NPASS Compound

Structure

NPC128582 OpenBabel07101719512D 46 55 0 0 1 0 0 0 0 0999 V2000 -8.3150 3.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8573 1.4576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8497 4.4955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7225 1.2434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8497 5.4435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8708 0.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6707 4.0215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8374 1.5831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6707 5.9175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1340 -0.2895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9505 3.4356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4941 1.8051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9680 5.4975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7402 -0.0620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4917 4.4955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1007 0.9865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4917 5.4435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2490 0.0502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9505 4.9695 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7340 0.2902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6730 3.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2356 1.7145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6730 5.1505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0610 -0.1581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3932 4.2025 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1644 1.1348 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8520 3.7286 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6494 1.3748 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4940 4.6765 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8240 0.1816 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3932 5.7364 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4044 -0.3802 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.4940 3.7286 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9723 1.1179 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.8520 4.6765 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7977 0.4385 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.9160 5.4975 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4092 0.6096 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6730 2.3066 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3839 2.6508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6730 6.0985 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2093 -1.0944 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6730 3.2546 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.6557 0.5310 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -7.4940 3.7286 0.0000 S 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 33 1 0 0 0 0 2 34 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 15 2 0 0 0 0 8 16 2 0 0 0 0 9 17 2 0 0 0 0 10 18 2 0 0 0 0 11 27 1 0 0 0 0 13 29 1 0 0 0 0 13 37 1 0 0 0 0 14 38 1 0 0 0 0 15 17 1 0 0 0 0 15 25 1 0 0 0 0 16 18 1 0 0 0 0 16 26 1 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 19 25 1 1 0 0 0 19 31 1 0 0 0 0 19 35 1 0 0 0 0 20 26 1 1 0 0 0 20 32 1 0 0 0 0 20 36 1 0 0 0 0 21 33 1 0 0 0 0 21 39 2 0 0 0 0 22 28 1 0 0 0 0 22 34 1 0 0 0 0 22 40 2 0 0 0 0 23 29 1 0 0 0 0 23 35 1 0 0 0 0 23 41 2 0 0 0 0 24 30 1 0 0 0 0 24 36 1 0 0 0 0 24 42 2 0 0 0 0 25 11 1 1 0 0 0 25 26 1 0 0 0 0 26 12 1 1 0 0 0 27 21 1 6 0 0 0 27 35 1 0 0 0 0 27 43 1 0 0 0 0 28 12 1 1 0 0 0 28 36 1 0 0 0 0 28 44 1 0 0 0 0 29 33 1 0 0 0 0 29 45 1 1 0 0 0 30 14 1 1 0 0 0 30 34 1 0 0 0 0 30 46 1 0 0 0 0 43 45 1 0 0 0 0 44 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	696.1
Volume:	608.265
LogP:	3.007
LogD:	1.907
LogS:	-4.375
# Rotatable Bonds:	3
TPSA:	145.76
# H-Bond Aceptor:	12
# H-Bond Donor:	4
# Rings:	12
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.344
Synthetic Accessibility Score:	7.701
Fsp3:	0.467
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:	-5.631
MDCK Permeability:	1.2037171472911723e-05
Pgp-inhibitor:	0.7
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.276
20% Bioavailability (F20%):	0.937
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.073
Plasma Protein Binding (PPB):	82.43587493896484%
Volume Distribution (VD):	1.145
Pgp-substrate:	4.088703632354736%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.174
CYP2C19-inhibitor:	0.975
CYP2C19-substrate:	0.942
CYP2C9-inhibitor:	0.982
CYP2C9-substrate:	0.118
CYP2D6-inhibitor:	0.132
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.963
CYP3A4-substrate:	0.992

ADMET: Excretion

Clearance (CL):	7.122
Half-life (T1/2):	0.006

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.812
Drug-inuced Liver Injury (DILI):	0.996
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.9
Maximum Recommended Daily Dose:	0.295
Skin Sensitization:	0.918
Carcinogencity:	0.305
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.001

