NPASS Compound

Structure

CID162484 OpenBabel06191715532D 22 25 0 0 0 0 0 0 0 0999 V2000 -0.0314 1.9514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0140 -0.9660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5073 -1.8440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8972 2.8767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8590 0.4819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0221 -0.0011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6733 -0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8364 -1.4496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6740 1.9327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0225 1.9321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8371 1.4497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8592 1.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6736 -0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1851 1.4491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5111 1.4494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1849 0.4822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5109 0.4826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8369 0.4829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 -0.9662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3481 -0.0008 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.6961 1.9317 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 11 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 4 21 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 16 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 11 18 2 0 0 0 0 12 21 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 14 16 2 0 0 0 0 15 17 1 0 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 18 22 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	293.14
Volume:	313.076
LogP:	5.573
LogD:	4.678
LogS:	-5.653
# Rotatable Bonds:	1
TPSA:	34.25
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.698
Synthetic Accessibility Score:	2.71
Fsp3:	0.263
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:	-4.997
MDCK Permeability:	1.4500394172500819e-05
Pgp-inhibitor:	0.948
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.206

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.408
Plasma Protein Binding (PPB):	98.36835479736328%
Volume Distribution (VD):	0.807
Pgp-substrate:	1.4407786130905151%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.925
CYP2C19-substrate:	0.552
CYP2C9-inhibitor:	0.807
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.946
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.775
CYP3A4-substrate:	0.396

ADMET: Excretion

Clearance (CL):	3.764
Half-life (T1/2):	0.15

ADMET: Toxicity

hERG Blockers:	0.324
Human Hepatotoxicity (H-HT):	0.884
Drug-inuced Liver Injury (DILI):	0.793
AMES Toxicity:	0.665
Rat Oral Acute Toxicity:	0.968
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.528
Carcinogencity:	0.906
Eye Corrosion:	0.004
Eye Irritation:	0.243
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC162484

Natural Product ID:	NPC162484
*Common Name:**	Koenimbine
IUPAC Name:	8-methoxy-3,3,5-trimethyl-11H-pyrano[3,2-a]carbazole
Synonyms:	Koenimbine
Standard InCHIKey:	OSERHKINMDLESD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H19NO2/c1-11-9-15-14-10-12(21-4)5-6-16(14)20-17(15)13-7-8-19(2,3)22-18(11)13/h5-10,20H,1-4H3
SMILES:	COc1ccc2c(c1)c1cc(C)c3c(c1[nH]2)C=CC(O3)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2323768
PubChem CID:	97487
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662104]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	Sri Lankan	n.a.	PMID[23376010]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	fruits	Coimbatore, India	2010-JUN	PMID[23691929]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27136692]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3364	Murraya koenigii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3364	Murraya koenigii	Species	Rutaceae	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	23

Activity Type	# Activity
Individual Protein	6
NON-MOLECULAR	2
Others	17

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	4.3	%	PMID[541909]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	1.0	%	PMID[541909]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	-0.1	%	PMID[541909]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	-1.0	%	PMID[541909]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	0.7	%	PMID[541909]
NPT2797	Individual Protein	Pancreatic lipase	Homo sapiens	IC50	=	168600.0	nM	PMID[541911]
NPT27	Others	Unspecified		Activity	=	37.9	%	PMID[541909]
NPT27	Others	Unspecified		Activity	=	66.6	%	PMID[541909]
NPT27	Others	Unspecified		Activity	=	92.4	%	PMID[541909]
NPT27	Others	Unspecified		Activity	=	114.4	%	PMID[541909]
NPT2	Others	Unspecified		IC50	=	1200.0	nM	PMID[541909]
NPT2	Others	Unspecified		Inhibition	=	86.2	%	PMID[541909]
NPT2	Others	Unspecified		Inhibition	=	77.0	%	PMID[541909]
NPT2	Others	Unspecified		Inhibition	=	42.5	%	PMID[541909]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	15.5	%	PMID[541910]
NPT27	Others	Unspecified		T1/2	=	2.205	hr	PMID[541910]
NPT27	Others	Unspecified		Stability	=	58.0	%	PMID[541910]
NPT610	Others	Molecular identity unknown		FC	=	1.44	n.a.	PMID[541910]
NPT610	Others	Molecular identity unknown		FC	=	1.41	n.a.	PMID[541910]
NPT610	Others	Molecular identity unknown		FC	=	2.54	n.a.	PMID[541910]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	19.8	%	PMID[541910]
NPT27	Others	Unspecified		K	=	0.005	/min	PMID[541910]
NPT27	Others	Unspecified		AUC	=	9.45	uM.hr	PMID[541910]
NPT27	Others	Unspecified		Cmax	=	1810.0	nM	PMID[541910]
NPT27	Others	Unspecified		Tmax	=	0.83	hr	PMID[541910]

