NPASS Compound

Structure

NPC281513 OpenBabel07101718232D 21 22 0 0 0 0 0 0 0 0999 V2000 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 21 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 10 2 0 0 0 0 6 11 1 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 14 1 0 0 0 0 9 11 2 0 0 0 0 9 13 1 0 0 0 0 11 17 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 19 2 0 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.12
Volume:	302.181
LogP:	4.792
LogD:	3.447
LogS:	-3.534
# Rotatable Bonds:	3
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.59
Synthetic Accessibility Score:	2.879
Fsp3:	0.176
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:	-4.941
MDCK Permeability:	1.5926201740512624e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.248
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.044
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	98.28594207763672%
Volume Distribution (VD):	0.632
Pgp-substrate:	5.354629993438721%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.953
CYP2C19-inhibitor:	0.261
CYP2C19-substrate:	0.309
CYP2C9-inhibitor:	0.506
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.671
CYP2D6-substrate:	0.926
CYP3A4-inhibitor:	0.113
CYP3A4-substrate:	0.285

ADMET: Excretion

Clearance (CL):	7.509
Half-life (T1/2):	0.708

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.171
Drug-inuced Liver Injury (DILI):	0.495
AMES Toxicity:	0.82
Rat Oral Acute Toxicity:	0.781
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.959
Carcinogencity:	0.596
Eye Corrosion:	0.094
Eye Irritation:	0.953
Respiratory Toxicity:	0.878

Download Data

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

Natural Product: NPC281513

Natural Product ID:	NPC281513
*Common Name:**	8-O-Methyl-11-Deoxyalkannin
IUPAC Name:	5-hydroxy-8-methoxy-2-(4-methylpent-3-enyl)naphthalene-1,4-dione
Synonyms:
Standard InCHIKey:	OVTNFJRJFLMYCD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H18O4/c1-10(2)5-4-6-11-9-13(19)15-12(18)7-8-14(21-3)16(15)17(11)20/h5,7-9,18H,4,6H2,1-3H3
SMILES:	COc1ccc(c2c1C(=O)C(=CC2=O)CCC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097731
PubChem CID:	46833120
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO12855	Alkanna cappadocica	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20405844]
NPO12855	Alkanna cappadocica	Species	Boraginaceae	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	14

Activity Type	# Activity
Cell Line	13
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	5980.0	nM	PMID[449795]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	5110.0	nM	PMID[449795]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	7480.0	nM	PMID[449795]
NPT2296	Cell Line	AU565	Homo sapiens	IC50	=	7080.0	nM	PMID[449795]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	8050.0	nM	PMID[449795]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	11080.0	nM	PMID[449795]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	11890.0	nM	PMID[449795]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	6380.0	nM	PMID[449795]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	6520.0	nM	PMID[449795]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	12050.0	nM	PMID[449795]
NPT2405	Cell Line	SAOS-2	Homo sapiens	IC50	=	12510.0	nM	PMID[449795]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	6390.0	nM	PMID[449795]
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	=	6570.0	nM	PMID[449795]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	24490.0	nM	PMID[449795]

