NPASS Compound

Structure

NPC279291 OpenBabel07101719522D 34 37 0 0 1 0 0 0 0 0999 V2000 0.8435 1.5128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0449 2.9997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6195 2.4242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6195 2.4242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 0.9999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6195 -2.3645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3600 -1.5775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2430 -0.0896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3930 -0.9195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0204 -1.0646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8884 1.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5604 -2.5386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3371 0.4352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0299 1.9998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5753 -1.5387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4637 -0.0518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6195 0.6922 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2185 -1.0646 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8734 0.4870 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7319 -0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6195 0.6922 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9960 -0.0896 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4488 -1.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7169 -1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6053 0.4611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1195 1.5582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1195 -1.4985 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4188 -3.0515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1956 -0.0777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3072 -1.5646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8435 -1.5128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6202 1.4610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6195 -2.3645 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 9 1 0 0 0 0 7 18 1 0 0 0 0 8 10 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 12 29 2 0 0 0 0 13 16 1 0 0 0 0 13 30 2 0 0 0 0 15 23 2 0 0 0 0 15 24 1 0 0 0 0 16 23 1 0 0 0 0 16 25 2 0 0 0 0 17 8 1 6 0 0 0 17 21 1 0 0 0 0 17 26 1 0 0 0 0 18 22 1 0 0 0 0 18 28 1 6 0 0 0 19 11 1 1 0 0 0 19 20 1 0 0 0 0 19 27 1 0 0 0 0 20 24 2 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 21 26 1 6 0 0 0 22 27 1 1 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 27 5 1 1 0 0 0 28 6 1 6 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.28
Volume:	498.177
LogP:	7.385
LogD:	4.804
LogS:	-3.58
# Rotatable Bonds:	6
TPSA:	115.06
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.412
Synthetic Accessibility Score:	5.006
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.816
MDCK Permeability:	9.546529327053577e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.133
Plasma Protein Binding (PPB):	100.19994354248047%
Volume Distribution (VD):	1.838
Pgp-substrate:	2.897361993789673%

ADMET: Metabolism

CYP1A2-inhibitor:	0.142
CYP1A2-substrate:	0.225
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.444
CYP2C9-inhibitor:	0.67
CYP2C9-substrate:	0.936
CYP2D6-inhibitor:	0.093
CYP2D6-substrate:	0.152
CYP3A4-inhibitor:	0.172
CYP3A4-substrate:	0.19

ADMET: Excretion

Clearance (CL):	1.843
Half-life (T1/2):	0.208

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.061
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.216
Maximum Recommended Daily Dose:	0.902
Skin Sensitization:	0.781
Carcinogencity:	0.076
Eye Corrosion:	0.104
Eye Irritation:	0.837
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC279291

Natural Product ID:	NPC279291
*Common Name:**	Macrocarpal B
IUPAC Name:	5-[(1S)-1-[(1aR,4R,4aR,7S,7aS,7bR)-4-hydroxy-1,1,4,7-tetramethyl-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde
Synonyms:
Standard InCHIKey:	IBLPTYJTKWQCDX-NGLILROZSA-N
Standard InCHI:	InChI=1S/C28H40O6/c1-14(2)11-19(20-24(32)15(12-29)23(31)16(13-30)25(20)33)27(5)9-7-18-22(27)21-17(26(21,3)4)8-10-28(18,6)34/h12-14,17-19,21-22,31-34H,7-11H2,1-6H3/t17-,18-,19-,21-,22-,27-,28-/m1/s1
SMILES:	O=Cc1c(O)c(c(c(c1O)C=O)O)[C@H]([C@@]1(C)CC[C@@H]2[C@@H]1[C@H]1[C@H](C1(C)C)CC[C@@]2(C)O)CC(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL396848
PubChem CID:	454458
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001781] Aromadendrane sesquiterpenoids [CHEMONTID:0003562] 5,10-cycloaromadendrane sesquiterpenoids

*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
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	fruit	n.a.	PMID[18020353]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22934600]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[23678820]
NPO7175	Eucalyptus robusta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27142786]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[30543429]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[30848923]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[8864235]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7175	Eucalyptus robusta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7175	Eucalyptus robusta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7175	Eucalyptus robusta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7175	Eucalyptus robusta	Species	Myrtaceae	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	3
MIC	10
Others	26

