NPASS Compound

Structure

CID28510 OpenBabel06191715352D 30 33 0 0 1 0 0 0 0 0999 V2000 5.0872 0.9618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2541 4.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1031 -3.6686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1213 2.9602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2123 1.4672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5025 -0.4811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6684 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5027 -1.4447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6686 -1.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5026 -1.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6692 0.9627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3369 -0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3787 2.9593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3372 0.9623 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5033 1.4440 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5036 2.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8341 -0.4814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6689 -0.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6688 -1.9264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8343 -1.4450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8344 -0.4817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6287 2.9597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8342 -1.4453 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5028 -0.4821 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 1.6290 3.9701 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -2.4453 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3790 3.9696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6690 -2.8894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7536 2.4548 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 4 30 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 17 1 0 0 0 0 8 19 2 0 0 0 0 9 10 1 0 0 0 0 9 23 1 0 0 0 0 10 25 1 0 0 0 0 11 15 1 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 16 2 0 0 0 0 13 28 1 0 0 0 0 14 5 1 6 0 0 0 14 15 1 0 0 0 0 15 16 1 6 0 0 0 16 22 1 0 0 0 0 17 20 2 0 0 0 0 17 24 1 0 0 0 0 18 21 1 0 0 0 0 18 25 1 6 0 0 0 19 20 1 0 0 0 0 19 29 1 0 0 0 0 20 23 1 0 0 0 0 21 23 1 0 0 0 0 21 24 2 0 0 0 0 22 26 2 0 0 0 0 22 30 1 0 0 0 0 23 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.22
Volume:	422.264
LogP:	2.518
LogD:	3.103
LogS:	-4.17
# Rotatable Bonds:	6
TPSA:	80.59
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.453
Synthetic Accessibility Score:	4.572
Fsp3:	0.565
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.567
MDCK Permeability:	2.5851519239949994e-05
Pgp-inhibitor:	0.1
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.425

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.946
Plasma Protein Binding (PPB):	63.68230438232422%
Volume Distribution (VD):	1.317
Pgp-substrate:	33.494110107421875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.371
CYP1A2-substrate:	0.674
CYP2C19-inhibitor:	0.478
CYP2C19-substrate:	0.929
CYP2C9-inhibitor:	0.248
CYP2C9-substrate:	0.112
CYP2D6-inhibitor:	0.875
CYP2D6-substrate:	0.851
CYP3A4-inhibitor:	0.865
CYP3A4-substrate:	0.915

ADMET: Excretion

Clearance (CL):	8.043
Half-life (T1/2):	0.196

ADMET: Toxicity

hERG Blockers:	0.893
Human Hepatotoxicity (H-HT):	0.843
Drug-inuced Liver Injury (DILI):	0.708
AMES Toxicity:	0.525
Rat Oral Acute Toxicity:	0.945
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.356