☑ 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 NPC162484 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	679
0.1-0.2	4139
0.2-0.3	13253
0.3-0.4	5086
0.4-0.5	14179
0.5-0.6	3405
0.6-0.7	1479
0.7-0.8	362
0.8-0.85	65
0.85-0.9	24
0.9-0.95	19
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9722	High Similarity	NPC72211
0.9624	High Similarity	NPC201697
0.9611	High Similarity	NPC70259
0.9556	High Similarity	NPC43787
0.9556	High Similarity	NPC131017
0.9556	High Similarity	NPC205934
0.9471	High Similarity	NPC48353
0.9405	High Similarity	NPC475085
0.9405	High Similarity	NPC291535
0.9405	High Similarity	NPC475112
0.9255	High Similarity	NPC476106
0.9247	High Similarity	NPC267423
0.9206	High Similarity	NPC193777
0.9202	High Similarity	NPC470930
0.9144	High Similarity	NPC476044
0.9135	High Similarity	NPC70956
0.9135	High Similarity	NPC243834
0.8912	High Similarity	NPC209769
0.8911	High Similarity	NPC252251
0.8824	High Similarity	NPC477531
0.88	High Similarity	NPC477532
0.8775	High Similarity	NPC209174
0.875	High Similarity	NPC477533
0.873	High Similarity	NPC153042
0.8706	High Similarity	NPC198503
0.8641	High Similarity	NPC475253
0.8641	High Similarity	NPC84478
0.8614	High Similarity	NPC280799
0.8601	High Similarity	NPC135887
0.8601	High Similarity	NPC199277
0.8595	High Similarity	NPC94943
0.8594	High Similarity	NPC11017
0.8587	High Similarity	NPC176127
0.8557	High Similarity	NPC46561
0.8541	High Similarity	NPC190007
0.8524	High Similarity	NPC6786
0.8515	High Similarity	NPC473179
0.8497	Intermediate Similarity	NPC329747
0.8486	Intermediate Similarity	NPC212535
0.8477	Intermediate Similarity	NPC470931
0.8462	Intermediate Similarity	NPC223427
0.8457	Intermediate Similarity	NPC242928
0.836	Intermediate Similarity	NPC246700
0.8341	Intermediate Similarity	NPC277351
0.8333	Intermediate Similarity	NPC249583
0.8333	Intermediate Similarity	NPC4687
0.8325	Intermediate Similarity	NPC285558
0.8324	Intermediate Similarity	NPC88363
0.8317	Intermediate Similarity	NPC473185
0.8308	Intermediate Similarity	NPC310211
0.8308	Intermediate Similarity	NPC308137
0.8308	Intermediate Similarity	NPC329793
0.8293	Intermediate Similarity	NPC86078
0.8283	Intermediate Similarity	NPC45190
0.8283	Intermediate Similarity	NPC300156
0.8276	Intermediate Similarity	NPC170114
0.8259	Intermediate Similarity	NPC208284
0.8256	Intermediate Similarity	NPC128823
0.8235	Intermediate Similarity	NPC169402
0.8227	Intermediate Similarity	NPC470549
0.8227	Intermediate Similarity	NPC116238
0.8209	Intermediate Similarity	NPC199667
0.8204	Intermediate Similarity	NPC150239
0.82	Intermediate Similarity	NPC475910
0.8177	Intermediate Similarity	NPC478074
0.8168	Intermediate Similarity	NPC87413