Activity Type	# Activity
Cell Line	21
NON-MOLECULAR	2
Organism	10
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT492	Cell Line	Caco-2	Homo sapiens	Papp	=	2.29	10^-6 cm/s	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Papp	=	1.71	10^-6 cm/s	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Papp	=	1.64	10^-6 cm/s	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Papp	=	1.84	10^-6 cm/s	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Papp	=	2.0	10^-6 cm/s	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Papp	=	2.14	10^-6 cm/s	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Ratio	=	1.25	n.a.	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Ratio	=	0.85	n.a.	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Ratio	=	0.77	n.a.	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Drug uptake	=	41.19	%	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Drug uptake	=	50.56	%	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Drug uptake	=	46.98	%	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Drug uptake	=	63.25	%	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Drug uptake	=	53.21	%	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Drug uptake	=	49.26	%	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Drug uptake	=	49.99	%	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Drug uptake	=	56.63	%	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Drug uptake	=	64.67	%	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Drug uptake	=	68.72	%	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Drug uptake	=	59.47	%	PMID[490619]
NPT492	Cell Line	Caco-2	Homo sapiens	Drug uptake	=	55.54	%	PMID[490619]
NPT1128	Organism	Prevotella intermedia	Prevotella intermedia	MIC	=	1.56	ug.mL-1	PMID[490620]
NPT5408	Organism	Capnocytophaga ochracea	Capnocytophaga ochracea	MIC	=	1.56	ug.mL-1	PMID[490620]
NPT1484	Organism	Fusobacterium nucleatum	Fusobacterium nucleatum	MIC	=	3.13	ug.mL-1	PMID[490620]
NPT2	Others	Unspecified		Inhibition	=	97.1	%	PMID[490620]
NPT2	Others	Unspecified		Inhibition	=	67.6	%	PMID[490620]
NPT2	Others	Unspecified		Inhibition	=	10.1	%	PMID[490620]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	3.13	ug.mL-1	PMID[490620]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	1.56	ug.mL-1	PMID[490620]
NPT1483	Organism	Streptococcus sobrinus	Streptococcus sobrinus	MIC	=	3.13	ug.mL-1	PMID[490620]
NPT1129	Organism	Actinomyces viscosus	Actinomyces viscosus	MIC	=	0.39	ug.mL-1	PMID[490620]
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MIC	=	0.78	ug.mL-1	PMID[490620]
NPT4829	Organism	Prevotella melaninogenica	Prevotella melaninogenica	MIC	=	3.13	ug.mL-1	PMID[490620]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	<	10000.0	nM	PMID[490622]
NPT2	Others	Unspecified		CC50	=	570200.0	nM	PMID[490623]
NPT2	Others	Unspecified		IC50	=	31200.0	nM	PMID[490623]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	18.4	n.a.	PMID[490623]

