NPASS Compound

Structure

CID1249 OpenBabel06191715322D 21 23 0 0 0 0 0 0 0 0999 V2000 -3.4641 -2.0000 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 1.5000 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 -2.0000 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 -1.7321 -2.0000 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 -2.5981 -1.5000 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 -0.8660 -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 -1.7321 0.0000 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 -0.8660 -0.5000 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 0.0000 0.0000 0.0000 C 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 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 10 1 0 0 0 0 6 12 2 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 9 1 0 0 0 0 8 13 2 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 15 17 1 0 0 0 0 16 18 2 0 0 0 0 17 19 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	282.09
Volume:	290.988
LogP:	3.387
LogD:	3.045
LogS:	-5.712
# Rotatable Bonds:	2
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.725
Synthetic Accessibility Score:	2.03
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.788
MDCK Permeability:	3.399768320377916e-05
Pgp-inhibitor:	0.388
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.729

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.395
Plasma Protein Binding (PPB):	94.24629211425781%
Volume Distribution (VD):	0.518
Pgp-substrate:	2.120997905731201%

ADMET: Metabolism

CYP1A2-inhibitor:	0.934
CYP1A2-substrate:	0.939
CYP2C19-inhibitor:	0.656
CYP2C19-substrate:	0.441
CYP2C9-inhibitor:	0.736
CYP2C9-substrate:	0.861
CYP2D6-inhibitor:	0.099
CYP2D6-substrate:	0.847
CYP3A4-inhibitor:	0.806
CYP3A4-substrate:	0.41

ADMET: Excretion

Clearance (CL):	9.407
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.124
Drug-inuced Liver Injury (DILI):	0.913
AMES Toxicity:	0.791
Rat Oral Acute Toxicity:	0.183
Maximum Recommended Daily Dose:	0.817
Skin Sensitization:	0.079
Carcinogencity:	0.932
Eye Corrosion:	0.004
Eye Irritation:	0.974
Respiratory Toxicity:	0.141

Download Data

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

Natural Product: NPC1249

Natural Product ID:	NPC1249
*Common Name:**	1,8-Dimethoxy-3-Methyl-Anthraquinone
IUPAC Name:	1,8-dimethoxy-3-methylanthracene-9,10-dione
Synonyms:
Standard InCHIKey:	LODCICIWBUFMMY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O4/c1-9-7-11-15(13(8-9)21-3)17(19)14-10(16(11)18)5-4-6-12(14)20-2/h4-8H,1-3H3
SMILES:	COc1cc(C)cc2c1C(=O)c1c(C2=O)cccc1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL289530
PubChem CID:	189763
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4278	Wikstroemia monticola	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4278	Wikstroemia monticola	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25238	Rheum coreanum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1671.1	Xanthium strumarium var. canadense	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25238	Rheum coreanum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6675	Aplophyllum myrtifolium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4278	Wikstroemia monticola	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO559	Mimusops globosa	Species	Sapotaceae	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
Others	6

Activity Type	# Activity
Cell Line	2
Individual Protein	2
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	ID50	=	0.000028	M	PMID[479934]
NPT116	Cell Line	HL-60	Homo sapiens	ID50	=	1.0	M	PMID[479934]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Inhibition	=	59.2	%	PMID[479935]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	Inhibition	=	62.1	%	PMID[479935]
NPT317	Uncleic Acid	Nucleic Acid		ID50	=	0.000019	M	PMID[479934]
NPT317	Uncleic Acid	Nucleic Acid		Ratio	=	1.9	n.a.	PMID[479934]

