NPASS Compound

Structure

CID99078 OpenBabel06191715442D 27 29 0 0 0 0 0 0 0 0999 V2000 7.0132 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2094 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4773 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3434 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0754 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3434 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3434 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0754 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2094 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2094 -1.1910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 13.0754 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 13 2 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 23 1 0 0 0 0 14 15 2 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 24 1 0 0 0 0 17 24 1 0 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 19 26 1 0 0 0 0 19 27 1 0 0 0 0 21 22 2 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 23 24 1 0 0 0 0 23 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	369.23
Volume:	402.243
LogP:	5.457
LogD:	4.149
LogS:	-5.811
# Rotatable Bonds:	10
TPSA:	38.77
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.436
Synthetic Accessibility Score:	2.459
Fsp3:	0.522
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.864
MDCK Permeability:	2.8915907023474574e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.97
30% Bioavailability (F30%):	0.54

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.22
Plasma Protein Binding (PPB):	98.12914276123047%
Volume Distribution (VD):	1.171
Pgp-substrate:	1.2738960981369019%

ADMET: Metabolism

CYP1A2-inhibitor:	0.916
CYP1A2-substrate:	0.23
CYP2C19-inhibitor:	0.872
CYP2C19-substrate:	0.204
CYP2C9-inhibitor:	0.528
CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	0.943
CYP2D6-substrate:	0.902
CYP3A4-inhibitor:	0.964
CYP3A4-substrate:	0.157

ADMET: Excretion

Clearance (CL):	7.073
Half-life (T1/2):	0.277

ADMET: Toxicity

hERG Blockers:	0.959
Human Hepatotoxicity (H-HT):	0.154
Drug-inuced Liver Injury (DILI):	0.248
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.261
Skin Sensitization:	0.974
Carcinogencity:	0.549
Eye Corrosion:	0.103
Eye Irritation:	0.359
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC99078

Natural Product ID:	NPC99078
*Common Name:**	Piperchabamide B
IUPAC Name:	(2E,10E)-11-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylundeca-2,10-dien-1-one
Synonyms:
Standard InCHIKey:	CHOLQJRIMZGPNC-QHKWOANTSA-N
Standard InCHI:	InChI=1S/C23H31NO3/c25-23(24-16-10-7-11-17-24)13-9-6-4-2-1-3-5-8-12-20-14-15-21-22(18-20)27-19-26-21/h8-9,12-15,18H,1-7,10-11,16-17,19H2/b12-8+,13-9+
SMILES:	C(CCC/C=C/C(=O)N1CCCCC1)CC/C=C/c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL255970
PubChem CID:	44453655
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO10274	Pothomorphe peltata	n.a.	n.a.	n.a.	n.a.	Dominican Republic	n.a.	PMID[11430019]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695795]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872768]
NPO3968	Dracontium loretense	Species	Araceae	Eukaryota	corms	Iquitos, Peru	2005-MAY	PMID[19341262]
NPO3968	Dracontium loretense	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19341262]
NPO10666	Verbesina virginica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19485332]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	fruits	n.a.	n.a.	PMID[20839888]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22909174]
NPO12125	Pseudomonas stutzeri	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23149469]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23434420]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[23506561]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25127165]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25988621]
NPO7158	Schefflera venulosa	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27487	Silene banksia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7158	Schefflera venulosa	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12383	Frullania brasiliensis	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12125	Pseudomonas stutzeri	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13059	Abies webbiana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12383	Frullania brasiliensis	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10666	Verbesina virginica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6428	Euphorbia wangii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27487	Silene banksia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8639	Agaricus xanthodermus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2840	Podocarpus minor	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7536	Mycoplasma mycoides	Species	Mycoplasmataceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11137	Dichotomanthes tristaniicarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO964	Homalium laurifolium	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9950	Coelogyne nitida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10459	Brickellia longifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3968	Dracontium loretense	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO230	Palisota barteri	Species	Commelinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10274	Pothomorphe peltata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO11511	Cochlearia officinalis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9166	Monascus rubropunctatus	Species	Fellodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO43	Leifsonia aquatica	Species	Microbacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO876	Didymosphaeria enalia	Species	Didymosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7158	Schefflera venulosa	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6880	Crocus corsicus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12488	Bupleurum rigidum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23642	Penicillium tardum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2393	Matsumurella chinensis	Species	Lamiaceae	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
IC50	2
Others	18