Download Data

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

Natural Product: NPC128582

Natural Product ID:	NPC128582
*Common Name:**	Chaetocin
IUPAC Name:	n.a.
Synonyms:	(+)-Chaetocin; Chaetocin
Standard InCHIKey:	PZPPOCZWRGNKIR-PNVYSBBASA-N
Standard InCHI:	InChI=1S/C30H28N6O6S4/c1-33-21(39)27-11-25(15-7-3-5-9-17(15)31-19(25)35(27)23(41)29(33,13-37)45-43-27)26-12-28-22(40)34(2)30(14-38,46-44-28)24(42)36(28)20(26)32-18-10-6-4-8-16(18)26/h3-10,19-20,31-32,37-38H,11-14H2,1-2H3/t19-,20-,25+,26+,27+,28+,29+,30+/m1/s1
SMILES:	CN1C(=O)[C@@]23C[C@@]4(c5ccccc5N[C@@H]4N2C(=O)[C@]1(CO)SS3)[C@@]12C[C@]34C(=O)N(C)[C@](CO)(C(=O)N3[C@H]2Nc2ccccc12)SS4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1089316
PubChem CID:	11657687
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001733] Pyrroloindoles

*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
NPO333	Nectria inventa	Species	Nectriaceae	Eukaryota	n.a.	isolated from sediment collected by dredge at >600 m in the Monterey Bay trench	n.a.	PMID[20303767]
NPO333	Nectria inventa	Species	Nectriaceae	Eukaryota	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	45
Others	8

Activity Type	# Activity
Cell Line	2
CELL-LINE	1
Individual Protein	30
NON-MOLECULAR	4
Organism	2
Others	12
PROTEIN COMPLEX	4
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT470	Individual Protein	Rhodesain	Trypanosoma brucei rhodesiense	IC50	>	50000.0	nM	PMID[482999]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	<	600.0	nM	PMID[482999]
NPT81	Cell Line	A549	Homo sapiens	IC50	<	25.0	nM	PMID[482999]
NPT6255	Individual Protein	Thioredoxin reductase 1	Homo sapiens	IC50	=	4600.0	nM	PMID[482999]
NPT6434	Individual Protein	Histone-lysine N-methyltransferase Su(var)3-9	Drosophila melanogaster	IC50	=	600.0	nM	PMID[483000]
NPT6404	Individual Protein	Histone-lysine N-methyltransferase EHMT2	Mus musculus	IC50	=	2500.0	nM	PMID[483000]
NPT6435	Individual Protein	Histone-lysine N-methyltransferase E(z)	Drosophila melanogaster	IC50	>	90000.0	nM	PMID[483000]
NPT6557	Individual Protein	Histone-lysine N-methyltransferase pr-set7	Drosophila melanogaster	IC50	>	180000.0	nM	PMID[483000]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	IC50	=	2400.0	nM	PMID[483003]
NPT6557	Individual Protein	Histone-lysine N-methyltransferase pr-set7	Drosophila melanogaster	IC50	>	90000.0	nM	PMID[483003]
NPT6435	Individual Protein	Histone-lysine N-methyltransferase E(z)	Drosophila melanogaster	IC50	>	90000.0	nM	PMID[483003]
NPT6404	Individual Protein	Histone-lysine N-methyltransferase EHMT2	Mus musculus	IC50	=	2500.0	nM	PMID[483003]
NPT5635	Individual Protein	Histone-lysine N-methyltransferase SUV39H1	Homo sapiens	IC50	=	800.0	nM	PMID[483003]
NPT6434	Individual Protein	Histone-lysine N-methyltransferase Su(var)3-9	Drosophila melanogaster	IC50	=	600.0	nM	PMID[483003]
NPT211	Individual Protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	IC50	=	100.0	nM	PMID[483004]
NPT211	Individual Protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	IC50	=	40.0	nM	PMID[483004]