Carcinogencity:	0.966
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC28510

Natural Product ID:	NPC28510
*Common Name:**	7Alpha-Hydroxy-7H-Mitragynine
IUPAC Name:	methyl (E)-2-[(2S,3S,7aS,12bS)-3-ethyl-7a-hydroxy-8-methoxy-2,3,4,6,7,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
Synonyms:
Standard InCHIKey:	RYENLSMHLCNXJT-CYXFISRXSA-N
Standard InCHI:	InChI=1S/C23H30N2O5/c1-5-14-12-25-10-9-23(27)20-17(7-6-8-19(20)29-3)24-21(23)18(25)11-15(14)16(13-28-2)22(26)30-4/h6-8,13-15,18,27H,5,9-12H2,1-4H3/b16-13+/t14-,15+,18+,23+/m1/s1
SMILES:	CO/C=C([C@H]1C[C@@H]2N(C[C@H]1CC)CC[C@]1(C2=Nc2c1c(OC)ccc2)O)/C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL61630
PubChem CID:	44301524
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002750] Corynanthean-type alkaloids

*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
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[15635221]
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067155]
NPO2677	Paralemnalia clavata	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18247571]
NPO1569	Mitragyna speciosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517479]
NPO8554	Cryptocarya lividula	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[27032214]
NPO1569	Mitragyna speciosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1569	Mitragyna speciosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8453	Euphorbia pannonica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6163	Picris conyzoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2677	Paralemnalia clavata	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8554	Cryptocarya lividula	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1996	Penstemon gentianoides	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1569	Mitragyna speciosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4209	Knautia montana	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25675	Anthyllis onobrychoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO317	Corticium simplex	Species	Plakinidae	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	6
ED50	2
IC50	3
Ki	18
Others	48

Activity Type	# Activity
Individual Protein	51
Organism	8
Others	18

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1074	Individual Protein	Mu opioid receptor	Cavia porcellus	Ki	=	13.49	nM	PMID[568170]
NPT271	Individual Protein	Delta opioid receptor	Homo sapiens	Ki	=	154.88	nM	PMID[568170]
NPT1075	Individual Protein	Kappa opioid receptor	Cavia porcellus	Ki	=	123.03	nM	PMID[568170]
NPT1074	Individual Protein	Mu opioid receptor	Cavia porcellus	Relative affinity	=	83.3	%	PMID[568170]
NPT271	Individual Protein	Delta opioid receptor	Homo sapiens	Relative affinity	=	6.6	%	PMID[568170]
NPT1075	Individual Protein	Kappa opioid receptor	Cavia porcellus	Relative affinity	=	10.1	%	PMID[568170]
NPT1075	Individual Protein	Kappa opioid receptor	Cavia porcellus	Ki	=	123.0	nM	PMID[568171]
NPT1074	Individual Protein	Mu opioid receptor	Cavia porcellus	Ki	=	13.0	nM	PMID[568171]
NPT1075	Individual Protein	Kappa opioid receptor	Cavia porcellus	Ki	=	195.0	nM	PMID[568171]
NPT1074	Individual Protein	Mu opioid receptor	Cavia porcellus	Ki	=	9.8	nM	PMID[568171]
NPT272	Individual Protein	Kappa opioid receptor	Homo sapiens	Inhibition	=	41.0	%	PMID[568172]
NPT271	Individual Protein	Delta opioid receptor	Homo sapiens	Inhibition	=	19.6	%	PMID[568172]
NPT223	Individual Protein	Alpha-2b adrenergic receptor	Homo sapiens	Inhibition	=	-9.9	%	PMID[568172]
NPT222	Individual Protein	Alpha-2a adrenergic receptor	Homo sapiens	Inhibition	=	-6.7	%	PMID[568172]