Activity Type	# Activity
Cell Line	16
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	63.0	%	PMID[448530]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	74.0	%	PMID[448530]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	78.0	%	PMID[448530]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	-14.1	%	PMID[448531]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	-2.2	%	PMID[448531]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	-3.5	%	PMID[448531]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	-30.3	%	PMID[448531]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	12.0	%	PMID[448532]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	19.0	%	PMID[448532]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	74.0	%	PMID[448532]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	94.0	%	PMID[448532]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	78.0	%	PMID[448532]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	63.0	%	PMID[448532]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	4.0	%	PMID[448532]
NPT993	Cell Line	Hepatocyte	Mus musculus	IC50	<	3000.0	nM	PMID[448532]
NPT1460	Cell Line	L929	Mus musculus	IC50	=	33000.0	nM	PMID[448532]
NPT2	Others	Unspecified		Inhibition	=	5.0	%	PMID[448532]
NPT2	Others	Unspecified		Inhibition	=	24.0	%	PMID[448532]
NPT2	Others	Unspecified		Inhibition	=	99.0	%	PMID[448532]
NPT2	Others	Unspecified		Inhibition	=	11.0	%	PMID[448532]

☑ 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 NPC99078 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	253
0.1-0.2	1477
0.2-0.3	6292
0.3-0.4	12164
0.4-0.5	5876
0.5-0.6	12622
0.6-0.7	3597
0.7-0.8	370
0.8-0.85	9
0.85-0.9	9
0.9-0.95	15
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9922	High Similarity	NPC136330
0.9922	High Similarity	NPC277042
0.9922	High Similarity	NPC73883
0.9922	High Similarity	NPC255817
0.9922	High Similarity	NPC251454
0.9922	High Similarity	NPC196609
0.9922	High Similarity	NPC230698
0.9922	High Similarity	NPC252107
0.9922	High Similarity	NPC205178
0.9922	High Similarity	NPC220923
0.9844	High Similarity	NPC167096
0.9769	High Similarity	NPC470707
0.9466	High Similarity	NPC96406
0.9394	High Similarity	NPC145446
0.9394	High Similarity	NPC137172
0.9389	High Similarity	NPC94280
0.9389	High Similarity	NPC328419
0.9389	High Similarity	NPC159150
0.9389	High Similarity	NPC103947
0.9389	High Similarity	NPC193673
0.9389	High Similarity	NPC45783
0.9323	High Similarity	NPC248505
0.9323	High Similarity	NPC225745
0.9323	High Similarity	NPC95366
0.9318	High Similarity	NPC180647
0.9237	High Similarity	NPC217574
0.9104	High Similarity	NPC469808
0.8951	High Similarity	NPC471073
0.8951	High Similarity	NPC270811
0.8947	High Similarity	NPC318862
0.8897	High Similarity	NPC28641
0.8897	High Similarity	NPC194359
0.8832	High Similarity	NPC231572
0.8652	High Similarity	NPC244338
0.8592	High Similarity	NPC469978
0.8571	High Similarity	NPC169742
0.8356	Intermediate Similarity	NPC470088
0.8301	Intermediate Similarity	NPC231198
0.8286	Intermediate Similarity	NPC416184
0.8286	Intermediate Similarity	NPC7018
0.8255	Intermediate Similarity	NPC470708
0.8227	Intermediate Similarity	NPC214036
0.8227	Intermediate Similarity	NPC113236