☑ 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 NPC1249 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	438
0.1-0.2	1729
0.2-0.3	4005
0.3-0.4	10970
0.4-0.5	7413
0.5-0.6	4107
0.6-0.7	7805
0.7-0.8	5688
0.8-0.85	454
0.85-0.9	79
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9621	High Similarity	NPC1268
0.9606	High Similarity	NPC57552
0.9394	High Similarity	NPC141934
0.9333	High Similarity	NPC124365
0.9203	High Similarity	NPC49282
0.9197	High Similarity	NPC167663
0.9	High Similarity	NPC300540
0.8986	High Similarity	NPC69755
0.8984	High Similarity	NPC182646
0.8936	High Similarity	NPC190648
0.8936	High Similarity	NPC312929
0.8936	High Similarity	NPC56433
0.8936	High Similarity	NPC289042
0.8936	High Similarity	NPC126767
0.8936	High Similarity	NPC245584
0.8936	High Similarity	NPC118027
0.8921	High Similarity	NPC53016
0.8915	High Similarity	NPC56332
0.8905	High Similarity	NPC223336
0.8881	High Similarity	NPC290954
0.8881	High Similarity	NPC255641
0.8881	High Similarity	NPC470406
0.8873	High Similarity	NPC472056
0.8872	High Similarity	NPC301717
0.8855	High Similarity	NPC45537
0.8819	High Similarity	NPC302783
0.8819	High Similarity	NPC473201
0.8788	High Similarity	NPC282923
0.8779	High Similarity	NPC177925
0.8779	High Similarity	NPC474264
0.8777	High Similarity	NPC149780
0.875	High Similarity	NPC474660
0.875	High Similarity	NPC470568
0.875	High Similarity	NPC147735
0.875	High Similarity	NPC294646
0.8723	High Similarity	NPC19896
0.8699	High Similarity	NPC208806
0.869	High Similarity	NPC470569
0.8667	High Similarity	NPC183103
0.8667	High Similarity	NPC474340
0.8662	High Similarity	NPC478019
0.8661	High Similarity	NPC171023
0.8647	High Similarity	NPC125887
0.8639	High Similarity	NPC226656
0.8639	High Similarity	NPC66508
0.8633	High Similarity	NPC470407
0.8633	High Similarity	NPC26924
0.863	High Similarity	NPC154683
0.863	High Similarity	NPC40356
0.8623	High Similarity	NPC301341
0.8623	High Similarity	NPC284184
0.8621	High Similarity	NPC473466
0.8613	High Similarity	NPC22222
0.8613	High Similarity	NPC281513
0.8603	High Similarity	NPC115458
0.8593	High Similarity	NPC164295
0.8593	High Similarity	NPC205992
0.8593	High Similarity	NPC205360
0.8592	High Similarity	NPC21599
0.8592	High Similarity	NPC189650
0.8592	High Similarity	NPC193703
0.8582	High Similarity	NPC99731
0.8571	High Similarity	NPC107109
0.8571	High Similarity	NPC109007
0.8571	High Similarity	NPC428300
0.8571	High Similarity	NPC315578
0.8561	High Similarity	NPC103540
0.8552	High Similarity	NPC329933
0.8552	High Similarity	NPC70764
0.8551	High Similarity	NPC232996
0.8542	High Similarity	NPC478018
0.8542	High Similarity	NPC34802
0.8542	High Similarity	NPC71055
0.8529	High Similarity	NPC70622
0.8523	High Similarity	NPC178976
0.8521	High Similarity	NPC277369
0.8521	High Similarity	NPC215451
0.8507	High Similarity	NPC48248
0.8496	Intermediate Similarity	NPC474737
0.8489	Intermediate Similarity	NPC186647
0.8489	Intermediate Similarity	NPC290601
0.8485	Intermediate Similarity	NPC142956
0.8485	Intermediate Similarity	NPC173978
0.8478	Intermediate Similarity	NPC283088
0.8467	Intermediate Similarity	NPC324736
0.8462	Intermediate Similarity	NPC48762
0.8462	Intermediate Similarity	NPC274085
0.8462	Intermediate Similarity	NPC89664
0.8456	Intermediate Similarity	NPC477412
0.8456	Intermediate Similarity	NPC77807
0.8456	Intermediate Similarity	NPC14561
0.8456	Intermediate Similarity	NPC239134
0.8456	Intermediate Similarity	NPC5379
0.8451	Intermediate Similarity	NPC182255
0.8451	Intermediate Similarity	NPC94076
0.8451	Intermediate Similarity	NPC49108
0.845	Intermediate Similarity	NPC201284
0.8446	Intermediate Similarity	NPC214632
0.8444	Intermediate Similarity	NPC146647
0.8444	Intermediate Similarity	NPC34414
0.8435	Intermediate Similarity	NPC118427
0.8435	Intermediate Similarity	NPC39819
0.8433	Intermediate Similarity	NPC298884
0.8425	Intermediate Similarity	NPC80370