NPT221	Individual Protein	Alpha-1d adrenergic receptor	Homo sapiens	Inhibition	=	-1.9	%	PMID[568172]
NPT1789	Individual Protein	Alpha-1b adrenergic receptor	Homo sapiens	Inhibition	=	5.9	%	PMID[568172]
NPT1788	Individual Protein	Alpha-1a adrenergic receptor	Homo sapiens	Inhibition	=	10.1	%	PMID[568172]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Inhibition	=	81.8	%	PMID[568172]
NPT5971	Individual Protein	Nociceptin receptor	Homo sapiens	Inhibition	=	-1.6	%	PMID[568172]
NPT1788	Individual Protein	Alpha-1a adrenergic receptor	Homo sapiens	Inhibition	=	3.5	%	PMID[568172]
NPT1789	Individual Protein	Alpha-1b adrenergic receptor	Homo sapiens	Inhibition	=	-4.8	%	PMID[568172]
NPT221	Individual Protein	Alpha-1d adrenergic receptor	Homo sapiens	Inhibition	=	13.5	%	PMID[568172]
NPT222	Individual Protein	Alpha-2a adrenergic receptor	Homo sapiens	Inhibition	=	-5.4	%	PMID[568172]
NPT223	Individual Protein	Alpha-2b adrenergic receptor	Homo sapiens	Inhibition	=	1.1	%	PMID[568172]
NPT271	Individual Protein	Delta opioid receptor	Homo sapiens	Inhibition	=	93.7	%	PMID[568172]
NPT272	Individual Protein	Kappa opioid receptor	Homo sapiens	Inhibition	=	97.8	%	PMID[568172]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Inhibition	=	100.7	%	PMID[568172]
NPT5971	Individual Protein	Nociceptin receptor	Homo sapiens	Inhibition	=	3.4	%	PMID[568172]
NPT271	Individual Protein	Delta opioid receptor	Homo sapiens	Ki	=	236.0	nM	PMID[568172]
NPT272	Individual Protein	Kappa opioid receptor	Homo sapiens	Ki	=	74.1	nM	PMID[568172]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Ki	=	7.16	nM	PMID[568172]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	EC50	=	7.6	nM	PMID[568172]
NPT271	Individual Protein	Delta opioid receptor	Homo sapiens	Kb	=	550.2	nM	PMID[568172]
NPT272	Individual Protein	Kappa opioid receptor	Homo sapiens	Kb	=	115.0	nM	PMID[568172]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	EC50	=	34.5	nM	PMID[568172]
NPT1075	Individual Protein	Kappa opioid receptor	Cavia porcellus	Emax	=	77.0	%	PMID[568173]
NPT1074	Individual Protein	Mu opioid receptor	Cavia porcellus	Emax	=	77.0	%	PMID[568173]
NPT1075	Individual Protein	Kappa opioid receptor	Cavia porcellus	EC50	=	53.0	nM	PMID[568173]
NPT1074	Individual Protein	Mu opioid receptor	Cavia porcellus	EC50	=	53.0	nM	PMID[568173]
NPT1075	Individual Protein	Kappa opioid receptor	Cavia porcellus	Ratio Ki	=	10.0	n.a.	PMID[568173]
NPT1074	Individual Protein	Mu opioid receptor	Cavia porcellus	Ratio Ki	=	10.0	n.a.	PMID[568173]
NPT1075	Individual Protein	Kappa opioid receptor	Cavia porcellus	Ki	>	1000.0	nM	PMID[568173]
NPT1074	Individual Protein	Mu opioid receptor	Cavia porcellus	Ki	=	7.2	nM	PMID[568173]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	IC50	=	725.0	nM	PMID[568174]
NPT1167	Individual Protein	Delta opioid receptor	Mus musculus	IC50	=	691.0	nM	PMID[568174]
NPT3603	Individual Protein	Kappa opioid receptor	Mus musculus	IC50	=	2524.0	nM	PMID[568174]
NPT1168	Individual Protein	Mu opioid receptor	Mus musculus	Emax	=	77.0	%	PMID[568174]
NPT1168	Individual Protein	Mu opioid receptor	Mus musculus	EC50	=	53.0	nM	PMID[568174]
NPT1167	Individual Protein	Delta opioid receptor	Mus musculus	Ki	=	90.0	nM	PMID[568174]
NPT3603	Individual Protein	Kappa opioid receptor	Mus musculus	Ki	=	131.0	nM	PMID[568174]
NPT1168	Individual Protein	Mu opioid receptor	Mus musculus	Ki	=	37.0	nM	PMID[568174]
NPT938	Organism	Cavia porcellus	Cavia porcellus	pD2	=	8.2	n.a.	PMID[568170]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Relative potency	=	1071.0	%	PMID[568170]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Inhibition	=	86.3	%	PMID[568170]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Inhibition	=	99.0	%	PMID[568170]