0.8168	Intermediate Similarity	NPC128751
0.8159	Intermediate Similarity	NPC473181
0.8138	Intermediate Similarity	NPC474798
0.8128	Intermediate Similarity	NPC473180
0.8128	Intermediate Similarity	NPC94157
0.8125	Intermediate Similarity	NPC76748
0.8125	Intermediate Similarity	NPC106833
0.8125	Intermediate Similarity	NPC469497
0.8119	Intermediate Similarity	NPC11464
0.8119	Intermediate Similarity	NPC471304
0.8108	Intermediate Similarity	NPC474409
0.8107	Intermediate Similarity	NPC247803
0.8095	Intermediate Similarity	NPC227908
0.8093	Intermediate Similarity	NPC307963
0.8093	Intermediate Similarity	NPC475190
0.8083	Intermediate Similarity	NPC92111
0.8073	Intermediate Similarity	NPC296527
0.8068	Intermediate Similarity	NPC208084
0.8037	Intermediate Similarity	NPC473182
0.8029	Intermediate Similarity	NPC174760
0.8021	Intermediate Similarity	NPC66083
0.801	Intermediate Similarity	NPC13880
0.801	Intermediate Similarity	NPC251090
0.8009	Intermediate Similarity	NPC473183
0.799	Intermediate Similarity	NPC232727
0.7951	Intermediate Similarity	NPC316981
0.7941	Intermediate Similarity	NPC167860
0.7941	Intermediate Similarity	NPC123976
0.794	Intermediate Similarity	NPC176538
0.7937	Intermediate Similarity	NPC72980
0.7933	Intermediate Similarity	NPC473041
0.7933	Intermediate Similarity	NPC96321
0.7931	Intermediate Similarity	NPC39679
0.7925	Intermediate Similarity	NPC202503
0.7917	Intermediate Similarity	NPC473184
0.7913	Intermediate Similarity	NPC469592
0.7913	Intermediate Similarity	NPC471080
0.7913	Intermediate Similarity	NPC266931
0.788	Intermediate Similarity	NPC473187
0.7877	Intermediate Similarity	NPC179287
0.7876	Intermediate Similarity	NPC204385
0.7872	Intermediate Similarity	NPC312872
0.7857	Intermediate Similarity	NPC132642
0.7857	Intermediate Similarity	NPC26850
0.7847	Intermediate Similarity	NPC469594
0.7837	Intermediate Similarity	NPC3207
0.7824	Intermediate Similarity	NPC473189
0.7816	Intermediate Similarity	NPC23294
0.781	Intermediate Similarity	NPC213530
0.781	Intermediate Similarity	NPC193267
0.7799	Intermediate Similarity	NPC314552
0.7783	Intermediate Similarity	NPC144452
0.7783	Intermediate Similarity	NPC280272
0.7773	Intermediate Similarity	NPC225279
0.7767	Intermediate Similarity	NPC303951
0.7766	Intermediate Similarity	NPC114335
0.7766	Intermediate Similarity	NPC99666
0.7766	Intermediate Similarity	NPC280964
0.7766	Intermediate Similarity	NPC141915
0.7751	Intermediate Similarity	NPC148183
0.7751	Intermediate Similarity	NPC152768
0.774	Intermediate Similarity	NPC39500
0.7736	Intermediate Similarity	NPC310118
0.7729	Intermediate Similarity	NPC9894
0.7729	Intermediate Similarity	NPC187501
0.7714	Intermediate Similarity	NPC305984
0.7696	Intermediate Similarity	NPC474688