0.8176	Intermediate Similarity	NPC223125
0.8106	Intermediate Similarity	NPC69670
0.8067	Intermediate Similarity	NPC223124
0.8041	Intermediate Similarity	NPC475959
0.8039	Intermediate Similarity	NPC106786
0.8029	Intermediate Similarity	NPC218323
0.8015	Intermediate Similarity	NPC111225
0.8	Intermediate Similarity	NPC118419
0.8	Intermediate Similarity	NPC59567
0.8	Intermediate Similarity	NPC256167
0.7986	Intermediate Similarity	NPC470706
0.7971	Intermediate Similarity	NPC172403
0.7955	Intermediate Similarity	NPC212643
0.7955	Intermediate Similarity	NPC199209
0.7926	Intermediate Similarity	NPC114845
0.7911	Intermediate Similarity	NPC241055
0.7899	Intermediate Similarity	NPC251466
0.7899	Intermediate Similarity	NPC156944
0.7857	Intermediate Similarity	NPC160193
0.7842	Intermediate Similarity	NPC191302
0.7842	Intermediate Similarity	NPC41331
0.7842	Intermediate Similarity	NPC157740
0.7842	Intermediate Similarity	NPC64948
0.7842	Intermediate Similarity	NPC291449
0.7842	Intermediate Similarity	NPC99798
0.7836	Intermediate Similarity	NPC57501
0.7832	Intermediate Similarity	NPC11147
0.7829	Intermediate Similarity	NPC31279
0.7829	Intermediate Similarity	NPC148898
0.7826	Intermediate Similarity	NPC246133
0.7826	Intermediate Similarity	NPC71105
0.7826	Intermediate Similarity	NPC152186
0.7826	Intermediate Similarity	NPC170583
0.7826	Intermediate Similarity	NPC182147
0.7826	Intermediate Similarity	NPC207541
0.7786	Intermediate Similarity	NPC469977
0.7786	Intermediate Similarity	NPC147247
0.7786	Intermediate Similarity	NPC246974
0.7763	Intermediate Similarity	NPC119669
0.7762	Intermediate Similarity	NPC473463
0.7754	Intermediate Similarity	NPC300955
0.7752	Intermediate Similarity	NPC127326
0.7727	Intermediate Similarity	NPC93593
0.7727	Intermediate Similarity	NPC78733
0.7727	Intermediate Similarity	NPC216459
0.7727	Intermediate Similarity	NPC138487
0.7727	Intermediate Similarity	NPC41178
0.7727	Intermediate Similarity	NPC76079
0.7724	Intermediate Similarity	NPC193528
0.7722	Intermediate Similarity	NPC168409
0.7722	Intermediate Similarity	NPC306669
0.7718	Intermediate Similarity	NPC145304
0.7712	Intermediate Similarity	NPC233029
0.7712	Intermediate Similarity	NPC210148
0.7698	Intermediate Similarity	NPC85830
0.7692	Intermediate Similarity	NPC266425
0.7682	Intermediate Similarity	NPC59907
0.7682	Intermediate Similarity	NPC37144
0.7677	Intermediate Similarity	NPC31311
0.7677	Intermediate Similarity	NPC234392
0.7677	Intermediate Similarity	NPC146288
0.7664	Intermediate Similarity	NPC193484
0.7651	Intermediate Similarity	NPC116007
0.7647	Intermediate Similarity	NPC344161
0.7647	Intermediate Similarity	NPC476579
0.7639	Intermediate Similarity	NPC284855
0.7639	Intermediate Similarity	NPC282477
0.7619	Intermediate Similarity	NPC314682
0.7609	Intermediate Similarity	NPC298486
0.7603	Intermediate Similarity	NPC254610
0.7586	Intermediate Similarity	NPC475828
0.7568	Intermediate Similarity	NPC213206
0.7568	Intermediate Similarity	NPC188163
0.7568	Intermediate Similarity	NPC474915
0.7568	Intermediate Similarity	NPC328750
0.756	Intermediate Similarity	NPC477259
0.756	Intermediate Similarity	NPC169387
0.756	Intermediate Similarity	NPC471650