☑ 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 NPC279291 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	354
0.1-0.2	1615
0.2-0.3	3597
0.3-0.4	10670
0.4-0.5	11479
0.5-0.6	8871
0.6-0.7	5627
0.7-0.8	441
0.8-0.85	18
0.85-0.9	5
0.9-0.95	9
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC244640
0.9846	High Similarity	NPC147691
0.9769	High Similarity	NPC299734
0.9612	High Similarity	NPC474109
0.9394	High Similarity	NPC474076
0.8889	High Similarity	NPC474224
0.8889	High Similarity	NPC474117
0.8824	High Similarity	NPC475917
0.8769	High Similarity	NPC306288
0.8692	High Similarity	NPC218333
0.8382	Intermediate Similarity	NPC73203
0.8271	Intermediate Similarity	NPC66252
0.8222	Intermediate Similarity	NPC475733
0.8175	Intermediate Similarity	NPC475553
0.8175	Intermediate Similarity	NPC164894
0.8162	Intermediate Similarity	NPC328983
0.8134	Intermediate Similarity	NPC232708
0.8129	Intermediate Similarity	NPC275504
0.812	Intermediate Similarity	NPC229649
0.8102	Intermediate Similarity	NPC316625
0.8102	Intermediate Similarity	NPC329205
0.8088	Intermediate Similarity	NPC290466
0.8085	Intermediate Similarity	NPC475088
0.8074	Intermediate Similarity	NPC472029
0.8074	Intermediate Similarity	NPC65761
0.8056	Intermediate Similarity	NPC162939
0.8	Intermediate Similarity	NPC91105
0.7987	Intermediate Similarity	NPC245757
0.7987	Intermediate Similarity	NPC304351
0.7986	Intermediate Similarity	NPC476119
0.7971	Intermediate Similarity	NPC19432
0.7958	Intermediate Similarity	NPC474519
0.7958	Intermediate Similarity	NPC218854
0.7958	Intermediate Similarity	NPC52368
0.7929	Intermediate Similarity	NPC62219
0.7926	Intermediate Similarity	NPC226275
0.7926	Intermediate Similarity	NPC215392
0.7905	Intermediate Similarity	NPC5990
0.7902	Intermediate Similarity	NPC278375
0.7891	Intermediate Similarity	NPC81337
0.7891	Intermediate Similarity	NPC157497
0.7891	Intermediate Similarity	NPC285659
0.7887	Intermediate Similarity	NPC103105
0.7887	Intermediate Similarity	NPC285054
0.7883	Intermediate Similarity	NPC12818
0.7862	Intermediate Similarity	NPC477593
0.7862	Intermediate Similarity	NPC473622
0.7857	Intermediate Similarity	NPC474998
0.7852	Intermediate Similarity	NPC146642
0.7852	Intermediate Similarity	NPC149246
0.7842	Intermediate Similarity	NPC116513
0.7832	Intermediate Similarity	NPC470984
0.78	Intermediate Similarity	NPC82534
0.7794	Intermediate Similarity	NPC303737
0.7792	Intermediate Similarity	NPC470102
0.7786	Intermediate Similarity	NPC470981
0.7786	Intermediate Similarity	NPC21305
0.7786	Intermediate Similarity	NPC473017
0.7778	Intermediate Similarity	NPC294037
0.777	Intermediate Similarity	NPC473691
0.777	Intermediate Similarity	NPC267846
0.7762	Intermediate Similarity	NPC139074
0.7762	Intermediate Similarity	NPC37299
0.7762	Intermediate Similarity	NPC180261
0.7762	Intermediate Similarity	NPC470988
0.7762	Intermediate Similarity	NPC213485
0.7762	Intermediate Similarity	NPC40524
0.7746	Intermediate Similarity	NPC475042
0.7746	Intermediate Similarity	NPC279566
0.774	Intermediate Similarity	NPC322301
0.774	Intermediate Similarity	NPC255801
0.7737	Intermediate Similarity	NPC309765
0.7724	Intermediate Similarity	NPC471690
0.7714	Intermediate Similarity	NPC72158
0.7714	Intermediate Similarity	NPC266689
0.7714	Intermediate Similarity	NPC190043
0.7714	Intermediate Similarity	NPC169250
0.7714	Intermediate Similarity	NPC100067
0.7714	Intermediate Similarity	NPC162612
0.7714	Intermediate Similarity	NPC23126
0.7714	Intermediate Similarity	NPC30501
0.7714	Intermediate Similarity	NPC103356
0.7714	Intermediate Similarity	NPC105157
0.7714	Intermediate Similarity	NPC98254
0.7698	Intermediate Similarity	NPC477454
0.7692	Intermediate Similarity	NPC175738
0.7692	Intermediate Similarity	NPC27490
0.7692	Intermediate Similarity	NPC185624
0.7687	Intermediate Similarity	NPC230349
0.7687	Intermediate Similarity	NPC174087
0.7676	Intermediate Similarity	NPC186628
0.7676	Intermediate Similarity	NPC17840
0.7676	Intermediate Similarity	NPC247477
0.7676	Intermediate Similarity	NPC296158
0.7671	Intermediate Similarity	NPC470985
0.7671	Intermediate Similarity	NPC194579
0.7671	Intermediate Similarity	NPC470989