NPT211	Individual Protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	IC50	=	12500.0	nM	PMID[483004]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	IC50	=	2400.0	nM	PMID[483005]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	IC50	=	7200.0	nM	PMID[483005]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Inhibition	=	8.0	%	PMID[483006]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	IC50	=	2570.4	nM	PMID[483006]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	IC50	=	2600.0	nM	PMID[483006]
NPT6404	Individual Protein	Histone-lysine N-methyltransferase EHMT2	Mus musculus	IC50	=	2500.0	nM	PMID[483006]
NPT5635	Individual Protein	Histone-lysine N-methyltransferase SUV39H1	Homo sapiens	IC50	=	800.0	nM	PMID[483006]
NPT6434	Individual Protein	Histone-lysine N-methyltransferase Su(var)3-9	Drosophila melanogaster	IC50	=	600.0	nM	PMID[483006]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	IC50	=	2500.0	nM	PMID[483007]
NPT6434	Individual Protein	Histone-lysine N-methyltransferase Su(var)3-9	Drosophila melanogaster	IC50	=	800.0	nM	PMID[483007]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	IC50	=	2500.0	nM	PMID[483008]
NPT5635	Individual Protein	Histone-lysine N-methyltransferase SUV39H1	Homo sapiens	IC50	=	800.0	nM	PMID[483008]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	IC50	=	2500.0	nM	PMID[483009]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	IC50	=	2500.0	nM	PMID[483013]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	IC50	=	2500.0	nM	PMID[483014]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	2.0	nM	PMID[482999]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[482999]
NPT2	Others	Unspecified		IC50	=	600.0	nM	PMID[482999]
NPT2	Others	Unspecified		IC50	=	800.0	nM	PMID[483000]
NPT25732	SINGLE PROTEIN	Histone-lysine N-methyltransferase, H3 lysine-9 specific dim-5 (EC 2.1.1.43) (Histone H3-K9 methyltransferase dim-5) (H3-K9-HMTase dim-5) (HKMT)	Neurospora crassa	IC50	=	3000.0	nM	PMID[483000]
NPT2	Others	Unspecified		IC50	>	180000.0	nM	PMID[483000]
NPT2	Others	Unspecified		IC50	=	600.0	nM	PMID[483001]
NPT2	Others	Unspecified		IC50	>	90000.0	nM	PMID[483003]
NPT2	Others	Unspecified		IC50	=	3000.0	nM	PMID[483003]
NPT2	Others	Unspecified		IC50	=	3000.0	nM	PMID[483006]
NPT2	Others	Unspecified		IC50	=	3000.0	nM	PMID[483008]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Survival	=	-3.25	%	PMID[483010]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Survival	=	67.8	%	PMID[483010]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Survival	=	-2.63	%	PMID[483010]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Survival	=	-4.22	%	PMID[483010]
NPT2	Others	Unspecified		Activity	=	11.0	%	PMID[483011]
NPT2	Others	Unspecified		CC50	=	3.5	nM	PMID[483011]
NPT1116	Organism	Feline immunodeficiency virus	Feline immunodeficiency virus	EC50	=	1.7	nM	PMID[483011]
NPT27	Others	Unspecified		Ratio CC50/EC50	=	2.1	n.a.	PMID[483011]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	IC50	=	100.0	nM	PMID[483012]
NPT25738	PROTEIN COMPLEX	Histone acetyltransferase p300/Hypoxia-inducible factor 1-alpha	Homo sapiens	IC50	=	12500.0	nM	PMID[483012]
NPT25738	PROTEIN COMPLEX	Histone acetyltransferase p300/Hypoxia-inducible factor 1-alpha	Homo sapiens	IC50	=	12500.0	nM	PMID[483015]