0.7552	Intermediate Similarity	NPC477705
0.7552	Intermediate Similarity	NPC477694
0.7546	Intermediate Similarity	NPC4669
0.7545	Intermediate Similarity	NPC83511
0.7536	Intermediate Similarity	NPC301641
0.7536	Intermediate Similarity	NPC80241
0.7532	Intermediate Similarity	NPC477559
0.7532	Intermediate Similarity	NPC85747
0.7532	Intermediate Similarity	NPC160298
0.7532	Intermediate Similarity	NPC266753
0.7532	Intermediate Similarity	NPC232924
0.7532	Intermediate Similarity	NPC215829
0.7532	Intermediate Similarity	NPC97072
0.7532	Intermediate Similarity	NPC306902
0.7532	Intermediate Similarity	NPC8337
0.7532	Intermediate Similarity	NPC474852
0.7516	Intermediate Similarity	NPC211296
0.75	Intermediate Similarity	NPC477706
0.75	Intermediate Similarity	NPC95075
0.75	Intermediate Similarity	NPC253883
0.75	Intermediate Similarity	NPC90844
0.75	Intermediate Similarity	NPC277460
0.7485	Intermediate Similarity	NPC102760
0.7485	Intermediate Similarity	NPC303581
0.7485	Intermediate Similarity	NPC67978
0.7484	Intermediate Similarity	NPC476580
0.7483	Intermediate Similarity	NPC130926
0.7481	Intermediate Similarity	NPC268317
0.7469	Intermediate Similarity	NPC86469
0.7468	Intermediate Similarity	NPC118804
0.7468	Intermediate Similarity	NPC329640
0.7468	Intermediate Similarity	NPC477080
0.7468	Intermediate Similarity	NPC111485
0.7465	Intermediate Similarity	NPC286683
0.7448	Intermediate Similarity	NPC160692
0.7429	Intermediate Similarity	NPC249788
0.7426	Intermediate Similarity	NPC185738
0.7426	Intermediate Similarity	NPC120075
0.7426	Intermediate Similarity	NPC280001
0.7424	Intermediate Similarity	NPC179309
0.7421	Intermediate Similarity	NPC135006
0.7415	Intermediate Similarity	NPC167944
0.7415	Intermediate Similarity	NPC131204
0.7415	Intermediate Similarity	NPC231884
0.7415	Intermediate Similarity	NPC301050
0.7415	Intermediate Similarity	NPC42793
0.7415	Intermediate Similarity	NPC307682
0.7407	Intermediate Similarity	NPC474324
0.7407	Intermediate Similarity	NPC57812
0.7403	Intermediate Similarity	NPC469539
0.7403	Intermediate Similarity	NPC469540
0.7403	Intermediate Similarity	NPC219162
0.74	Intermediate Similarity	NPC908
0.74	Intermediate Similarity	NPC138438
0.7394	Intermediate Similarity	NPC181905
0.7394	Intermediate Similarity	NPC301713
0.7394	Intermediate Similarity	NPC308267
0.7391	Intermediate Similarity	NPC238530
0.7391	Intermediate Similarity	NPC232514
0.7391	Intermediate Similarity	NPC276944
0.7391	Intermediate Similarity	NPC225774
0.7368	Intermediate Similarity	NPC185838
0.7365	Intermediate Similarity	NPC102260
0.7365	Intermediate Similarity	NPC27887
0.7365	Intermediate Similarity	NPC253429
0.7365	Intermediate Similarity	NPC230968
0.7362	Intermediate Similarity	NPC475845
0.7361	Intermediate Similarity	NPC476748
0.7351	Intermediate Similarity	NPC128019
0.7351	Intermediate Similarity	NPC136860
0.7351	Intermediate Similarity	NPC476567
0.7346	Intermediate Similarity	NPC24264
0.7346	Intermediate Similarity	NPC476432
0.7346	Intermediate Similarity	NPC219341
0.7346	Intermediate Similarity	NPC474858
0.7342	Intermediate Similarity	NPC57512
0.7338	Intermediate Similarity	NPC471877
0.7333	Intermediate Similarity	NPC275150
0.7333	Intermediate Similarity	NPC294941