0.7692	Intermediate Similarity	NPC26872
0.7685	Intermediate Similarity	NPC274640
0.7678	Intermediate Similarity	NPC303658
0.7673	Intermediate Similarity	NPC121772
0.767	Intermediate Similarity	NPC86834
0.767	Intermediate Similarity	NPC210828
0.7668	Intermediate Similarity	NPC206201
0.7644	Intermediate Similarity	NPC288943
0.7604	Intermediate Similarity	NPC283152
0.76	Intermediate Similarity	NPC475666
0.7598	Intermediate Similarity	NPC295898
0.7594	Intermediate Similarity	NPC184408
0.7586	Intermediate Similarity	NPC315957
0.7586	Intermediate Similarity	NPC249040
0.7585	Intermediate Similarity	NPC476465
0.7573	Intermediate Similarity	NPC472111
0.7563	Intermediate Similarity	NPC46580
0.7558	Intermediate Similarity	NPC110151
0.7556	Intermediate Similarity	NPC81939
0.755	Intermediate Similarity	NPC279401
0.755	Intermediate Similarity	NPC79293
0.7546	Intermediate Similarity	NPC21638
0.7543	Intermediate Similarity	NPC89549
0.7524	Intermediate Similarity	NPC16452
0.7524	Intermediate Similarity	NPC476581
0.7524	Intermediate Similarity	NPC294620
0.7524	Intermediate Similarity	NPC36229
0.7523	Intermediate Similarity	NPC311906
0.7523	Intermediate Similarity	NPC471762
0.7513	Intermediate Similarity	NPC61350
0.75	Intermediate Similarity	NPC475844
0.75	Intermediate Similarity	NPC477066
0.75	Intermediate Similarity	NPC211416
0.75	Intermediate Similarity	NPC62069
0.75	Intermediate Similarity	NPC474192
0.75	Intermediate Similarity	NPC475720
0.7489	Intermediate Similarity	NPC131486
0.7488	Intermediate Similarity	NPC60621
0.7477	Intermediate Similarity	NPC478078
0.7477	Intermediate Similarity	NPC157931
0.7476	Intermediate Similarity	NPC469440
0.7467	Intermediate Similarity	NPC478082
0.7467	Intermediate Similarity	NPC477067
0.7467	Intermediate Similarity	NPC473540
0.7467	Intermediate Similarity	NPC478081
0.7464	Intermediate Similarity	NPC469589
0.7463	Intermediate Similarity	NPC106937
0.7462	Intermediate Similarity	NPC314002
0.7461	Intermediate Similarity	NPC56618
0.7452	Intermediate Similarity	NPC321428
0.7451	Intermediate Similarity	NPC18487
0.745	Intermediate Similarity	NPC469390
0.7442	Intermediate Similarity	NPC472099
0.7441	Intermediate Similarity	NPC251160
0.7441	Intermediate Similarity	NPC202768
0.7441	Intermediate Similarity	NPC53069
0.7441	Intermediate Similarity	NPC26679
0.7441	Intermediate Similarity	NPC296482
0.7441	Intermediate Similarity	NPC264176
0.7432	Intermediate Similarity	NPC39370
0.7431	Intermediate Similarity	NPC200888
0.7426	Intermediate Similarity	NPC326634
0.7426	Intermediate Similarity	NPC276517
0.7424	Intermediate Similarity	NPC160381
0.7424	Intermediate Similarity	NPC171171
0.7421	Intermediate Similarity	NPC473186
0.7419	Intermediate Similarity	NPC51388