0.7671	Intermediate Similarity	NPC477592
0.7671	Intermediate Similarity	NPC245058
0.766	Intermediate Similarity	NPC221777
0.7655	Intermediate Similarity	NPC290803
0.7655	Intermediate Similarity	NPC130899
0.7655	Intermediate Similarity	NPC61153
0.7655	Intermediate Similarity	NPC283590
0.7655	Intermediate Similarity	NPC70859
0.7651	Intermediate Similarity	NPC476508
0.7651	Intermediate Similarity	NPC111201
0.7643	Intermediate Similarity	NPC62952
0.7635	Intermediate Similarity	NPC99441
0.7635	Intermediate Similarity	NPC270913
0.763	Intermediate Similarity	NPC209486
0.763	Intermediate Similarity	NPC40649
0.7628	Intermediate Similarity	NPC470344
0.7622	Intermediate Similarity	NPC324482
0.7603	Intermediate Similarity	NPC475955
0.7603	Intermediate Similarity	NPC191976
0.7603	Intermediate Similarity	NPC472599
0.7603	Intermediate Similarity	NPC474726
0.7603	Intermediate Similarity	NPC156967
0.7589	Intermediate Similarity	NPC83572
0.7586	Intermediate Similarity	NPC166480
0.7586	Intermediate Similarity	NPC474394
0.7586	Intermediate Similarity	NPC282780
0.7586	Intermediate Similarity	NPC16197
0.7586	Intermediate Similarity	NPC477594
0.7584	Intermediate Similarity	NPC477272
0.7584	Intermediate Similarity	NPC289660
0.7584	Intermediate Similarity	NPC82920
0.7584	Intermediate Similarity	NPC164697
0.7584	Intermediate Similarity	NPC37530
0.7584	Intermediate Similarity	NPC11056
0.7584	Intermediate Similarity	NPC92079
0.7568	Intermediate Similarity	NPC477056
0.7568	Intermediate Similarity	NPC471620
0.7568	Intermediate Similarity	NPC477055
0.7566	Intermediate Similarity	NPC476535
0.7552	Intermediate Similarity	NPC21378
0.7552	Intermediate Similarity	NPC259942
0.7552	Intermediate Similarity	NPC470987
0.7552	Intermediate Similarity	NPC84772
0.7551	Intermediate Similarity	NPC156910
0.7551	Intermediate Similarity	NPC53001
0.7551	Intermediate Similarity	NPC65837
0.7551	Intermediate Similarity	NPC222633
0.7551	Intermediate Similarity	NPC474771
0.7551	Intermediate Similarity	NPC71256
0.7551	Intermediate Similarity	NPC149372
0.7551	Intermediate Similarity	NPC474849
0.7551	Intermediate Similarity	NPC178467
0.7534	Intermediate Similarity	NPC470210
0.7534	Intermediate Similarity	NPC477596
0.7533	Intermediate Similarity	NPC74397
0.7533	Intermediate Similarity	NPC474961
0.7518	Intermediate Similarity	NPC473751
0.7517	Intermediate Similarity	NPC472601
0.7517	Intermediate Similarity	NPC215875
0.7517	Intermediate Similarity	NPC15834
0.7517	Intermediate Similarity	NPC470986
0.7517	Intermediate Similarity	NPC48036
0.7517	Intermediate Similarity	NPC472600
0.75	Intermediate Similarity	NPC476055
0.75	Intermediate Similarity	NPC87723
0.75	Intermediate Similarity	NPC283844
0.75	Intermediate Similarity	NPC41847
0.75	Intermediate Similarity	NPC470673
0.75	Intermediate Similarity	NPC250057
0.75	Intermediate Similarity	NPC117716
0.75	Intermediate Similarity	NPC475974
0.75	Intermediate Similarity	NPC472403
0.75	Intermediate Similarity	NPC470674
0.7484	Intermediate Similarity	NPC476509
0.7483	Intermediate Similarity	NPC230818
0.7483	Intermediate Similarity	NPC118919
0.7483	Intermediate Similarity	NPC84699
0.7483	Intermediate Similarity	NPC297600
0.7483	Intermediate Similarity	NPC474546
0.7483	Intermediate Similarity	NPC92624
0.7483	Intermediate Similarity	NPC325346
0.7483	Intermediate Similarity	NPC101752
0.7483	Intermediate Similarity	NPC276565
0.7483	Intermediate Similarity	NPC472344
0.7469	Intermediate Similarity	NPC211592
0.7468	Intermediate Similarity	NPC25850
0.7468	Intermediate Similarity	NPC276815
0.7467	Intermediate Similarity	NPC469818
0.7467	Intermediate Similarity	NPC472605
0.7467	Intermediate Similarity	NPC472604
0.7467	Intermediate Similarity	NPC187843
0.7467	Intermediate Similarity	NPC477595
0.7467	Intermediate Similarity	NPC471587
0.7467	Intermediate Similarity	NPC472603
0.7466	Intermediate Similarity	NPC270899
0.7451	Intermediate Similarity	NPC473023
0.745	Intermediate Similarity	NPC275356
0.745	Intermediate Similarity	NPC21350
0.745	Intermediate Similarity	NPC474504
0.745	Intermediate Similarity	NPC474487
0.745	Intermediate Similarity	NPC470672
0.745	Intermediate Similarity	NPC88269
0.745	Intermediate Similarity	NPC131130