☑ 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 NPC128582 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	280
0.1-0.2	1872
0.2-0.3	11290
0.3-0.4	22065
0.4-0.5	4952
0.5-0.6	1961
0.6-0.7	217
0.7-0.8	33
0.8-0.85	8
0.85-0.9	6
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC477179
0.9282	High Similarity	NPC477180
0.9282	High Similarity	NPC254850
0.9282	High Similarity	NPC477178
0.9282	High Similarity	NPC477181
0.9231	High Similarity	NPC470490
0.913	High Similarity	NPC475259
0.913	High Similarity	NPC471950
0.913	High Similarity	NPC471945
0.9032	High Similarity	NPC475359
0.9032	High Similarity	NPC191817
0.9022	High Similarity	NPC477173
0.9022	High Similarity	NPC477174
0.8973	High Similarity	NPC470488
0.8877	High Similarity	NPC471946
0.8877	High Similarity	NPC471951
0.8624	High Similarity	NPC470491
0.8457	Intermediate Similarity	NPC242269
0.8368	Intermediate Similarity	NPC470489
0.8363	Intermediate Similarity	NPC276085
0.8069	Intermediate Similarity	NPC312942
0.8069	Intermediate Similarity	NPC327095
0.7989	Intermediate Similarity	NPC222029
0.7861	Intermediate Similarity	NPC470731
0.7854	Intermediate Similarity	NPC40455
0.7703	Intermediate Similarity	NPC297862
0.7692	Intermediate Similarity	NPC470301
0.766	Intermediate Similarity	NPC307396
0.7644	Intermediate Similarity	NPC276430
0.7598	Intermediate Similarity	NPC470732
0.756	Intermediate Similarity	NPC19170
0.75	Intermediate Similarity	NPC66936
0.7465	Intermediate Similarity	NPC475859
0.7465	Intermediate Similarity	NPC475969
0.7429	Intermediate Similarity	NPC476817
0.7418	Intermediate Similarity	NPC477175
0.7418	Intermediate Similarity	NPC470730
0.7377	Intermediate Similarity	NPC471124
0.7353	Intermediate Similarity	NPC471123
0.7349	Intermediate Similarity	NPC165743
0.7288	Intermediate Similarity	NPC109787
0.7264	Intermediate Similarity	NPC471436
0.7253	Intermediate Similarity	NPC471122
0.7222	Intermediate Similarity	NPC477177
0.7222	Intermediate Similarity	NPC474877
0.7217	Intermediate Similarity	NPC253987
0.7181	Intermediate Similarity	NPC285622
0.7176	Intermediate Similarity	NPC470729
0.7176	Intermediate Similarity	NPC477176
0.7168	Intermediate Similarity	NPC469560
0.7156	Intermediate Similarity	NPC63279
0.7151	Intermediate Similarity	NPC473329
0.7123	Intermediate Similarity	NPC297642
0.712	Intermediate Similarity	NPC68650
0.7083	Intermediate Similarity	NPC286994
0.7083	Intermediate Similarity	NPC145754
0.7026	Intermediate Similarity	NPC259626
0.7024	Intermediate Similarity	NPC252794
0.6974	Remote Similarity	NPC2933
0.6935	Remote Similarity	NPC472102
0.6935	Remote Similarity	NPC309531
0.6931	Remote Similarity	NPC475248
0.6931	Remote Similarity	NPC63047
0.6923	Remote Similarity	NPC256288
0.6863	Remote Similarity	NPC106118
0.6862	Remote Similarity	NPC328270
0.686	Remote Similarity	NPC329833
0.6847	Remote Similarity	NPC471199
0.6847	Remote Similarity	NPC162440
0.6825	Remote Similarity	NPC472106
0.6818	Remote Similarity	NPC473615
0.6798	Remote Similarity	NPC472540
0.6798	Remote Similarity	NPC470787
0.6798	Remote Similarity	NPC472539
0.6788	Remote Similarity	NPC470548
0.6784	Remote Similarity	NPC229484
0.6765	Remote Similarity	NPC472542
0.6765	Remote Similarity	NPC472541
0.675	Remote Similarity	NPC292675
0.6738	Remote Similarity	NPC104345
0.6736	Remote Similarity	NPC473880
0.6728	Remote Similarity	NPC272174
0.672	Remote Similarity	NPC472120
0.672	Remote Similarity	NPC472101
0.672	Remote Similarity	NPC469741
0.6719	Remote Similarity	NPC472118
0.6704	Remote Similarity	NPC186284
0.6704	Remote Similarity	NPC22082
0.6701	Remote Similarity	NPC475097
0.6682	Remote Similarity	NPC471663
0.6667	Remote Similarity	NPC225400
0.6649	Remote Similarity	NPC473743
0.6635	Remote Similarity	NPC470786
