NPASS Compound

Structure

CID270913 OpenBabel06191716072D 25 27 0 0 1 0 0 0 0 0999 V2000 -4.2202 0.5070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0746 -0.2988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2257 -3.0580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 1.0124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8359 -1.4482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3436 0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5076 0.4819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5084 -2.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6716 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 -0.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6718 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5082 -1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6718 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3437 -0.9649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5078 0.4830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6720 -0.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8362 0.4824 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 2.9002 1.3634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5908 -2.7109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5375 -1.4660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2099 -1.4647 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5078 1.4830 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8363 1.4824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8359 -1.4479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 8 1 0 0 0 0 5 9 1 0 0 0 0 5 10 2 0 0 0 0 6 14 2 0 0 0 0 6 15 1 0 0 0 0 7 11 1 0 0 0 0 7 19 2 0 0 0 0 8 12 1 0 0 0 0 8 20 2 0 0 0 0 9 11 1 0 0 0 0 9 21 2 0 0 0 0 10 18 1 0 0 0 0 10 25 1 0 0 0 0 11 17 2 0 0 0 0 12 14 1 0 0 0 0 12 16 2 0 0 0 0 13 15 2 0 0 0 0 13 16 1 0 0 0 0 13 18 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 0 0 0 0 18 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.09
Volume:	334.655
LogP:	2.324
LogD:	0.752
LogS:	-2.886
# Rotatable Bonds:	2
TPSA:	117.97
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.616
Synthetic Accessibility Score:	4.248
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.883
MDCK Permeability:	2.1458870833157562e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	92.93888854980469%
Volume Distribution (VD):	0.428
Pgp-substrate:	4.099302768707275%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.795
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.832
CYP2C9-inhibitor:	0.069
CYP2C9-substrate:	0.895
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.31
CYP3A4-substrate:	0.85

ADMET: Excretion

Clearance (CL):	10.015
Half-life (T1/2):	0.4

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.397
Drug-inuced Liver Injury (DILI):	0.82
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.793
Maximum Recommended Daily Dose:	0.491
Skin Sensitization:	0.463
Carcinogencity:	0.687
Eye Corrosion:	0.038
Eye Irritation:	0.87
Respiratory Toxicity:	0.9

Download Data

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

Natural Product: NPC270913

Natural Product ID:	NPC270913
*Common Name:**	ICTZCAHDGHPRQR-GOSISDBHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ICTZCAHDGHPRQR-GOSISDBHSA-N
Standard InCHI:	InChI=1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,22-24H,1-4H3/t18-/m1/s1
SMILES:	Cc1c(c(C(=O)C)c2c(c1O)[C@@]1(C)C(=CC(=O)C(=C1O)C(=O)C)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1454474
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[22233034]
NPO3729	Cetraria islandica	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561895]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8083	Medicago falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25424	Putterlickia verrucosa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8083	Medicago falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6513	Vernonia condensata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3729	Cetraria islandica	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4633	Calypogeia integristipula	Species	Calypogeiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2777	Cirsium brevistylum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5786	Desmodium oxyphyllum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25424	Putterlickia verrucosa	Species	Celastraceae	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
Potency	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Potency	n.a.	15848.9	nM	PMID[456432]