0.8421	Intermediate Similarity	NPC2771
0.8421	Intermediate Similarity	NPC232387
0.8417	Intermediate Similarity	NPC474813
0.8417	Intermediate Similarity	NPC272268
0.8414	Intermediate Similarity	NPC119767
0.8411	Intermediate Similarity	NPC284495
0.8409	Intermediate Similarity	NPC375356
0.8403	Intermediate Similarity	NPC73416
0.8403	Intermediate Similarity	NPC160777
0.8403	Intermediate Similarity	NPC34482
0.84	Intermediate Similarity	NPC199463
0.84	Intermediate Similarity	NPC37543
0.8394	Intermediate Similarity	NPC309430
0.8394	Intermediate Similarity	NPC58685
0.8392	Intermediate Similarity	NPC66593
0.8392	Intermediate Similarity	NPC476473
0.8392	Intermediate Similarity	NPC472840
0.8392	Intermediate Similarity	NPC84266
0.8382	Intermediate Similarity	NPC199253
0.8382	Intermediate Similarity	NPC136588
0.8382	Intermediate Similarity	NPC475741
0.838	Intermediate Similarity	NPC171094
0.8378	Intermediate Similarity	NPC164912
0.8378	Intermediate Similarity	NPC137125
0.8369	Intermediate Similarity	NPC477408
0.8367	Intermediate Similarity	NPC205766
0.8358	Intermediate Similarity	NPC3224
0.8357	Intermediate Similarity	NPC245923
0.8356	Intermediate Similarity	NPC472841
0.8356	Intermediate Similarity	NPC256672
0.8356	Intermediate Similarity	NPC27221
0.8356	Intermediate Similarity	NPC474107
0.8356	Intermediate Similarity	NPC172329
0.8356	Intermediate Similarity	NPC2569
0.8356	Intermediate Similarity	NPC7025
0.8356	Intermediate Similarity	NPC5537
0.8355	Intermediate Similarity	NPC311740
0.8345	Intermediate Similarity	NPC225173
0.8345	Intermediate Similarity	NPC163846
0.8345	Intermediate Similarity	NPC147250
0.8345	Intermediate Similarity	NPC473927
0.8345	Intermediate Similarity	NPC95485
0.8345	Intermediate Similarity	NPC89504
0.8345	Intermediate Similarity	NPC470570
0.8345	Intermediate Similarity	NPC88065
0.8333	Intermediate Similarity	NPC300274
0.8333	Intermediate Similarity	NPC477409
0.8333	Intermediate Similarity	NPC475201
0.8333	Intermediate Similarity	NPC229787
0.8333	Intermediate Similarity	NPC93241
0.8333	Intermediate Similarity	NPC182428
0.8333	Intermediate Similarity	NPC225051
0.8333	Intermediate Similarity	NPC27798
0.8322	Intermediate Similarity	NPC477691
0.8322	Intermediate Similarity	NPC474300
0.8322	Intermediate Similarity	NPC135522
0.8322	Intermediate Similarity	NPC329844
0.8311	Intermediate Similarity	NPC70320
0.8311	Intermediate Similarity	NPC478148
0.8311	Intermediate Similarity	NPC258249
0.8311	Intermediate Similarity	NPC144283
0.8311	Intermediate Similarity	NPC474414
0.8311	Intermediate Similarity	NPC230848
0.8311	Intermediate Similarity	NPC474417
0.8311	Intermediate Similarity	NPC149526
0.831	Intermediate Similarity	NPC472366
0.8301	Intermediate Similarity	NPC278329
0.8301	Intermediate Similarity	NPC146837
0.8299	Intermediate Similarity	NPC300983
0.8299	Intermediate Similarity	NPC97029
0.8299	Intermediate Similarity	NPC65775
0.8299	Intermediate Similarity	NPC65589
0.8299	Intermediate Similarity	NPC10027
0.8299	Intermediate Similarity	NPC97028
0.8299	Intermediate Similarity	NPC158338
0.8299	Intermediate Similarity	NPC100985
0.8299	Intermediate Similarity	NPC288036
0.8298	Intermediate Similarity	NPC61590
0.8298	Intermediate Similarity	NPC13715
0.8296	Intermediate Similarity	NPC470841
0.8289	Intermediate Similarity	NPC472060
0.8289	Intermediate Similarity	NPC472052
0.8289	Intermediate Similarity	NPC470342
0.8289	Intermediate Similarity	NPC84571
0.8289	Intermediate Similarity	NPC476506
0.8288	Intermediate Similarity	NPC123202
0.8288	Intermediate Similarity	NPC125801
0.8288	Intermediate Similarity	NPC7943
0.8288	Intermediate Similarity	NPC22005
0.8286	Intermediate Similarity	NPC77955
0.8278	Intermediate Similarity	NPC44199
0.8278	Intermediate Similarity	NPC263483
0.8276	Intermediate Similarity	NPC469764
0.8276	Intermediate Similarity	NPC28632
0.8273	Intermediate Similarity	NPC288089
0.8273	Intermediate Similarity	NPC223354