0.6635	Remote Similarity	NPC471155
0.6635	Remote Similarity	NPC472538
0.6621	Remote Similarity	NPC474896
0.6615	Remote Similarity	NPC214960
0.6615	Remote Similarity	NPC279527
0.6604	Remote Similarity	NPC270241
0.6599	Remote Similarity	NPC475094
0.6598	Remote Similarity	NPC355
0.6591	Remote Similarity	NPC31097
0.6583	Remote Similarity	NPC477159
0.6582	Remote Similarity	NPC476441
0.6564	Remote Similarity	NPC161861
0.6562	Remote Similarity	NPC475420
0.6561	Remote Similarity	NPC113946
0.6545	Remote Similarity	NPC472117
0.6528	Remote Similarity	NPC472115
0.6528	Remote Similarity	NPC472114
0.6526	Remote Similarity	NPC285192
0.6524	Remote Similarity	NPC473002
0.6522	Remote Similarity	NPC90967
0.6489	Remote Similarity	NPC478076
0.6482	Remote Similarity	NPC166169
0.648	Remote Similarity	NPC214626
0.648	Remote Similarity	NPC251212
0.648	Remote Similarity	NPC139085
0.6458	Remote Similarity	NPC286871
0.6458	Remote Similarity	NPC176983
0.644	Remote Similarity	NPC473003
0.6438	Remote Similarity	NPC471197
0.6432	Remote Similarity	NPC264589
0.6422	Remote Similarity	NPC284706
0.6419	Remote Similarity	NPC107077
0.6419	Remote Similarity	NPC223791
0.6417	Remote Similarity	NPC318086
0.6409	Remote Similarity	NPC471198
0.6402	Remote Similarity	NPC54420
0.6396	Remote Similarity	NPC177261
0.6396	Remote Similarity	NPC476425
0.6383	Remote Similarity	NPC154602
0.6374	Remote Similarity	NPC130251
0.6373	Remote Similarity	NPC99632
0.6373	Remote Similarity	NPC282339
0.6368	Remote Similarity	NPC476428
0.6355	Remote Similarity	NPC476095
0.6354	Remote Similarity	NPC36495
0.6354	Remote Similarity	NPC469902
0.6346	Remote Similarity	NPC294693
0.6343	Remote Similarity	NPC162860
0.6338	Remote Similarity	NPC295548
0.6337	Remote Similarity	NPC475915
0.6335	Remote Similarity	NPC248601
0.6335	Remote Similarity	NPC324850
0.6333	Remote Similarity	NPC52557
0.6324	Remote Similarity	NPC135601
0.6324	Remote Similarity	NPC17273
0.6324	Remote Similarity	NPC141612
0.6321	Remote Similarity	NPC225319
0.6318	Remote Similarity	NPC91179
0.6311	Remote Similarity	NPC105055
0.6311	Remote Similarity	NPC22689
0.6303	Remote Similarity	NPC14812
0.6302	Remote Similarity	NPC469898
0.6298	Remote Similarity	NPC267508
0.6289	Remote Similarity	NPC194881
0.6277	Remote Similarity	NPC478028
0.6275	Remote Similarity	NPC52262
0.6269	Remote Similarity	NPC99043
0.6269	Remote Similarity	NPC218594
0.6268	Remote Similarity	NPC221687
0.6268	Remote Similarity	NPC34717
0.6263	Remote Similarity	NPC117032
0.625	Remote Similarity	NPC29285
0.6244	Remote Similarity	NPC469904
0.6233	Remote Similarity	NPC219397
0.6232	Remote Similarity	NPC473298
0.6227	Remote Similarity	NPC473006
0.6225	Remote Similarity	NPC302235
0.6223	Remote Similarity	NPC478029
0.6219	Remote Similarity	NPC260075
0.6219	Remote Similarity	NPC473001
0.6218	Remote Similarity	NPC61013
0.6214	Remote Similarity	NPC181928
0.6211	Remote Similarity	NPC206592
0.6211	Remote Similarity	NPC475763
0.6211	Remote Similarity	NPC243756
0.6197	Remote Similarity	NPC475489
0.6196	Remote Similarity	NPC315051
0.6188	Remote Similarity	NPC477714
0.6186	Remote Similarity	NPC193410
0.6186	Remote Similarity	NPC469901
0.6185	Remote Similarity	NPC302169
0.6179	Remote Similarity	NPC171317
0.6178	Remote Similarity	NPC285381
0.6162	Remote Similarity	NPC301760
0.6154	Remote Similarity	NPC248117
0.6154	Remote Similarity	NPC301501
0.6147	Remote Similarity	NPC71238
0.6146	Remote Similarity	NPC469903
0.6143	Remote Similarity	NPC477715
0.6143	Remote Similarity	NPC244425
0.6143	Remote Similarity	NPC15384
0.6139	Remote Similarity	NPC476326
0.6139	Remote Similarity	NPC14849
0.6135	Remote Similarity	NPC17059
0.6108	Remote Similarity	NPC131450
0.6108	Remote Similarity	NPC182057
0.6108	Remote Similarity	NPC11126