NPT4410	Others	Opioid receptor (mu and kappa)	Cavia porcellus	Ratio Ki	=	10.0	n.a.	PMID[568171]
NPT2	Others	Unspecified		Ratio Ki	>	10.0	n.a.	PMID[568171]
NPT2	Others	Unspecified		Ki	=	155.0	nM	PMID[568171]
NPT2	Others	Unspecified		Inhibition	=	1071.0	%	PMID[568171]
NPT2	Others	Unspecified		Efficacy	=	99.0	%	PMID[568171]
NPT2	Others	Unspecified		Ki	=	145.0	nM	PMID[568171]
NPT27	Others	Unspecified		ERH	=	0.02	n.a.	PMID[568172]
NPT27	Others	Unspecified		CL	=	0.4	mL.min-1.kg-1	PMID[568172]
NPT27	Others	Unspecified		CL	=	3.7	mL.min-1.kg-1	PMID[568172]
NPT27	Others	Unspecified		Fu	=	0.852	n.a.	PMID[568172]
NPT27	Others	Unspecified		Fu	=	0.1	n.a.	PMID[568172]
NPT27	Others	Unspecified		T1/2	=	2.835	hr	PMID[568172]
NPT27	Others	Unspecified		Kel	=	0.0041	/min	PMID[568172]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	ED50	=	1.91	mg.kg-1	PMID[568172]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	MPE	=	100.0	%	PMID[568172]
NPT27	Others	Unspecified		PPB	=	90.0	%	PMID[568172]
NPT2	Others	Unspecified		Emax	=	77.0	%	PMID[568173]
NPT2	Others	Unspecified		EC50	=	53.0	nM	PMID[568173]
NPT2	Others	Unspecified		Ratio Ki	=	10.0	n.a.	PMID[568173]
NPT2	Others	Unspecified		Ki	=	60.0	nM	PMID[568173]
NPT32	Organism	Mus musculus	Mus musculus	Ratio ED50	=	5.0	n.a.	PMID[568174]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	0.46	mg.kg-1	PMID[568174]

☑ 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 NPC28510 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	251
0.1-0.2	1151
0.2-0.3	4156
0.3-0.4	12218
0.4-0.5	6644
0.5-0.6	15727
0.6-0.7	2383
0.7-0.8	159
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8478	Intermediate Similarity	NPC203972
0.822	Intermediate Similarity	NPC474077
0.8	Intermediate Similarity	NPC263709
0.8	Intermediate Similarity	NPC63210
0.8	Intermediate Similarity	NPC148468
0.8	Intermediate Similarity	NPC97380
0.8	Intermediate Similarity	NPC310403
0.8	Intermediate Similarity	NPC243673
0.7943	Intermediate Similarity	NPC211525
0.7943	Intermediate Similarity	NPC153694
0.7937	Intermediate Similarity	NPC204970
0.7921	Intermediate Similarity	NPC52059
0.7921	Intermediate Similarity	NPC470069
0.7831	Intermediate Similarity	NPC174629
0.7829	Intermediate Similarity	NPC161827
0.7822	Intermediate Similarity	NPC152768
0.7822	Intermediate Similarity	NPC148183
0.7802	Intermediate Similarity	NPC276993
0.7802	Intermediate Similarity	NPC298851
0.7802	Intermediate Similarity	NPC293255
0.7802	Intermediate Similarity	NPC210415
0.7802	Intermediate Similarity	NPC21752
0.7802	Intermediate Similarity	NPC181138
0.7737	Intermediate Similarity	NPC474059
0.768	Intermediate Similarity	NPC278887
0.7647	Intermediate Similarity	NPC475962
0.7525	Intermediate Similarity	NPC232600
0.7514	Intermediate Similarity	NPC219383
0.7448	Intermediate Similarity	NPC21425
0.7441	Intermediate Similarity	NPC21638
0.7435	Intermediate Similarity	NPC473007
0.7415	Intermediate Similarity	NPC264176
0.7413	Intermediate Similarity	NPC14339
0.7402	Intermediate Similarity	NPC476651
0.7394	Intermediate Similarity	NPC9475
0.7374	Intermediate Similarity	NPC100863
0.7371	Intermediate Similarity	NPC473008
0.7353	Intermediate Similarity	NPC168250
0.7333	Intermediate Similarity	NPC22476
0.733	Intermediate Similarity	NPC472098
0.7327	Intermediate Similarity	NPC87714
0.7322	Intermediate Similarity	NPC472121
0.732	Intermediate Similarity	NPC217294
0.7316	Intermediate Similarity	NPC39822