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 NPC99078 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	722
0.2-0.3	1010
0.3-0.4	2286
0.4-0.5	2710
0.5-0.6	1603
0.6-0.7	562
0.7-0.8	80
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9922	High Similarity	NPD2492	Phase 1
0.8403	Intermediate Similarity	NPD5297	Approved
0.8082	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD5718	Phase 2
0.7891	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD3885	Approved
0.7606	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7110	Phase 1
0.7532	Intermediate Similarity	NPD824	Approved
0.7516	Intermediate Similarity	NPD5977	Approved
0.7516	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5978	Approved
0.7468	Intermediate Similarity	NPD4210	Discontinued
0.7426	Intermediate Similarity	NPD5536	Phase 2
0.7421	Intermediate Similarity	NPD5604	Discontinued
0.7415	Intermediate Similarity	NPD6895	Approved
0.7415	Intermediate Similarity	NPD6896	Approved
0.74	Intermediate Similarity	NPD4237	Approved
0.74	Intermediate Similarity	NPD4236	Phase 3
0.7391	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2653	Approved
0.7346	Intermediate Similarity	NPD4166	Phase 2
0.7329	Intermediate Similarity	NPD3140	Approved
0.7329	Intermediate Similarity	NPD3142	Approved
0.7325	Intermediate Similarity	NPD6386	Approved
0.7325	Intermediate Similarity	NPD6873	Phase 2
0.7325	Intermediate Similarity	NPD6385	Approved
0.7321	Intermediate Similarity	NPD7281	Phase 3
0.7321	Intermediate Similarity	NPD7280	Phase 3
0.7319	Intermediate Similarity	NPD1357	Approved
0.7305	Intermediate Similarity	NPD1421	Approved
0.7305	Intermediate Similarity	NPD1420	Approved
0.7297	Intermediate Similarity	NPD743	Approved
0.729	Intermediate Similarity	NPD3639	Approved
0.729	Intermediate Similarity	NPD3640	Phase 3
0.729	Intermediate Similarity	NPD3641	Approved
0.7286	Intermediate Similarity	NPD3705	Approved
0.7273	Intermediate Similarity	NPD3146	Approved
0.7273	Intermediate Similarity	NPD4584	Approved
0.7273	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6876	Approved
0.7261	Intermediate Similarity	NPD6875	Approved
0.7233	Intermediate Similarity	NPD2977	Approved
0.7233	Intermediate Similarity	NPD2978	Approved
0.7232	Intermediate Similarity	NPD5457	Discontinued
0.7181	Intermediate Similarity	NPD6111	Discontinued
0.7171	Intermediate Similarity	NPD5177	Phase 3
0.7152	Intermediate Similarity	NPD2898	Approved
0.7152	Intermediate Similarity	NPD3656	Approved
0.7143	Intermediate Similarity	NPD2668	Approved
0.7143	Intermediate Similarity	NPD3531	Approved
0.7143	Intermediate Similarity	NPD2667	Approved
0.7143	Intermediate Similarity	NPD3530	Approved
0.7143	Intermediate Similarity	NPD2674	Phase 3
0.7143	Intermediate Similarity	NPD2245	Discovery
0.7143	Intermediate Similarity	NPD3532	Approved
0.7133	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5283	Phase 1
0.7114	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4357	Discontinued
0.7089	Intermediate Similarity	NPD4017	Approved
0.7086	Intermediate Similarity	NPD1725	Approved
0.7078	Intermediate Similarity	NPD5241	Discontinued
0.7078	Intermediate Similarity	NPD2219	Phase 1
0.7076	Intermediate Similarity	NPD6618	Phase 2
0.7075	Intermediate Similarity	NPD3144	Approved
0.7075	Intermediate Similarity	NPD3145	Approved
0.7071	Intermediate Similarity	NPD6382	Discontinued
0.707	Intermediate Similarity	NPD6031	Approved
0.707	Intermediate Similarity	NPD6030	Approved
0.7063	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3060	Approved
0.7059	Intermediate Similarity	NPD4162	Approved
0.7052	Intermediate Similarity	NPD3349	Phase 2
0.7051	Intermediate Similarity	NPD1424	Approved
0.7041	Intermediate Similarity	NPD6297	Approved
0.7039	Intermediate Similarity	NPD1375	Discontinued
0.7033	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7124	Phase 2
0.7024	Intermediate Similarity	NPD5313	Approved
0.7024	Intermediate Similarity	NPD5312	Approved
0.7013	Intermediate Similarity	NPD5481	Discontinued
0.6993	Remote Similarity	NPD2232	Approved
0.6993	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2230	Approved