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 NPC128582 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	532
0.2-0.3	882
0.3-0.4	2382
0.4-0.5	3768
0.5-0.6	1331
0.6-0.7	92
0.7-0.8	1
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
0.7644	Intermediate Similarity	NPD8240	Discontinued
0.7198	Intermediate Similarity	NPD8630	Approved
0.6798	Remote Similarity	NPD3625	Discontinued
0.6735	Remote Similarity	NPD6878	Phase 2
0.6735	Remote Similarity	NPD6879	Phase 2
0.6723	Remote Similarity	NPD6358	Phase 2
0.6722	Remote Similarity	NPD5024	Approved
0.6721	Remote Similarity	NPD5941	Approved
0.6721	Remote Similarity	NPD5942	Approved
0.6703	Remote Similarity	NPD8402	Approved
0.6703	Remote Similarity	NPD8400	Approved
0.6703	Remote Similarity	NPD8401	Approved
0.6684	Remote Similarity	NPD5774	Approved
0.6684	Remote Similarity	NPD5775	Approved
0.6633	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5918	Discontinued
0.6561	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7599	Phase 2
0.6513	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7595	Discontinued
0.6477	Remote Similarity	NPD4976	Discontinued
0.6436	Remote Similarity	NPD6557	Phase 2
0.6432	Remote Similarity	NPD3509	Approved
0.6432	Remote Similarity	NPD3510	Approved
0.6425	Remote Similarity	NPD3790	Phase 2
0.6406	Remote Similarity	NPD7600	Phase 2
0.6402	Remote Similarity	NPD8322	Phase 2
0.6395	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD5606	Discontinued
0.6364	Remote Similarity	NPD4432	Discontinued
0.6335	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD6395	Phase 2
0.6335	Remote Similarity	NPD1663	Discontinued
0.6333	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD6200	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD3989	Phase 3
0.631	Remote Similarity	NPD2426	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD8114	Approved
0.6308	Remote Similarity	NPD8115	Approved
0.6298	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD3990	Phase 3
0.6286	Remote Similarity	NPD6792	Phase 3
0.6277	Remote Similarity	NPD4682	Phase 2
0.627	Remote Similarity	NPD3508	Approved
0.6268	Remote Similarity	NPD7618	Phase 3
0.6268	Remote Similarity	NPD7619	Phase 3
0.6264	Remote Similarity	NPD6294	Approved
0.6264	Remote Similarity	NPD6295	Approved
0.6263	Remote Similarity	NPD3248	Phase 1
0.6257	Remote Similarity	NPD5581	Approved
0.6257	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD7995	Phase 2
0.6244	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD5748	Phase 2
0.623	Remote Similarity	NPD4121	Phase 3
0.623	Remote Similarity	NPD4120	Approved
0.6219	Remote Similarity	NPD5840	Discontinued
0.6216	Remote Similarity	NPD6566	Discontinued
0.6214	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD5742	Approved
0.6198	Remote Similarity	NPD5743	Approved
0.6198	Remote Similarity	NPD5741	Approved
0.6182	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD5318	Discontinued
0.6169	Remote Similarity	NPD4091	Approved
0.6166	Remote Similarity	NPD7091	Discontinued
0.6162	Remote Similarity	NPD7890	Discontinued
0.6158	Remote Similarity	NPD3240	Phase 2
0.6146	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD2790	Discontinued
0.6145	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD3992	Approved
0.6139	Remote Similarity	NPD3991	Approved
0.6139	Remote Similarity	NPD3996	Approved
0.6139	Remote Similarity	NPD3994	Approved
0.6139	Remote Similarity	NPD3993	Approved
0.6139	Remote Similarity	NPD3995	Approved
0.6139	Remote Similarity	NPD4092	Approved
0.6134	Remote Similarity	NPD6019	Approved
0.6134	Remote Similarity	NPD5659	Approved
0.6134	Remote Similarity	NPD6018	Approved
0.6134	Remote Similarity	NPD5660	Approved
0.6133	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.613	Remote Similarity	NPD7824	Approved
0.6129	Remote Similarity	NPD6768	Approved
0.6126	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7970	Approved
0.6124	Remote Similarity	NPD5993	Phase 1
0.6121	Remote Similarity	NPD7791	Approved
0.6121	Remote Similarity	NPD7951	Approved
0.6121	Remote Similarity	NPD7790	Approved
0.6121	Remote Similarity	NPD7789	Approved
0.6121	Remote Similarity	NPD7950	Approved
0.6121	Remote Similarity	NPD7952	Approved
0.6121	Remote Similarity	NPD7953	Approved
0.6117	Remote Similarity	NPD5933	Phase 3
0.6117	Remote Similarity	NPD5932	Phase 3