0.7302	Intermediate Similarity	NPC127082
0.7297	Intermediate Similarity	NPC472114
0.7297	Intermediate Similarity	NPC472115
0.7296	Intermediate Similarity	NPC473004
0.7286	Intermediate Similarity	NPC37957
0.7273	Intermediate Similarity	NPC303214
0.7251	Intermediate Similarity	NPC472099
0.7249	Intermediate Similarity	NPC168153
0.7246	Intermediate Similarity	NPC127996
0.7245	Intermediate Similarity	NPC203628
0.7238	Intermediate Similarity	NPC473297
0.7225	Intermediate Similarity	NPC470002
0.7225	Intermediate Similarity	NPC470001
0.722	Intermediate Similarity	NPC205926
0.7216	Intermediate Similarity	NPC291759
0.7214	Intermediate Similarity	NPC67904
0.7202	Intermediate Similarity	NPC473105
0.7194	Intermediate Similarity	NPC473569
0.7177	Intermediate Similarity	NPC189661
0.7173	Intermediate Similarity	NPC126515
0.7173	Intermediate Similarity	NPC274002
0.7173	Intermediate Similarity	NPC472331
0.717	Intermediate Similarity	NPC128115
0.7165	Intermediate Similarity	NPC133591
0.715	Intermediate Similarity	NPC98197
0.715	Intermediate Similarity	NPC269449
0.7136	Intermediate Similarity	NPC230313
0.7128	Intermediate Similarity	NPC207033
0.7128	Intermediate Similarity	NPC38823
0.7123	Intermediate Similarity	NPC153923
0.7122	Intermediate Similarity	NPC246140
0.7122	Intermediate Similarity	NPC195787
0.7121	Intermediate Similarity	NPC206109
0.7121	Intermediate Similarity	NPC114039
0.7104	Intermediate Similarity	NPC10875
0.7104	Intermediate Similarity	NPC10730
0.7103	Intermediate Similarity	NPC250960
0.7103	Intermediate Similarity	NPC71539
0.7087	Intermediate Similarity	NPC198160
0.7081	Intermediate Similarity	NPC116178
0.7081	Intermediate Similarity	NPC119722
0.7075	Intermediate Similarity	NPC473041
0.7074	Intermediate Similarity	NPC469462
0.7065	Intermediate Similarity	NPC272706
0.7059	Intermediate Similarity	NPC473005
0.7048	Intermediate Similarity	NPC321166
0.7048	Intermediate Similarity	NPC217903
0.7042	Intermediate Similarity	NPC288110
0.7042	Intermediate Similarity	NPC108826
0.7033	Intermediate Similarity	NPC184161
0.7028	Intermediate Similarity	NPC305984
0.7021	Intermediate Similarity	NPC19555
0.7019	Intermediate Similarity	NPC477160
0.701	Intermediate Similarity	NPC472330
0.701	Intermediate Similarity	NPC472329
0.7009	Intermediate Similarity	NPC174760
0.7005	Intermediate Similarity	NPC266994
0.6996	Remote Similarity	NPC474183
0.6996	Remote Similarity	NPC470784
0.699	Remote Similarity	NPC469460
0.699	Remote Similarity	NPC475147
0.6985	Remote Similarity	NPC1820
0.6981	Remote Similarity	NPC234772
0.698	Remote Similarity	NPC472191
0.6976	Remote Similarity	NPC15987
0.6971	Remote Similarity	NPC475910
0.6971	Remote Similarity	NPC317709
0.6971	Remote Similarity	NPC329329
0.6961	Remote Similarity	NPC138830
0.6959	Remote Similarity	NPC115588
0.6957	Remote Similarity	NPC477161
0.6948	Remote Similarity	NPC126556
0.6942	Remote Similarity	NPC317572
0.6942	Remote Similarity	NPC473460
0.6941	Remote Similarity	NPC74216
0.6939	Remote Similarity	NPC320394
0.6938	Remote Similarity	NPC469589
0.6935	Remote Similarity	NPC291359
0.6935	Remote Similarity	NPC5630
0.693	Remote Similarity	NPC10653
0.693	Remote Similarity	NPC318525
0.6923	Remote Similarity	NPC478075
0.692	Remote Similarity	NPC470785
0.692	Remote Similarity	NPC151171
0.6915	Remote Similarity	NPC204867
0.6908	Remote Similarity	NPC268077
0.6901	Remote Similarity	NPC330009
0.6898	Remote Similarity	NPC128476
0.6898	Remote Similarity	NPC474058
0.6893	Remote Similarity	NPC1464
0.6884	Remote Similarity	NPC477186
0.6881	Remote Similarity	NPC243626
0.6878	Remote Similarity	NPC299582