☑ 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 NPC281513 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	331
0.1-0.2	1524
0.2-0.3	3776
0.3-0.4	9948
0.4-0.5	8580
0.5-0.6	4012
0.6-0.7	7983
0.7-0.8	5940
0.8-0.85	501
0.85-0.9	90
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC22222
0.9375	High Similarity	NPC45537
0.9343	High Similarity	NPC89664
0.9343	High Similarity	NPC274085
0.9297	High Similarity	NPC306765
0.9265	High Similarity	NPC124365
0.9259	High Similarity	NPC477408
0.9237	High Similarity	NPC205360
0.9203	High Similarity	NPC477409
0.9062	High Similarity	NPC182646
0.9037	High Similarity	NPC141934
0.9023	High Similarity	NPC246693
0.9023	High Similarity	NPC242358
0.9023	High Similarity	NPC110609
0.8978	High Similarity	NPC29771
0.8978	High Similarity	NPC1268
0.8978	High Similarity	NPC299405
0.8978	High Similarity	NPC476477
0.8978	High Similarity	NPC111422
0.8978	High Similarity	NPC306835
0.8978	High Similarity	NPC256463
0.8978	High Similarity	NPC216312
0.8978	High Similarity	NPC471602
0.8936	High Similarity	NPC300540
0.8921	High Similarity	NPC329493
0.8913	High Similarity	NPC147542
0.8913	High Similarity	NPC42262
0.8913	High Similarity	NPC32749
0.8913	High Similarity	NPC220496
0.8913	High Similarity	NPC37992
0.8913	High Similarity	NPC327916
0.8913	High Similarity	NPC241349
0.8881	High Similarity	NPC118253
0.8864	High Similarity	NPC237225
0.8857	High Similarity	NPC476473
0.8849	High Similarity	NPC257003
0.8849	High Similarity	NPC471444
0.8832	High Similarity	NPC301341
0.8788	High Similarity	NPC470841
0.8788	High Similarity	NPC471530
0.8786	High Similarity	NPC69755
0.8786	High Similarity	NPC474300
0.8759	High Similarity	NPC232996
0.875	High Similarity	NPC206778
0.875	High Similarity	NPC285829
0.8741	High Similarity	NPC477406
0.8732	High Similarity	NPC478019
0.8731	High Similarity	NPC198305
0.8714	High Similarity	NPC84273
0.8712	High Similarity	NPC96915
0.8712	High Similarity	NPC51037
0.8702	High Similarity	NPC310540
0.8702	High Similarity	NPC4012
0.8696	High Similarity	NPC284184
0.8692	High Similarity	NPC307174
0.8672	High Similarity	NPC232178
0.8667	High Similarity	NPC141549
0.8667	High Similarity	NPC477412
0.8657	High Similarity	NPC57552
0.8647	High Similarity	NPC71525
0.8613	High Similarity	NPC1249
0.8603	High Similarity	NPC251549
0.8603	High Similarity	NPC474340
0.8593	High Similarity	NPC7569
0.8593	High Similarity	NPC278787
0.8592	High Similarity	NPC53016
0.8591	High Similarity	NPC67197
0.8571	High Similarity	NPC3224
0.8571	High Similarity	NPC227741
0.8571	High Similarity	NPC295339
0.8571	High Similarity	NPC49647
0.8571	High Similarity	NPC1991
0.8571	High Similarity	NPC470407
0.8571	High Similarity	NPC136342
0.8571	High Similarity	NPC295202
0.8571	High Similarity	NPC231774
0.8562	High Similarity	NPC294646
0.8561	High Similarity	NPC56332
0.8561	High Similarity	NPC471542
0.855	High Similarity	NPC49441
0.8542	High Similarity	NPC60389
0.8542	High Similarity	NPC211565
0.854	High Similarity	NPC171968
0.8531	High Similarity	NPC475201
0.8529	High Similarity	NPC205992
0.8521	High Similarity	NPC49108
0.8519	High Similarity	NPC34414
0.8519	High Similarity	NPC278928
0.8519	High Similarity	NPC146647
0.8516	High Similarity	NPC269414
0.8503	High Similarity	NPC144283
0.85	High Similarity	NPC61590
0.85	High Similarity	NPC475104
0.8496	Intermediate Similarity	NPC131799
0.8496	Intermediate Similarity	NPC224657
0.8489	Intermediate Similarity	NPC272268
0.8485	Intermediate Similarity	NPC375356
0.8485	Intermediate Similarity	NPC477153
0.8483	Intermediate Similarity	NPC478018
0.8478	Intermediate Similarity	NPC27394
0.8472	Intermediate Similarity	NPC160777
0.8472	Intermediate Similarity	NPC73416
0.8467	Intermediate Similarity	NPC309430
0.8467	Intermediate Similarity	NPC470160
0.8456	Intermediate Similarity	NPC3898
0.8456	Intermediate Similarity	NPC55949