0.6117	Remote Similarity	NPD5931	Phase 3
0.6114	Remote Similarity	NPD7072	Phase 2
0.6108	Remote Similarity	NPD3997	Approved
0.6108	Remote Similarity	NPD3998	Approved
0.6108	Remote Similarity	NPD3999	Approved
0.6105	Remote Similarity	NPD2638	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD4393	Approved
0.6103	Remote Similarity	NPD33	Approved
0.6101	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD4153	Approved
0.6095	Remote Similarity	NPD7786	Discontinued
0.6093	Remote Similarity	NPD7817	Phase 1
0.6091	Remote Similarity	NPD2288	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD4549	Discontinued
0.6089	Remote Similarity	NPD3040	Approved
0.6087	Remote Similarity	NPD4410	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7781	Approved
0.6087	Remote Similarity	NPD7780	Approved
0.6087	Remote Similarity	NPD4411	Phase 1
0.6082	Remote Similarity	NPD7105	Phase 1
0.608	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.608	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7308	Discontinued
0.6075	Remote Similarity	NPD2093	Discontinued
0.6075	Remote Similarity	NPD2010	Phase 3
0.607	Remote Similarity	NPD5997	Discontinued
0.6069	Remote Similarity	NPD5657	Phase 3
0.6068	Remote Similarity	NPD8241	Phase 2
0.6068	Remote Similarity	NPD7482	Phase 2
0.6068	Remote Similarity	NPD7483	Phase 2
0.6065	Remote Similarity	NPD7724	Phase 2
0.6059	Remote Similarity	NPD5181	Approved
0.6059	Remote Similarity	NPD5179	Approved
0.6059	Remote Similarity	NPD5180	Approved
0.6056	Remote Similarity	NPD4019	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD7254	Discontinued
0.6053	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5570	Discontinued
0.6051	Remote Similarity	NPD8060	Phase 1
0.6051	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD6694	Clinical (unspecified phase)
0.605	Remote Similarity	NPD7968	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD7578	Phase 2
0.6043	Remote Similarity	NPD7731	Approved
0.6043	Remote Similarity	NPD7730	Approved
0.604	Remote Similarity	NPD3522	Approved
0.6038	Remote Similarity	NPD4602	Approved
0.6032	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD5060	Phase 1
0.6032	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD7271	Approved
0.602	Remote Similarity	NPD7663	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7569	Approved
0.6019	Remote Similarity	NPD7570	Approved
0.6018	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD6301	Phase 2
0.6011	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD8128	Discontinued
0.6011	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.601	Remote Similarity	NPD6044	Discontinued
0.6	Remote Similarity	NPD2413	Phase 2
0.5991	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD6268	Phase 1
0.5981	Remote Similarity	NPD7683	Discontinued
0.5981	Remote Similarity	NPD7210	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7572	Phase 2
0.5979	Remote Similarity	NPD7774	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD1950	Approved
0.5978	Remote Similarity	NPD1949	Approved
0.5972	Remote Similarity	NPD5042	Phase 1
0.5972	Remote Similarity	NPD4600	Approved
0.5972	Remote Similarity	NPD4601	Approved
0.5971	Remote Similarity	NPD1966	Approved
0.5969	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.5967	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.5967	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.5967	Remote Similarity	NPD8263	Discontinued
0.5961	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.5961	Remote Similarity	NPD2461	Phase 1
0.5956	Remote Similarity	NPD3137	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD1527	Phase 2
0.5951	Remote Similarity	NPD3079	Approved
0.5951	Remote Similarity	NPD3076	Approved
0.5951	Remote Similarity	NPD3078	Approved
0.5951	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD6368	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD3077	Approved
0.5947	Remote Similarity	NPD6017	Discontinued
0.5946	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD8125	Discontinued
0.5945	Remote Similarity	NPD7727	Phase 2
0.5939	Remote Similarity	NPD4514	Approved
0.5938	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD4781	Approved
0.5934	Remote Similarity	NPD4783	Approved
0.5933	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD4706	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