☑ 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 NPC270913 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	375
0.1-0.2	1620
0.2-0.3	3969
0.3-0.4	9708
0.4-0.5	9530
0.5-0.6	4397
0.6-0.7	6485
0.7-0.8	4769
0.8-0.85	1419
0.85-0.9	387
0.9-0.95	33
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9925	High Similarity	NPC82920
0.9925	High Similarity	NPC164697
0.9925	High Similarity	NPC289660
0.9852	High Similarity	NPC111201
0.9203	High Similarity	NPC268178
0.9203	High Similarity	NPC180501
0.9203	High Similarity	NPC54820
0.9143	High Similarity	NPC316911
0.9143	High Similarity	NPC316560
0.9078	High Similarity	NPC325346
0.9078	High Similarity	NPC326193
0.9078	High Similarity	NPC96791
0.9078	High Similarity	NPC470636
0.9078	High Similarity	NPC226942
0.9078	High Similarity	NPC323884
0.9078	High Similarity	NPC321629
0.9078	High Similarity	NPC321148
0.9034	High Similarity	NPC321896
0.9034	High Similarity	NPC476185
0.9014	High Similarity	NPC11700
0.9007	High Similarity	NPC74397
0.8986	High Similarity	NPC101752
0.8951	High Similarity	NPC470674
0.8951	High Similarity	NPC71184
0.8951	High Similarity	NPC470673
0.8951	High Similarity	NPC206212
0.8951	High Similarity	NPC117716
0.8944	High Similarity	NPC472344
0.8936	High Similarity	NPC477272
0.8929	High Similarity	NPC470672
0.8929	High Similarity	NPC470671
0.8929	High Similarity	NPC474487
0.8929	High Similarity	NPC183639
0.8929	High Similarity	NPC477055
0.8929	High Similarity	NPC131130
0.8929	High Similarity	NPC474504
0.8929	High Similarity	NPC477056
0.8929	High Similarity	NPC199458
0.8921	High Similarity	NPC174999
0.8881	High Similarity	NPC262935
0.8881	High Similarity	NPC251182
0.8881	High Similarity	NPC172182
0.8865	High Similarity	NPC241975
0.8865	High Similarity	NPC19476
0.8857	High Similarity	NPC474624
0.8857	High Similarity	NPC138047
0.8857	High Similarity	NPC131782
0.8841	High Similarity	NPC108113
0.8841	High Similarity	NPC93756
0.8836	High Similarity	NPC471114
0.8828	High Similarity	NPC10990
0.8828	High Similarity	NPC300988
0.8811	High Similarity	NPC294432
0.8811	High Similarity	NPC112829
0.8811	High Similarity	NPC276565
0.8811	High Similarity	NPC470556
0.8803	High Similarity	NPC11056
0.8794	High Similarity	NPC254168
0.8794	High Similarity	NPC272844
0.8794	High Similarity	NPC470669
0.8794	High Similarity	NPC248995
0.8794	High Similarity	NPC470668
0.8794	High Similarity	NPC470083
0.8794	High Similarity	NPC219584
0.8786	High Similarity	NPC470983
0.8786	High Similarity	NPC470982
0.8786	High Similarity	NPC156910
0.8777	High Similarity	NPC125920
0.8776	High Similarity	NPC476509
0.8768	High Similarity	NPC215875
0.8768	High Similarity	NPC285054
0.8768	High Similarity	NPC15834
0.8768	High Similarity	NPC10971
0.8767	High Similarity	NPC135325
0.8767	High Similarity	NPC168085
0.8759	High Similarity	NPC82534
0.8759	High Similarity	NPC210826
0.875	High Similarity	NPC474939
0.875	High Similarity	NPC473812
0.875	High Similarity	NPC307895
0.875	High Similarity	NPC212932
0.875	High Similarity	NPC5990
0.875	High Similarity	NPC190637
0.875	High Similarity	NPC33653
0.875	High Similarity	NPC184738
0.875	High Similarity	NPC9117
0.875	High Similarity	NPC470909
0.875	High Similarity	NPC473813
0.875	High Similarity	NPC24821
0.875	High Similarity	NPC96216
0.875	High Similarity	NPC470553
0.875	High Similarity	NPC18886
0.875	High Similarity	NPC293053
0.8741	High Similarity	NPC171870
0.8732	High Similarity	NPC23257
0.8732	High Similarity	NPC240305
0.8732	High Similarity	NPC301217
0.8732	High Similarity	NPC217186