0.8456	Intermediate Similarity	NPC475741
0.8451	Intermediate Similarity	NPC149780
0.845	Intermediate Similarity	NPC171023
0.8444	Intermediate Similarity	NPC165257
0.8444	Intermediate Similarity	NPC48248
0.8438	Intermediate Similarity	NPC477453
0.8438	Intermediate Similarity	NPC108288
0.8429	Intermediate Similarity	NPC305060
0.8429	Intermediate Similarity	NPC477534
0.8429	Intermediate Similarity	NPC245923
0.8425	Intermediate Similarity	NPC172329
0.8425	Intermediate Similarity	NPC2569
0.8425	Intermediate Similarity	NPC5537
0.8421	Intermediate Similarity	NPC234890
0.8421	Intermediate Similarity	NPC74507
0.8417	Intermediate Similarity	NPC22644
0.8409	Intermediate Similarity	NPC300274
0.8403	Intermediate Similarity	NPC103910
0.8403	Intermediate Similarity	NPC19896
0.84	Intermediate Similarity	NPC279605
0.84	Intermediate Similarity	NPC469507
0.8394	Intermediate Similarity	NPC85342
0.8394	Intermediate Similarity	NPC244699
0.8392	Intermediate Similarity	NPC11314
0.8389	Intermediate Similarity	NPC477691
0.8389	Intermediate Similarity	NPC135522
0.8389	Intermediate Similarity	NPC290927
0.8389	Intermediate Similarity	NPC155686
0.8382	Intermediate Similarity	NPC206028
0.838	Intermediate Similarity	NPC477537
0.8378	Intermediate Similarity	NPC46882
0.8378	Intermediate Similarity	NPC132990
0.837	Intermediate Similarity	NPC298884
0.8369	Intermediate Similarity	NPC173980
0.8369	Intermediate Similarity	NPC98395
0.8359	Intermediate Similarity	NPC240163
0.8358	Intermediate Similarity	NPC103540
0.8357	Intermediate Similarity	NPC472881
0.8357	Intermediate Similarity	NPC155211
0.8357	Intermediate Similarity	NPC474813
0.8357	Intermediate Similarity	NPC475549
0.8356	Intermediate Similarity	NPC126767
0.8356	Intermediate Similarity	NPC118027
0.8356	Intermediate Similarity	NPC190648
0.8356	Intermediate Similarity	NPC289042
0.8356	Intermediate Similarity	NPC312929
0.8356	Intermediate Similarity	NPC245584
0.8356	Intermediate Similarity	NPC56433
0.8356	Intermediate Similarity	NPC252208
0.8355	Intermediate Similarity	NPC284495
0.8346	Intermediate Similarity	NPC135062
0.8345	Intermediate Similarity	NPC473951
0.8345	Intermediate Similarity	NPC274876
0.8345	Intermediate Similarity	NPC28632
0.8345	Intermediate Similarity	NPC474630
0.8344	Intermediate Similarity	NPC44199
0.8333	Intermediate Similarity	NPC312560
0.8333	Intermediate Similarity	NPC316691
0.8333	Intermediate Similarity	NPC21873
0.8333	Intermediate Similarity	NPC88864
0.8333	Intermediate Similarity	NPC58685
0.8322	Intermediate Similarity	NPC477690
0.8322	Intermediate Similarity	NPC164912
0.8322	Intermediate Similarity	NPC145673
0.8322	Intermediate Similarity	NPC283292
0.8322	Intermediate Similarity	NPC470340
0.8322	Intermediate Similarity	NPC281272
0.8321	Intermediate Similarity	NPC136588
0.8321	Intermediate Similarity	NPC199253
0.8311	Intermediate Similarity	NPC255641
0.8311	Intermediate Similarity	NPC290954
0.8311	Intermediate Similarity	NPC147735
0.8311	Intermediate Similarity	NPC227122
0.8311	Intermediate Similarity	NPC470568
0.831	Intermediate Similarity	NPC223336
0.8309	Intermediate Similarity	NPC201419
0.8309	Intermediate Similarity	NPC282923
0.8299	Intermediate Similarity	NPC55327
0.8299	Intermediate Similarity	NPC216624
0.8298	Intermediate Similarity	NPC98804
0.8286	Intermediate Similarity	NPC283088
0.8284	Intermediate Similarity	NPC152525
0.8284	Intermediate Similarity	NPC68756
0.8284	Intermediate Similarity	NPC470162
0.8284	Intermediate Similarity	NPC142956
0.8284	Intermediate Similarity	NPC470163
0.8276	Intermediate Similarity	NPC475813
0.8276	Intermediate Similarity	NPC471600
0.8273	Intermediate Similarity	NPC477536
0.8273	Intermediate Similarity	NPC193169
0.8273	Intermediate Similarity	NPC254603
0.8273	Intermediate Similarity	NPC59459
0.8273	Intermediate Similarity	NPC53896
0.8273	Intermediate Similarity	NPC115458