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 NPC1249 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	397
0.1-0.2	982
0.2-0.3	1328
0.3-0.4	2620
0.4-0.5	2031
0.5-0.6	1165
0.6-0.7	474
0.7-0.8	139
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8811	High Similarity	NPD3226	Approved
0.8696	High Similarity	NPD2346	Discontinued
0.8561	High Similarity	NPD1470	Approved
0.8258	Intermediate Similarity	NPD1201	Approved
0.8222	Intermediate Similarity	NPD2798	Approved
0.8168	Intermediate Similarity	NPD1651	Approved
0.8156	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD2313	Discontinued
0.8079	Intermediate Similarity	NPD7819	Suspended
0.8074	Intermediate Similarity	NPD1876	Approved
0.8065	Intermediate Similarity	NPD6232	Discontinued
0.8042	Intermediate Similarity	NPD1471	Phase 3
0.8028	Intermediate Similarity	NPD2799	Discontinued
0.8025	Intermediate Similarity	NPD7473	Discontinued
0.8014	Intermediate Similarity	NPD1607	Approved
0.7985	Intermediate Similarity	NPD1281	Approved
0.7972	Intermediate Similarity	NPD2935	Discontinued
0.7972	Intermediate Similarity	NPD2796	Approved
0.7926	Intermediate Similarity	NPD3972	Approved
0.7902	Intermediate Similarity	NPD1510	Phase 2
0.7902	Intermediate Similarity	NPD3748	Approved
0.7877	Intermediate Similarity	NPD7003	Approved
0.7872	Intermediate Similarity	NPD1240	Approved
0.781	Intermediate Similarity	NPD1283	Approved
0.7808	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6959	Discontinued
0.7724	Intermediate Similarity	NPD5406	Approved
0.7724	Intermediate Similarity	NPD5408	Approved
0.7724	Intermediate Similarity	NPD5404	Approved
0.7724	Intermediate Similarity	NPD5405	Approved
0.7714	Intermediate Similarity	NPD6832	Phase 2
0.7707	Intermediate Similarity	NPD5494	Approved
0.7697	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD2344	Approved
0.7669	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2534	Approved
0.7667	Intermediate Similarity	NPD2532	Approved
0.7667	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2533	Approved
0.7635	Intermediate Similarity	NPD3750	Approved
0.7635	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD5691	Approved
0.7622	Intermediate Similarity	NPD4307	Phase 2
0.7622	Intermediate Similarity	NPD2979	Phase 3
0.7619	Intermediate Similarity	NPD1549	Phase 2
0.7619	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD3764	Approved
0.7603	Intermediate Similarity	NPD1551	Phase 2
0.7597	Intermediate Similarity	NPD7411	Suspended
0.7576	Intermediate Similarity	NPD8313	Approved
0.7576	Intermediate Similarity	NPD8312	Approved
0.7574	Intermediate Similarity	NPD17	Approved
0.7574	Intermediate Similarity	NPD4626	Approved
0.7564	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6599	Discontinued
0.7532	Intermediate Similarity	NPD4380	Phase 2
0.7516	Intermediate Similarity	NPD7768	Phase 2
0.75	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7390	Discontinued
0.7471	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7458	Discontinued
0.7468	Intermediate Similarity	NPD3749	Approved
0.7467	Intermediate Similarity	NPD2309	Approved
0.7464	Intermediate Similarity	NPD1611	Approved
0.7456	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD920	Approved
0.745	Intermediate Similarity	NPD1243	Approved
0.7448	Intermediate Similarity	NPD1933	Approved
0.7445	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1934	Approved
0.7434	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7177	Discontinued
0.7423	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4308	Phase 3
0.741	Intermediate Similarity	NPD1608	Approved
0.74	Intermediate Similarity	NPD4628	Phase 3
0.7389	Intermediate Similarity	NPD2801	Approved
0.7386	Intermediate Similarity	NPD6273	Approved
0.7378	Intermediate Similarity	NPD5844	Phase 1
0.7376	Intermediate Similarity	NPD3267	Approved
0.7376	Intermediate Similarity	NPD3266	Approved
0.7376	Intermediate Similarity	NPD1203	Approved
0.7368	Intermediate Similarity	NPD6799	Approved
0.7368	Intermediate Similarity	NPD1511	Approved
0.7365	Intermediate Similarity	NPD2438	Suspended
0.7365	Intermediate Similarity	NPD2531	Phase 2
0.7361	Intermediate Similarity	NPD411	Approved
0.7358	Intermediate Similarity	NPD7075	Discontinued
0.7351	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD3926	Phase 2
0.7342	Intermediate Similarity	NPD5402	Approved