0.6875	Remote Similarity	NPC166667
0.6875	Remote Similarity	NPC472111
0.6875	Remote Similarity	NPC184680
0.6872	Remote Similarity	NPC87413
0.6869	Remote Similarity	NPC169402
0.6866	Remote Similarity	NPC226708
0.6866	Remote Similarity	NPC148124
0.6864	Remote Similarity	NPC311906
0.6863	Remote Similarity	NPC234933
0.6863	Remote Similarity	NPC265642
0.6863	Remote Similarity	NPC132874
0.6863	Remote Similarity	NPC138615
0.6863	Remote Similarity	NPC218733
0.686	Remote Similarity	NPC207971
0.6857	Remote Similarity	NPC475133
0.6851	Remote Similarity	NPC472100
0.6847	Remote Similarity	NPC475720
0.6847	Remote Similarity	NPC474192
0.6842	Remote Similarity	NPC212123
0.6842	Remote Similarity	NPC53344
0.684	Remote Similarity	NPC159815
0.6837	Remote Similarity	NPC96321
0.6837	Remote Similarity	NPC77777
0.6837	Remote Similarity	NPC303658
0.6837	Remote Similarity	NPC469594
0.682	Remote Similarity	NPC329830
0.682	Remote Similarity	NPC99724
0.682	Remote Similarity	NPC60621
0.6818	Remote Similarity	NPC248903
0.6818	Remote Similarity	NPC473458
0.6809	Remote Similarity	NPC284685
0.6808	Remote Similarity	NPC471080
0.6808	Remote Similarity	NPC469592
0.6804	Remote Similarity	NPC19175
0.6804	Remote Similarity	NPC473449
0.6796	Remote Similarity	NPC127178
0.6792	Remote Similarity	NPC295479
0.6792	Remote Similarity	NPC82541
0.6792	Remote Similarity	NPC220241
0.6786	Remote Similarity	NPC70092
0.6786	Remote Similarity	NPC241704
0.678	Remote Similarity	NPC17677
0.678	Remote Similarity	NPC71124
0.6777	Remote Similarity	NPC471561
0.6776	Remote Similarity	NPC316297
0.6776	Remote Similarity	NPC116238
0.6776	Remote Similarity	NPC66191
0.6776	Remote Similarity	NPC314817
0.6774	Remote Similarity	NPC150239
0.6773	Remote Similarity	NPC26928
0.6773	Remote Similarity	NPC476436
0.6772	Remote Similarity	NPC476231
0.6771	Remote Similarity	NPC257354
0.6769	Remote Similarity	NPC81939
0.6768	Remote Similarity	NPC62069
0.6766	Remote Similarity	NPC166979
0.6763	Remote Similarity	NPC469732
0.6761	Remote Similarity	NPC470481
0.6761	Remote Similarity	NPC470482
0.6757	Remote Similarity	NPC470821
0.6755	Remote Similarity	NPC476443
0.6755	Remote Similarity	NPC133817
0.6751	Remote Similarity	NPC28368

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 NPC28510 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	517
0.2-0.3	741
0.3-0.4	1403
0.4-0.5	2313
0.5-0.6	3031
0.6-0.7	955
0.7-0.8	33
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
0.7784	Intermediate Similarity	NPD6874	Approved
0.75	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD2246	Approved
0.7326	Intermediate Similarity	NPD2248	Approved
0.7291	Intermediate Similarity	NPD6905	Phase 2
0.7253	Intermediate Similarity	NPD3812	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD3437	Discontinued
0.7238	Intermediate Similarity	NPD5617	Suspended
0.7211	Intermediate Similarity	NPD3965	Phase 1
0.7206	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4539	Phase 1
0.715	Intermediate Similarity	NPD3912	Discontinued
0.7143	Intermediate Similarity	NPD5620	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2167	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2168	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD3793	Phase 3
0.71	Intermediate Similarity	NPD8249	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD5811	Approved
0.7074	Intermediate Similarity	NPD4986	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD2166	Phase 3
0.7059	Intermediate Similarity	NPD5848	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1717	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5488	Discontinued