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 NPC281513 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	979
0.2-0.3	1404
0.3-0.4	2532
0.4-0.5	1988
0.5-0.6	1247
0.6-0.7	549
0.7-0.8	144
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8696	High Similarity	NPD2935	Discontinued
0.85	High Similarity	NPD2346	Discontinued
0.8438	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8358	Intermediate Similarity	NPD1470	Approved
0.8243	Intermediate Similarity	NPD3226	Approved
0.8162	Intermediate Similarity	NPD2798	Approved
0.8099	Intermediate Similarity	NPD2799	Discontinued
0.806	Intermediate Similarity	NPD1201	Approved
0.8058	Intermediate Similarity	NPD2313	Discontinued
0.7986	Intermediate Similarity	NPD2344	Approved
0.7852	Intermediate Similarity	NPD2533	Approved
0.7852	Intermediate Similarity	NPD2534	Approved
0.7852	Intermediate Similarity	NPD2532	Approved
0.7832	Intermediate Similarity	NPD1607	Approved
0.7823	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD1240	Approved
0.7808	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6232	Discontinued
0.7778	Intermediate Similarity	NPD4626	Approved
0.777	Intermediate Similarity	NPD2309	Approved
0.7762	Intermediate Similarity	NPD447	Suspended
0.7754	Intermediate Similarity	NPD1876	Approved
0.775	Intermediate Similarity	NPD7473	Discontinued
0.7744	Intermediate Similarity	NPD9493	Approved
0.774	Intermediate Similarity	NPD1471	Phase 3
0.7737	Intermediate Similarity	NPD9717	Approved
0.7733	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1510	Phase 2
0.7704	Intermediate Similarity	NPD1651	Approved
0.7703	Intermediate Similarity	NPD7003	Approved
0.7698	Intermediate Similarity	NPD1203	Approved
0.7677	Intermediate Similarity	NPD2801	Approved
0.7677	Intermediate Similarity	NPD7819	Suspended
0.7676	Intermediate Similarity	NPD411	Approved
0.7664	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD1283	Approved
0.7619	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6844	Discontinued
0.7609	Intermediate Similarity	NPD3972	Approved
0.76	Intermediate Similarity	NPD3300	Phase 2
0.7584	Intermediate Similarity	NPD3750	Approved
0.7564	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD6671	Approved
0.7535	Intermediate Similarity	NPD6832	Phase 2
0.7532	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2800	Approved
0.7517	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6959	Discontinued
0.7484	Intermediate Similarity	NPD4380	Phase 2
0.7467	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD3496	Discontinued
0.745	Intermediate Similarity	NPD1549	Phase 2
0.7445	Intermediate Similarity	NPD5691	Approved
0.7432	Intermediate Similarity	NPD5406	Approved
0.7432	Intermediate Similarity	NPD5405	Approved
0.7432	Intermediate Similarity	NPD5408	Approved
0.7432	Intermediate Similarity	NPD5404	Approved
0.7432	Intermediate Similarity	NPD1551	Phase 2
0.7429	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1281	Approved
0.7405	Intermediate Similarity	NPD5402	Approved
0.74	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2932	Approved
0.7389	Intermediate Similarity	NPD1934	Approved
0.7388	Intermediate Similarity	NPD1241	Discontinued
0.7386	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4308	Phase 3
0.7358	Intermediate Similarity	NPD3882	Suspended
0.7347	Intermediate Similarity	NPD6651	Approved
0.7343	Intermediate Similarity	NPD9494	Approved
0.7338	Intermediate Similarity	NPD6273	Approved
0.7329	Intermediate Similarity	NPD5494	Approved
0.7329	Intermediate Similarity	NPD2979	Phase 3
0.7324	Intermediate Similarity	NPD2797	Approved
0.7321	Intermediate Similarity	NPD8312	Approved
0.7321	Intermediate Similarity	NPD8313	Approved
0.732	Intermediate Similarity	NPD7390	Discontinued
0.732	Intermediate Similarity	NPD1511	Approved
0.7315	Intermediate Similarity	NPD2796	Approved
0.731	Intermediate Similarity	NPD3268	Approved
0.731	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3764	Approved
0.7308	Intermediate Similarity	NPD7458	Discontinued
0.7305	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1611	Approved
0.7273	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1019	Discontinued
0.7266	Intermediate Similarity	NPD3019	Approved
0.7259	Intermediate Similarity	NPD1398	Phase 1
0.7254	Intermediate Similarity	NPD6696	Suspended
0.725	Intermediate Similarity	NPD7768	Phase 2
0.7248	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3748	Approved