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 NPC162484 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	407
0.1-0.2	717
0.2-0.3	857
0.3-0.4	1539
0.4-0.5	2746
0.5-0.6	2030
0.6-0.7	707
0.7-0.8	137
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD5658	Approved
0.8469	Intermediate Similarity	NPD3003	Approved
0.8446	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.8238	Intermediate Similarity	NPD4418	Discontinued
0.8227	Intermediate Similarity	NPD5903	Approved
0.8227	Intermediate Similarity	NPD5902	Approved
0.8187	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1768	Approved
0.8093	Intermediate Similarity	NPD1038	Approved
0.801	Intermediate Similarity	NPD5612	Discontinued
0.797	Intermediate Similarity	NPD7222	Phase 2
0.797	Intermediate Similarity	NPD7453	Approved
0.797	Intermediate Similarity	NPD7452	Approved
0.7943	Intermediate Similarity	NPD5930	Phase 3
0.7933	Intermediate Similarity	NPD6985	Discontinued
0.7895	Intermediate Similarity	NPD7194	Discontinued
0.7889	Intermediate Similarity	NPD3825	Phase 3
0.7882	Intermediate Similarity	NPD1392	Approved
0.7847	Intermediate Similarity	NPD5632	Approved
0.7842	Intermediate Similarity	NPD3920	Phase 2
0.7799	Intermediate Similarity	NPD5164	Discontinued
0.7788	Intermediate Similarity	NPD7558	Phase 2
0.7778	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD8403	Phase 1
0.7716	Intermediate Similarity	NPD5913	Phase 3
0.7716	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD4795	Phase 2
0.7689	Intermediate Similarity	NPD6242	Discontinued
0.7685	Intermediate Similarity	NPD5559	Phase 2
0.768	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD5067	Phase 2
0.7644	Intermediate Similarity	NPD5066	Phase 2
0.7638	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD6494	Phase 2
0.7586	Intermediate Similarity	NPD1739	Approved
0.7586	Intermediate Similarity	NPD1740	Approved
0.7585	Intermediate Similarity	NPD2187	Approved
0.7585	Intermediate Similarity	NPD2189	Approved
0.756	Intermediate Similarity	NPD6220	Phase 3
0.7551	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD4511	Phase 1
0.7512	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD5530	Phase 1
0.7467	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD802	Phase 2
0.7442	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7441	Intermediate Similarity	NPD3816	Phase 1
0.7441	Intermediate Similarity	NPD3815	Phase 1
0.7438	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6590	Discontinued
0.7424	Intermediate Similarity	NPD6244	Phase 3
0.7424	Intermediate Similarity	NPD5256	Discontinued
0.7424	Intermediate Similarity	NPD6243	Phase 3
0.7413	Intermediate Similarity	NPD3923	Approved
0.7413	Intermediate Similarity	NPD3924	Approved
0.7413	Intermediate Similarity	NPD3921	Approved
0.7413	Intermediate Similarity	NPD3922	Approved
0.7401	Intermediate Similarity	NPD4349	Approved
0.7401	Intermediate Similarity	NPD4350	Approved
0.7398	Intermediate Similarity	NPD4204	Approved
0.7398	Intermediate Similarity	NPD4203	Approved
0.7395	Intermediate Similarity	NPD3875	Discontinued
0.7389	Intermediate Similarity	NPD5512	Phase 3
0.7378	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5429	Discontinued
0.7358	Intermediate Similarity	NPD7069	Discontinued
0.7354	Intermediate Similarity	NPD6964	Approved
0.7354	Intermediate Similarity	NPD6963	Approved
0.7353	Intermediate Similarity	NPD5003	Discontinued
0.7344	Intermediate Similarity	NPD1326	Approved
0.7344	Intermediate Similarity	NPD1325	Approved
0.7343	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4885	Approved
0.734	Intermediate Similarity	NPD6251	Discontinued
0.7336	Intermediate Similarity	NPD8358	Approved
0.7325	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD8364	Approved
0.7322	Intermediate Similarity	NPD8363	Approved
0.7321	Intermediate Similarity	NPD6150	Discontinued
0.7315	Intermediate Similarity	NPD3402	Phase 1
0.7311	Intermediate Similarity	NPD4502	Phase 2
0.7304	Intermediate Similarity	NPD6550	Discontinued
0.7302	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4996	Approved
0.7297	Intermediate Similarity	NPD4995	Approved
0.7294	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3397	Phase 2
0.7273	Intermediate Similarity	NPD5482	Discontinued
0.7268	Intermediate Similarity	NPD1305	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7948	Phase 1
0.7261	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD4925	Approved
0.7252	Intermediate Similarity	NPD4952	Phase 3
0.7249	Intermediate Similarity	NPD6230	Discontinued