0.703	Intermediate Similarity	NPD4668	Phase 2
0.7027	Intermediate Similarity	NPD6060	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2215	Approved
0.7	Intermediate Similarity	NPD5984	Phase 2
0.7	Intermediate Similarity	NPD2216	Approved
0.699	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD2821	Approved
0.698	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4012	Approved
0.6963	Remote Similarity	NPD5496	Approved
0.695	Remote Similarity	NPD4740	Approved
0.6947	Remote Similarity	NPD5183	Approved
0.6947	Remote Similarity	NPD5186	Approved
0.6939	Remote Similarity	NPD7546	Discontinued
0.6935	Remote Similarity	NPD2845	Phase 2
0.6935	Remote Similarity	NPD2843	Phase 2
0.6934	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5512	Phase 3
0.6923	Remote Similarity	NPD6296	Discontinued
0.6919	Remote Similarity	NPD3065	Discontinued
0.6919	Remote Similarity	NPD3119	Phase 1
0.6919	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2366	Approved
0.6919	Remote Similarity	NPD3120	Approved
0.6915	Remote Similarity	NPD955	Approved
0.6907	Remote Similarity	NPD1716	Phase 3
0.6898	Remote Similarity	NPD5967	Approved
0.6895	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5519	Discontinued
0.6881	Remote Similarity	NPD4771	Phase 2
0.6878	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD3153	Approved
0.6869	Remote Similarity	NPD3154	Approved
0.6869	Remote Similarity	NPD5565	Discontinued
0.6865	Remote Similarity	NPD6502	Phase 2
0.6865	Remote Similarity	NPD3296	Phase 1
0.686	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7608	Discontinued
0.6856	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD5312	Approved
0.6856	Remote Similarity	NPD5313	Approved
0.685	Remote Similarity	NPD5928	Phase 1
0.6845	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.684	Remote Similarity	NPD7069	Discontinued
0.6827	Remote Similarity	NPD1294	Discontinued
0.6825	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5557	Phase 1
0.6821	Remote Similarity	NPD7479	Phase 2
0.682	Remote Similarity	NPD7556	Discontinued
0.6816	Remote Similarity	NPD4373	Phase 2
0.6814	Remote Similarity	NPD4605	Approved
0.6814	Remote Similarity	NPD4604	Approved
0.6814	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.681	Remote Similarity	NPD8027	Approved
0.681	Remote Similarity	NPD2916	Discontinued
0.681	Remote Similarity	NPD4082	Approved
0.6809	Remote Similarity	NPD7955	Approved
0.6809	Remote Similarity	NPD7956	Approved
0.6806	Remote Similarity	NPD2680	Approved
0.6806	Remote Similarity	NPD2681	Approved
0.6804	Remote Similarity	NPD3909	Discontinued
0.68	Remote Similarity	NPD2792	Approved
0.6792	Remote Similarity	NPD683	Approved
0.6792	Remote Similarity	NPD1945	Phase 1
0.6784	Remote Similarity	NPD7417	Discontinued
0.6773	Remote Similarity	NPD7426	Phase 1
0.6763	Remote Similarity	NPD3416	Discontinued
0.676	Remote Similarity	NPD3656	Approved
0.6757	Remote Similarity	NPD4952	Phase 3
0.6754	Remote Similarity	NPD3251	Approved
0.6751	Remote Similarity	NPD3037	Phase 1
0.675	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD5860	Discontinued
0.6737	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5871	Discontinued
0.6732	Remote Similarity	NPD5650	Approved
0.6732	Remote Similarity	NPD5651	Approved
0.6732	Remote Similarity	NPD5652	Approved
0.6731	Remote Similarity	NPD956	Clinical (unspecified phase)
0.673	Remote Similarity	NPD2907	Approved
0.673	Remote Similarity	NPD2906	Approved
0.6722	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7318	Phase 3
0.6716	Remote Similarity	NPD4113	Discontinued
0.6703	Remote Similarity	NPD3641	Approved