0.7239	Intermediate Similarity	NPD5710	Approved
0.7239	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5711	Approved
0.7237	Intermediate Similarity	NPD4628	Phase 3
0.7229	Intermediate Similarity	NPD5844	Phase 1
0.7226	Intermediate Similarity	NPD7340	Approved
0.7226	Intermediate Similarity	NPD1512	Approved
0.7215	Intermediate Similarity	NPD7411	Suspended
0.7211	Intermediate Similarity	NPD4060	Phase 1
0.7211	Intermediate Similarity	NPD943	Approved
0.7205	Intermediate Similarity	NPD3749	Approved
0.7205	Intermediate Similarity	NPD7075	Discontinued
0.7203	Intermediate Similarity	NPD1164	Approved
0.72	Intermediate Similarity	NPD6099	Approved
0.72	Intermediate Similarity	NPD6100	Approved
0.7197	Intermediate Similarity	NPD2651	Approved
0.7197	Intermediate Similarity	NPD2649	Approved
0.7194	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2296	Approved
0.7185	Intermediate Similarity	NPD7635	Approved
0.7152	Intermediate Similarity	NPD6599	Discontinued
0.7143	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD74	Approved
0.7143	Intermediate Similarity	NPD2182	Approved
0.7143	Intermediate Similarity	NPD9266	Approved
0.7135	Intermediate Similarity	NPD6779	Approved
0.7135	Intermediate Similarity	NPD6777	Approved
0.7135	Intermediate Similarity	NPD6781	Approved
0.7135	Intermediate Similarity	NPD6778	Approved
0.7135	Intermediate Similarity	NPD6780	Approved
0.7135	Intermediate Similarity	NPD6776	Approved
0.7135	Intermediate Similarity	NPD6782	Approved
0.7133	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD8166	Discontinued
0.7113	Intermediate Similarity	NPD1608	Approved
0.7113	Intermediate Similarity	NPD1481	Phase 2
0.7101	Intermediate Similarity	NPD6559	Discontinued
0.7099	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD164	Approved
0.7097	Intermediate Similarity	NPD6799	Approved
0.7095	Intermediate Similarity	NPD4307	Phase 2
0.7093	Intermediate Similarity	NPD8150	Discontinued
0.7086	Intermediate Similarity	NPD4477	Approved
0.7086	Intermediate Similarity	NPD4476	Approved
0.7075	Intermediate Similarity	NPD7985	Registered
0.7068	Intermediate Similarity	NPD9267	Approved
0.7068	Intermediate Similarity	NPD9263	Approved
0.7068	Intermediate Similarity	NPD9264	Approved
0.7066	Intermediate Similarity	NPD3818	Discontinued
0.7051	Intermediate Similarity	NPD4662	Approved
0.7051	Intermediate Similarity	NPD4661	Approved
0.705	Intermediate Similarity	NPD5536	Phase 2
0.7048	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6166	Phase 2
0.7047	Intermediate Similarity	NPD1933	Approved
0.7042	Intermediate Similarity	NPD1535	Discovery
0.7034	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8032	Phase 2
0.7025	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1778	Approved
0.7017	Intermediate Similarity	NPD7696	Phase 3
0.7017	Intermediate Similarity	NPD7697	Approved
0.7017	Intermediate Similarity	NPD7698	Approved
0.7017	Intermediate Similarity	NPD7435	Discontinued
0.7007	Intermediate Similarity	NPD4625	Phase 3
0.7	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9545	Approved
0.6994	Remote Similarity	NPD8434	Phase 2
0.6993	Remote Similarity	NPD2233	Approved
0.6993	Remote Similarity	NPD2232	Approved
0.6993	Remote Similarity	NPD2230	Approved
0.6986	Remote Similarity	NPD2861	Phase 2
0.6978	Remote Similarity	NPD7871	Phase 2
0.6978	Remote Similarity	NPD7870	Phase 2
0.6975	Remote Similarity	NPD3817	Phase 2
0.6975	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2438	Suspended
0.6974	Remote Similarity	NPD2531	Phase 2
0.697	Remote Similarity	NPD1247	Approved
0.6968	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3266	Approved
0.6966	Remote Similarity	NPD3267	Approved
0.6964	Remote Similarity	NPD3751	Discontinued
0.6964	Remote Similarity	NPD7177	Discontinued
0.6962	Remote Similarity	NPD5403	Approved
0.6962	Remote Similarity	NPD920	Approved
0.6961	Remote Similarity	NPD6823	Phase 2
0.6957	Remote Similarity	NPD6801	Discontinued
0.6957	Remote Similarity	NPD6279	Approved
0.6957	Remote Similarity	NPD6280	Approved
0.6946	Remote Similarity	NPD6894	Phase 1
0.6944	Remote Similarity	NPD4749	Approved
0.6941	Remote Similarity	NPD5953	Discontinued
0.6937	Remote Similarity	NPD7028	Phase 2
0.6933	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6355	Discontinued
0.6918	Remote Similarity	NPD5647	Approved
0.6912	Remote Similarity	NPD2181	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