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 NPC279291 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	1112
0.2-0.3	2267
0.3-0.4	3110
0.4-0.5	1753
0.5-0.6	505
0.6-0.7	95
0.7-0.8	4
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
0.7958	Intermediate Similarity	NPD6651	Approved
0.7517	Intermediate Similarity	NPD2800	Approved
0.7386	Intermediate Similarity	NPD2534	Approved
0.7386	Intermediate Similarity	NPD2533	Approved
0.7386	Intermediate Similarity	NPD2532	Approved
0.7248	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7390	Discontinued
0.7051	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1510	Phase 2
0.6993	Remote Similarity	NPD970	Clinical (unspecified phase)
0.698	Remote Similarity	NPD943	Approved
0.698	Remote Similarity	NPD1240	Approved
0.6943	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1607	Approved
0.6835	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4380	Phase 2
0.6818	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7819	Suspended
0.681	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7411	Suspended
0.6788	Remote Similarity	NPD7075	Discontinued
0.6774	Remote Similarity	NPD1549	Phase 2
0.6753	Remote Similarity	NPD5408	Approved
0.6753	Remote Similarity	NPD5406	Approved
0.6753	Remote Similarity	NPD5404	Approved
0.6753	Remote Similarity	NPD5405	Approved
0.6735	Remote Similarity	NPD1164	Approved
0.6727	Remote Similarity	NPD7768	Phase 2
0.6726	Remote Similarity	NPD5711	Approved
0.6726	Remote Similarity	NPD5710	Approved
0.6707	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6959	Discontinued
0.6647	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD920	Approved
0.6645	Remote Similarity	NPD2796	Approved
0.6645	Remote Similarity	NPD2935	Discontinued
0.6626	Remote Similarity	NPD6599	Discontinued
0.6608	Remote Similarity	NPD7473	Discontinued
0.6582	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD1201	Approved
0.6552	Remote Similarity	NPD3019	Approved
0.6552	Remote Similarity	NPD2932	Approved
0.6545	Remote Similarity	NPD6801	Discontinued
0.6545	Remote Similarity	NPD1934	Approved
0.6538	Remote Similarity	NPD6099	Approved
0.6538	Remote Similarity	NPD6100	Approved
0.6538	Remote Similarity	NPD1551	Phase 2
0.6529	Remote Similarity	NPD6232	Discontinued
0.6527	Remote Similarity	NPD3882	Suspended
0.651	Remote Similarity	NPD1470	Approved
0.6506	Remote Similarity	NPD5761	Phase 2
0.6506	Remote Similarity	NPD5760	Phase 2
0.6503	Remote Similarity	NPD9493	Approved
0.65	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD230	Phase 1
0.6477	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD2799	Discontinued
0.646	Remote Similarity	NPD6799	Approved
0.6444	Remote Similarity	NPD940	Approved
0.6444	Remote Similarity	NPD846	Approved
0.6437	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.642	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD9269	Phase 2
0.6415	Remote Similarity	NPD2654	Approved
0.6415	Remote Similarity	NPD1243	Approved
0.6415	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD9545	Approved
0.6412	Remote Similarity	NPD5494	Approved
0.6407	Remote Similarity	NPD2801	Approved
0.6405	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD74	Approved
0.6403	Remote Similarity	NPD9266	Approved
0.6391	Remote Similarity	NPD3749	Approved
0.6391	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.637	Remote Similarity	NPD9268	Approved
0.6364	Remote Similarity	NPD6663	Approved
0.6364	Remote Similarity	NPD7458	Discontinued
0.6358	Remote Similarity	NPD1511	Approved
0.6357	Remote Similarity	NPD4750	Phase 3
0.6343	Remote Similarity	NPD6020	Phase 2
0.6343	Remote Similarity	NPD7286	Phase 2
0.6331	Remote Similarity	NPD9263	Approved
0.6331	Remote Similarity	NPD9267	Approved
0.6331	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD9264	Approved
0.6328	Remote Similarity	NPD6559	Discontinued
0.6316	Remote Similarity	NPD5736	Approved
0.6316	Remote Similarity	NPD1809	Phase 2
0.6294	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD2344	Approved