0.7238	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6473	Phase 1
0.7235	Intermediate Similarity	NPD3763	Approved
0.7215	Intermediate Similarity	NPD7221	Approved
0.7215	Intermediate Similarity	NPD1954	Phase 1
0.7215	Intermediate Similarity	NPD7219	Approved
0.7213	Intermediate Similarity	NPD8465	Approved
0.7213	Intermediate Similarity	NPD8429	Approved
0.7213	Intermediate Similarity	NPD8467	Approved
0.7213	Intermediate Similarity	NPD8466	Approved
0.7213	Intermediate Similarity	NPD8427	Approved
0.7213	Intermediate Similarity	NPD8428	Approved
0.7203	Intermediate Similarity	NPD7955	Approved
0.7203	Intermediate Similarity	NPD7956	Approved
0.7202	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4889	Approved
0.7195	Intermediate Similarity	NPD7050	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7051	Phase 3
0.7192	Intermediate Similarity	NPD2334	Discontinued
0.7184	Intermediate Similarity	NPD6988	Phase 1
0.7177	Intermediate Similarity	NPD6208	Discontinued
0.7166	Intermediate Similarity	NPD814	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4875	Phase 3
0.7162	Intermediate Similarity	NPD4876	Phase 3
0.7157	Intermediate Similarity	NPD6569	Phase 2
0.7156	Intermediate Similarity	NPD4373	Phase 2
0.715	Intermediate Similarity	NPD5416	Discontinued
0.7149	Intermediate Similarity	NPD5905	Phase 1
0.7149	Intermediate Similarity	NPD7719	Discontinued
0.7149	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6324	Phase 1
0.7143	Intermediate Similarity	NPD2564	Approved
0.7143	Intermediate Similarity	NPD2565	Phase 2
0.7143	Intermediate Similarity	NPD6962	Phase 2
0.7136	Intermediate Similarity	NPD6736	Discontinued
0.713	Intermediate Similarity	NPD3257	Approved
0.713	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7555	Discontinued
0.7129	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5680	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6790	Phase 1
0.7116	Intermediate Similarity	NPD6202	Discontinued
0.7115	Intermediate Similarity	NPD8395	Approved
0.7115	Intermediate Similarity	NPD8396	Approved
0.7109	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2952	Discontinued
0.7098	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD8512	Phase 3
0.7097	Intermediate Similarity	NPD8426	Approved
0.7097	Intermediate Similarity	NPD8460	Approved
0.7097	Intermediate Similarity	NPD8425	Approved
0.7097	Intermediate Similarity	NPD8459	Approved
0.7095	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4439	Discontinued
0.7089	Intermediate Similarity	NPD2916	Discontinued
0.7078	Intermediate Similarity	NPD3258	Approved
0.7075	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD3440	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6742	Phase 2
0.7064	Intermediate Similarity	NPD6743	Phase 2
0.7056	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7592	Phase 2
0.7054	Intermediate Similarity	NPD7803	Approved
0.7044	Intermediate Similarity	NPD2749	Discontinued
0.7033	Intermediate Similarity	NPD3814	Phase 1
0.7032	Intermediate Similarity	NPD3354	Phase 2
0.7026	Intermediate Similarity	NPD4986	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD1900	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5051	Phase 1
0.7009	Intermediate Similarity	NPD7672	Approved
0.7009	Intermediate Similarity	NPD7671	Approved
0.7005	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5944	Phase 1
0.7005	Intermediate Similarity	NPD5945	Phase 1
0.6996	Remote Similarity	NPD5488	Discontinued
0.6996	Remote Similarity	NPD6246	Approved
0.6991	Remote Similarity	NPD5936	Approved
0.6991	Remote Similarity	NPD5939	Approved
0.6985	Remote Similarity	NPD5810	Discontinued
0.6985	Remote Similarity	NPD3503	Approved
0.6985	Remote Similarity	NPD3504	Approved
0.6981	Remote Similarity	NPD6991	Approved
0.6978	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4437	Phase 3
0.6971	Remote Similarity	NPD774	Phase 3
0.6959	Remote Similarity	NPD4927	Discontinued
0.6959	Remote Similarity	NPD3330	Phase 1
0.6958	Remote Similarity	NPD6530	Approved
0.6958	Remote Similarity	NPD6531	Approved
0.6955	Remote Similarity	NPD7395	Discontinued
0.695	Remote Similarity	NPD7479	Phase 2
0.6948	Remote Similarity	NPD4037	Approved
0.6948	Remote Similarity	NPD4038	Approved
0.6948	Remote Similarity	NPD32	Approved
0.6948	Remote Similarity	NPD4035	Approved
0.6948	Remote Similarity	NPD4033	Approved
0.6948	Remote Similarity	NPD4039	Approved
0.6948	Remote Similarity	NPD31	Approved
0.6948	Remote Similarity	NPD4034	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