0.6703	Remote Similarity	NPD3640	Phase 3
0.6703	Remote Similarity	NPD3639	Approved
0.6701	Remote Similarity	NPD2169	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5937	Approved
0.6699	Remote Similarity	NPD3802	Phase 3
0.6698	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6747	Phase 1
0.6683	Remote Similarity	NPD5548	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6321	Discontinued
0.6682	Remote Similarity	NPD7542	Phase 3
0.6682	Remote Similarity	NPD5632	Approved
0.6682	Remote Similarity	NPD7395	Discontinued
0.6682	Remote Similarity	NPD6199	Discontinued
0.6667	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4203	Approved
0.6667	Remote Similarity	NPD4204	Approved
0.6667	Remote Similarity	NPD4003	Phase 3
0.6667	Remote Similarity	NPD6744	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3446	Phase 1
0.6667	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3298	Approved
0.6667	Remote Similarity	NPD7803	Approved
0.6667	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3259	Approved
0.6667	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD3925	Approved
0.665	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6045	Phase 3
0.665	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD2672	Discontinued
0.6649	Remote Similarity	NPD3453	Discontinued
0.6648	Remote Similarity	NPD3170	Approved
0.6638	Remote Similarity	NPD6790	Phase 1
0.6636	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4493	Discontinued
0.6636	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD8161	Suspended
0.6634	Remote Similarity	NPD4523	Approved
0.6634	Remote Similarity	NPD1898	Discontinued
0.6634	Remote Similarity	NPD8025	Phase 2
0.6634	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD1381	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6063	Approved
0.6632	Remote Similarity	NPD6107	Approved
0.6632	Remote Similarity	NPD6457	Approved
0.6631	Remote Similarity	NPD6357	Discontinued
0.663	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD7797	Approved
0.6622	Remote Similarity	NPD7796	Approved
0.6616	Remote Similarity	NPD3823	Discontinued
0.6616	Remote Similarity	NPD5445	Approved
0.6615	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD7317	Phase 3
0.6613	Remote Similarity	NPD7427	Discontinued
0.6612	Remote Similarity	NPD3692	Discontinued
0.6609	Remote Similarity	NPD6716	Phase 1
0.6604	Remote Similarity	NPD5429	Discontinued
0.6603	Remote Similarity	NPD6604	Discontinued
0.6603	Remote Similarity	NPD6238	Discontinued
0.66	Remote Similarity	NPD7877	Suspended
0.66	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD2592	Discontinued
0.6594	Remote Similarity	NPD7560	Approved
0.6591	Remote Similarity	NPD7805	Phase 3
0.6588	Remote Similarity	NPD6644	Discontinued
0.6588	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7565	Approved
0.6587	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4590	Approved
0.6585	Remote Similarity	NPD5610	Approved
0.6585	Remote Similarity	NPD4591	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD8363	Approved
0.6584	Remote Similarity	NPD8364	Approved
0.6583	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD4443	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5482	Discontinued
0.658	Remote Similarity	NPD1414	Approved
0.658	Remote Similarity	NPD1411	Approved
0.658	Remote Similarity	NPD1413	Approved
0.658	Remote Similarity	NPD6746	Phase 2
0.6579	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD6962	Phase 2
0.6576	Remote Similarity	NPD6667	Approved
0.6576	Remote Similarity	NPD6666	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