0.6282	Remote Similarity	NPD5124	Phase 1
0.6282	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.628	Remote Similarity	NPD1512	Approved
0.6279	Remote Similarity	NPD1247	Approved
0.6276	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD4628	Phase 3
0.6273	Remote Similarity	NPD3750	Approved
0.6271	Remote Similarity	NPD5953	Discontinued
0.6264	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6166	Phase 2
0.6257	Remote Similarity	NPD919	Approved
0.6257	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD7074	Phase 3
0.6196	Remote Similarity	NPD7236	Approved
0.6196	Remote Similarity	NPD3300	Phase 2
0.6194	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD3764	Approved
0.6194	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD3818	Discontinued
0.6188	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD6002	Phase 3
0.6188	Remote Similarity	NPD6004	Phase 3
0.6188	Remote Similarity	NPD6005	Phase 3
0.6176	Remote Similarity	NPD3817	Phase 2
0.6174	Remote Similarity	NPD3026	Approved
0.6174	Remote Similarity	NPD3023	Approved
0.6173	Remote Similarity	NPD7003	Approved
0.6171	Remote Similarity	NPD2403	Approved
0.617	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD7054	Approved
0.6154	Remote Similarity	NPD8434	Phase 2
0.6149	Remote Similarity	NPD3025	Approved
0.6149	Remote Similarity	NPD3024	Approved
0.6144	Remote Similarity	NPD2798	Approved
0.6144	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.614	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD9281	Approved
0.6135	Remote Similarity	NPD2309	Approved
0.6124	Remote Similarity	NPD7472	Approved
0.6124	Remote Similarity	NPD1729	Discontinued
0.6121	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD1876	Approved
0.6104	Remote Similarity	NPD4208	Discontinued
0.6096	Remote Similarity	NPD4361	Phase 2
0.6096	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD9717	Approved
0.6093	Remote Similarity	NPD3972	Approved
0.6087	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD3091	Approved
0.6081	Remote Similarity	NPD7741	Discontinued
0.6078	Remote Similarity	NPD3094	Phase 2
0.6074	Remote Similarity	NPD3400	Discontinued
0.6067	Remote Similarity	NPD5844	Phase 1
0.6065	Remote Similarity	NPD6832	Phase 2
0.6065	Remote Similarity	NPD4908	Phase 1
0.6065	Remote Similarity	NPD4207	Discontinued
0.6062	Remote Similarity	NPD7033	Discontinued
0.6062	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD7251	Discontinued
0.6056	Remote Similarity	NPD6104	Discontinued
0.6045	Remote Similarity	NPD845	Approved
0.6043	Remote Similarity	NPD4363	Phase 3
0.6043	Remote Similarity	NPD4360	Phase 2
0.6043	Remote Similarity	NPD9261	Approved
0.6026	Remote Similarity	NPD3092	Approved
0.6022	Remote Similarity	NPD7808	Phase 3
0.6012	Remote Similarity	NPD7239	Suspended
0.6	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4059	Approved
0.6	Remote Similarity	NPD9494	Approved
0.6	Remote Similarity	NPD6797	Phase 2
0.6	Remote Similarity	NPD7199	Phase 2
0.6	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD6273	Approved
0.5987	Remote Similarity	NPD3268	Approved
0.5987	Remote Similarity	NPD2313	Discontinued
0.5978	Remote Similarity	NPD8150	Discontinued
0.5976	Remote Similarity	NPD8166	Discontinued
0.5976	Remote Similarity	NPD3226	Approved
0.5975	Remote Similarity	NPD6355	Discontinued
0.5974	Remote Similarity	NPD1203	Approved
0.5969	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD7229	Phase 3
0.5963	Remote Similarity	NPD3748	Approved
0.5952	Remote Similarity	NPD5403	Approved
0.5949	Remote Similarity	NPD520	Approved
0.5942	Remote Similarity	NPD3020	Approved
0.5939	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD3926	Phase 2
0.5921	Remote Similarity	NPD1610	Phase 2
0.5918	Remote Similarity	NPD5951	Approved
0.5906	Remote Similarity	NPD7610	Discontinued
0.5894	Remote Similarity	NPD3095	Discontinued
0.589	Remote Similarity	NPD2346	Discontinued
0.5879	Remote Similarity	NPD7685	Pre-registration
0.5879	Remote Similarity	NPD3658	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