0.7338	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6801	Discontinued
0.732	Intermediate Similarity	NPD5401	Approved
0.732	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD1241	Discontinued
0.731	Intermediate Similarity	NPD8032	Phase 2
0.7303	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3882	Suspended
0.7293	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4625	Phase 3
0.7286	Intermediate Similarity	NPD9717	Approved
0.7285	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1512	Approved
0.7248	Intermediate Similarity	NPD6099	Approved
0.7248	Intermediate Similarity	NPD6100	Approved
0.7246	Intermediate Similarity	NPD6559	Discontinued
0.7233	Intermediate Similarity	NPD3817	Phase 2
0.7226	Intermediate Similarity	NPD5536	Phase 2
0.7226	Intermediate Similarity	NPD5403	Approved
0.7222	Intermediate Similarity	NPD1247	Approved
0.7219	Intermediate Similarity	NPD2800	Approved
0.7215	Intermediate Similarity	NPD6844	Discontinued
0.7211	Intermediate Similarity	NPD447	Suspended
0.7208	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD919	Approved
0.7203	Intermediate Similarity	NPD1019	Discontinued
0.7175	Intermediate Similarity	NPD6782	Approved
0.7175	Intermediate Similarity	NPD6777	Approved
0.7175	Intermediate Similarity	NPD6778	Approved
0.7175	Intermediate Similarity	NPD6776	Approved
0.7175	Intermediate Similarity	NPD6781	Approved
0.7175	Intermediate Similarity	NPD6779	Approved
0.7175	Intermediate Similarity	NPD6780	Approved
0.7153	Intermediate Similarity	NPD9493	Approved
0.7143	Intermediate Similarity	NPD943	Approved
0.7135	Intermediate Similarity	NPD8150	Discontinued
0.7133	Intermediate Similarity	NPD2797	Approved
0.7123	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3268	Approved
0.7122	Intermediate Similarity	NPD3025	Approved
0.7122	Intermediate Similarity	NPD3024	Approved
0.7119	Intermediate Similarity	NPD8285	Discontinued
0.7113	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6280	Approved
0.7107	Intermediate Similarity	NPD6279	Approved
0.7091	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6166	Phase 2
0.7073	Intermediate Similarity	NPD5711	Approved
0.7073	Intermediate Similarity	NPD5710	Approved
0.7056	Intermediate Similarity	NPD7435	Discontinued
0.7056	Intermediate Similarity	NPD7698	Approved
0.7056	Intermediate Similarity	NPD7697	Approved
0.7056	Intermediate Similarity	NPD7696	Phase 3
0.7055	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6651	Approved
0.7044	Intermediate Similarity	NPD5889	Approved
0.7044	Intermediate Similarity	NPD5890	Approved
0.7037	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2651	Approved
0.7025	Intermediate Similarity	NPD2649	Approved
0.7023	Intermediate Similarity	NPD164	Approved
0.7021	Intermediate Similarity	NPD3026	Approved
0.7021	Intermediate Similarity	NPD3023	Approved
0.702	Intermediate Similarity	NPD4477	Approved
0.702	Intermediate Similarity	NPD4476	Approved
0.7017	Intermediate Similarity	NPD7870	Phase 2
0.7017	Intermediate Similarity	NPD7871	Phase 2
0.7014	Intermediate Similarity	NPD1164	Approved
0.7007	Intermediate Similarity	NPD5951	Approved
0.7006	Intermediate Similarity	NPD3751	Discontinued
0.7006	Intermediate Similarity	NPD3818	Discontinued
0.7	Intermediate Similarity	NPD37	Approved
0.7	Intermediate Similarity	NPD6823	Phase 2
0.6993	Remote Similarity	NPD2654	Approved
0.6993	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4662	Approved
0.6987	Remote Similarity	NPD4661	Approved
0.6982	Remote Similarity	NPD5953	Discontinued
0.6981	Remote Similarity	NPD6585	Discontinued
0.6975	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3300	Phase 2
0.6954	Remote Similarity	NPD7033	Discontinued
0.695	Remote Similarity	NPD3019	Approved
0.695	Remote Similarity	NPD1778	Approved
0.694	Remote Similarity	NPD2182	Approved
0.6939	Remote Similarity	NPD7008	Discontinued
0.6934	Remote Similarity	NPD5283	Phase 1
0.6914	Remote Similarity	NPD2296	Approved
0.6914	Remote Similarity	NPD4288	Approved
0.6914	Remote Similarity	NPD5977	Approved
0.6914	Remote Similarity	NPD5978	Approved
0.6913	Remote Similarity	NPD4060	Phase 1
0.6902	Remote Similarity	NPD7701	Phase 2
0.6893	Remote Similarity	NPD6534	Approved
0.6893	Remote Similarity	NPD6535	Approved
0.6892	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6798	Discontinued

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