
0.7624	Intermediate Similarity	NPD7473	Discontinued
0.7614	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7228	Approved
0.7556	Intermediate Similarity	NPD6232	Discontinued
0.7542	Intermediate Similarity	NPD5494	Approved
0.7512	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD1934	Approved
0.7459	Intermediate Similarity	NPD3787	Discontinued
0.7458	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD2801	Approved
0.7429	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD2935	Discontinued
0.7333	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8059	Phase 3
0.733	Intermediate Similarity	NPD7458	Discontinued
0.7326	Intermediate Similarity	NPD7240	Approved
0.7314	Intermediate Similarity	NPD5403	Approved
0.731	Intermediate Similarity	NPD6674	Discontinued
0.7303	Intermediate Similarity	NPD6801	Discontinued
0.7299	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7768	Phase 2
0.7278	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4628	Phase 3
0.725	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7411	Suspended
0.7234	Intermediate Similarity	NPD7685	Pre-registration
0.7207	Intermediate Similarity	NPD6844	Discontinued
0.7207	Intermediate Similarity	NPD37	Approved
0.72	Intermediate Similarity	NPD2534	Approved
0.72	Intermediate Similarity	NPD2532	Approved
0.72	Intermediate Similarity	NPD5401	Approved
0.72	Intermediate Similarity	NPD2533	Approved
0.7198	Intermediate Similarity	NPD6234	Discontinued
0.7193	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4966	Approved
0.7182	Intermediate Similarity	NPD4967	Phase 2
0.7182	Intermediate Similarity	NPD4965	Approved
0.7168	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD3750	Approved
0.7151	Intermediate Similarity	NPD1549	Phase 2
0.7127	Intermediate Similarity	NPD3817	Phase 2
0.7126	Intermediate Similarity	NPD2313	Discontinued
0.7121	Intermediate Similarity	NPD8285	Discontinued
0.7102	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6599	Discontinued
0.7093	Intermediate Similarity	NPD7266	Discontinued
0.7088	Intermediate Similarity	NPD3882	Suspended
0.7076	Intermediate Similarity	NPD2799	Discontinued
0.7072	Intermediate Similarity	NPD1465	Phase 2
0.7069	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1511	Approved
0.7044	Intermediate Similarity	NPD7584	Approved
0.7035	Intermediate Similarity	NPD1551	Phase 2
0.703	Intermediate Similarity	NPD1470	Approved
0.7024	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7985	Registered
0.7011	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2798	Approved
0.6983	Remote Similarity	NPD1653	Approved
0.6971	Remote Similarity	NPD7930	Approved
0.6966	Remote Similarity	NPD1512	Approved
0.6957	Remote Similarity	NPD3749	Approved
0.6949	Remote Similarity	NPD7390	Discontinued
0.6949	Remote Similarity	NPD6799	Approved
0.6936	Remote Similarity	NPD6099	Approved
0.6936	Remote Similarity	NPD6100	Approved
0.6936	Remote Similarity	NPD2796	Approved
0.6935	Remote Similarity	NPD7199	Phase 2
0.6919	Remote Similarity	NPD7097	Phase 1
0.6905	Remote Similarity	NPD6832	Phase 2
0.6901	Remote Similarity	NPD1933	Approved
0.6897	Remote Similarity	NPD7680	Approved
0.689	Remote Similarity	NPD1201	Approved
0.689	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1091	Approved
0.6879	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3748	Approved
0.6879	Remote Similarity	NPD1510	Phase 2
0.6875	Remote Similarity	NPD7003	Approved
0.6872	Remote Similarity	NPD6273	Approved
0.6869	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4625	Phase 3
0.686	Remote Similarity	NPD1607	Approved
0.6857	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD8127	Discontinued
0.6842	Remote Similarity	NPD4060	Phase 1
0.6842	Remote Similarity	NPD7177	Discontinued
0.6839	Remote Similarity	NPD5405	Approved
0.6839	Remote Similarity	NPD5404	Approved
0.6839	Remote Similarity	NPD5406	Approved
0.6839	Remote Similarity	NPD5408	Approved
0.6829	Remote Similarity	NPD7999	Approved
0.6818	Remote Similarity	NPD2800	Approved
0.6809	Remote Similarity	NPD5711	Approved
0.6809	Remote Similarity	NPD5710	Approved
0.6802	Remote Similarity	NPD447	Suspended
0.68	Remote Similarity	NPD5763	Approved
0.68	Remote Similarity	NPD5762	Approved
0.68	Remote Similarity	NPD2344	Approved
0.68	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3300	Phase 2
0.6782	Remote Similarity	NPD7033	Discontinued
0.678	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7799	Discontinued
0.6754	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2861	Phase 2
0.6745	Remote Similarity	NPD8404	Phase 2
0.6744	Remote Similarity	NPD1240	Approved
0.6743	Remote Similarity	NPD2438	Suspended
0.6736	Remote Similarity	NPD5953	Discontinued
0.6726	Remote Similarity	NPD1203	Approved
0.6725	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6355	Discontinued
0.6686	Remote Similarity	NPD6233	Phase 2
0.6686	Remote Similarity	NPD4308	Phase 3
0.6685	Remote Similarity	NPD8166	Discontinued
0.6683	Remote Similarity	NPD7585	Approved
0.6667	Remote Similarity	NPD2424	Discontinued
0.6667	Remote Similarity	NPD1247	Approved
0.6667	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2651	Approved
0.6667	Remote Similarity	NPD6696	Suspended
0.6667	Remote Similarity	NPD5125	Phase 3
0.6667	Remote Similarity	NPD2649	Approved
0.6667	Remote Similarity	NPD5126	Approved
0.6667	Remote Similarity	NPD8651	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