0.6993	Remote Similarity	NPD2233	Approved
0.698	Remote Similarity	NPD3110	Approved
0.698	Remote Similarity	NPD3109	Approved
0.6975	Remote Similarity	NPD5353	Approved
0.6972	Remote Similarity	NPD3447	Discontinued
0.6968	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2122	Discontinued
0.6962	Remote Similarity	NPD1670	Discontinued
0.6962	Remote Similarity	NPD4727	Phase 1
0.6959	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3383	Approved
0.6957	Remote Similarity	NPD3384	Approved
0.6957	Remote Similarity	NPD3382	Approved
0.6954	Remote Similarity	NPD7119	Phase 2
0.6954	Remote Similarity	NPD7291	Discontinued
0.6949	Remote Similarity	NPD6493	Phase 3
0.6946	Remote Similarity	NPD4481	Phase 3
0.6943	Remote Similarity	NPD4739	Approved
0.694	Remote Similarity	NPD1358	Approved
0.6923	Remote Similarity	NPD5295	Discontinued
0.6923	Remote Similarity	NPD2120	Phase 2
0.6918	Remote Similarity	NPD7905	Discontinued
0.6918	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5773	Approved
0.6914	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5772	Approved
0.6914	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5582	Discontinued
0.6909	Remote Similarity	NPD5677	Discontinued
0.6899	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2922	Phase 1
0.6894	Remote Similarity	NPD4773	Phase 2
0.6894	Remote Similarity	NPD4772	Phase 2
0.6892	Remote Similarity	NPD5746	Approved
0.6879	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6853	Approved
0.6879	Remote Similarity	NPD6851	Approved
0.6875	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2560	Approved
0.6871	Remote Similarity	NPD2563	Approved
0.6867	Remote Similarity	NPD6107	Approved
0.6866	Remote Similarity	NPD3134	Approved
0.6863	Remote Similarity	NPD2161	Phase 2
0.6861	Remote Similarity	NPD228	Approved
0.686	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3596	Phase 2
0.6855	Remote Similarity	NPD5976	Discontinued
0.6855	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7298	Approved
0.6849	Remote Similarity	NPD4098	Discontinued
0.6846	Remote Similarity	NPD1336	Approved
0.6835	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD4420	Approved
0.6831	Remote Similarity	NPD2594	Approved
0.6831	Remote Similarity	NPD2595	Approved
0.6829	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6788	Approved
0.6826	Remote Similarity	NPD6071	Discontinued
0.6815	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3687	Approved
0.6813	Remote Similarity	NPD3686	Approved
0.681	Remote Similarity	NPD4585	Approved
0.6807	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7018	Phase 2
0.68	Remote Similarity	NPD5745	Approved
0.6797	Remote Similarity	NPD4108	Discontinued
0.6795	Remote Similarity	NPD5754	Discontinued
0.6795	Remote Similarity	NPD6331	Phase 2
0.6792	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1307	Phase 2
0.6788	Remote Similarity	NPD1309	Phase 2
0.6786	Remote Similarity	NPD5242	Approved
0.6786	Remote Similarity	NPD2388	Discontinued
0.6779	Remote Similarity	NPD5163	Phase 2
0.6774	Remote Similarity	NPD7153	Discontinued
0.677	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5967	Approved
0.6763	Remote Similarity	NPD7549	Discontinued
0.6761	Remote Similarity	NPD2486	Discontinued
0.6736	Remote Similarity	NPD3294	Phase 2
0.6733	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD1039	Discontinued
0.673	Remote Similarity	NPD2335	Discontinued
0.673	Remote Similarity	NPD4123	Phase 3
0.6728	Remote Similarity	NPD2592	Discontinued
0.6726	Remote Similarity	NPD3051	Approved
0.6723	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD1669	Approved
0.671	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2904	Discontinued
0.6705	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6584	Phase 3
0.6688	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7833	Phase 2
0.6687	Remote Similarity	NPD8031	Discontinued
0.6687	Remote Similarity	NPD5090	Approved
0.6687	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5089	Approved
0.6687	Remote Similarity	NPD7831	Phase 2
0.6687	Remote Similarity	NPD7832	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