0.8732	High Similarity	NPC55018
0.8732	High Similarity	NPC472343
0.8732	High Similarity	NPC220062
0.8732	High Similarity	NPC96565
0.8732	High Similarity	NPC37206
0.8732	High Similarity	NPC137009
0.8732	High Similarity	NPC303633
0.8732	High Similarity	NPC139554
0.8732	High Similarity	NPC53181
0.8732	High Similarity	NPC216978
0.8723	High Similarity	NPC322301
0.8723	High Similarity	NPC255801
0.8716	High Similarity	NPC470675
0.8716	High Similarity	NPC476162
0.8716	High Similarity	NPC473131
0.8714	High Similarity	NPC60667
0.8707	High Similarity	NPC226644
0.8707	High Similarity	NPC37226
0.8707	High Similarity	NPC178202
0.8707	High Similarity	NPC317492
0.8705	High Similarity	NPC16197
0.8699	High Similarity	NPC308200
0.8699	High Similarity	NPC12148
0.8699	High Similarity	NPC202494
0.8699	High Similarity	NPC130581
0.8696	High Similarity	NPC27490
0.869	High Similarity	NPC216538
0.869	High Similarity	NPC472447
0.869	High Similarity	NPC224714
0.869	High Similarity	NPC297788
0.869	High Similarity	NPC472446
0.869	High Similarity	NPC271288
0.869	High Similarity	NPC273538
0.869	High Similarity	NPC288910
0.869	High Similarity	NPC470890
0.869	High Similarity	NPC326500
0.869	High Similarity	NPC133060
0.869	High Similarity	NPC118059
0.869	High Similarity	NPC470554
0.8686	High Similarity	NPC186628
0.8686	High Similarity	NPC84772
0.8684	High Similarity	NPC313368
0.8681	High Similarity	NPC200694
0.8681	High Similarity	NPC144499
0.8681	High Similarity	NPC473042
0.8681	High Similarity	NPC204469
0.8675	High Similarity	NPC196448
0.8671	High Similarity	NPC270883
0.8671	High Similarity	NPC471587
0.8671	High Similarity	NPC159275
0.8671	High Similarity	NPC469818
0.8671	High Similarity	NPC69769
0.8671	High Similarity	NPC241100
0.8671	High Similarity	NPC172986
0.8671	High Similarity	NPC221173
0.8671	High Similarity	NPC261227
0.8662	High Similarity	NPC201395
0.8658	High Similarity	NPC470353
0.8658	High Similarity	NPC5871
0.8649	High Similarity	NPC230713
0.8649	High Similarity	NPC321387
0.8649	High Similarity	NPC470908
0.8649	High Similarity	NPC327059
0.8649	High Similarity	NPC472421
0.8649	High Similarity	NPC78335
0.8643	High Similarity	NPC236974
0.8643	High Similarity	NPC103842
0.8643	High Similarity	NPC144027
0.8639	High Similarity	NPC145467
0.8639	High Similarity	NPC39195
0.8633	High Similarity	NPC470988
0.8633	High Similarity	NPC203817
0.863	High Similarity	NPC178343
0.863	High Similarity	NPC470676
0.863	High Similarity	NPC5820
0.863	High Similarity	NPC300267
0.863	High Similarity	NPC187282
0.863	High Similarity	NPC473135
0.863	High Similarity	NPC124729
0.863	High Similarity	NPC477955
0.863	High Similarity	NPC290133
0.863	High Similarity	NPC470910
0.863	High Similarity	NPC24136
0.863	High Similarity	NPC473132
0.863	High Similarity	NPC51641
0.863	High Similarity	NPC306488
0.863	High Similarity	NPC220418
0.863	High Similarity	NPC472629
0.8623	High Similarity	NPC324482
0.8623	High Similarity	NPC270369
0.8623	High Similarity	NPC250057
0.8623	High Similarity	NPC5515
0.8623	High Similarity	NPC279566
0.8621	High Similarity	NPC166138
0.8621	High Similarity	NPC106985
0.8621	High Similarity	NPC219915
0.8621	High Similarity	NPC18585
0.8621	High Similarity	NPC158874
0.8621	High Similarity	NPC225884
0.8613	High Similarity	NPC230818
0.8611	High Similarity	NPC476508
0.8611	High Similarity	NPC118840

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 NPC270913 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	1033
0.2-0.3	1882
0.3-0.4	2709
0.4-0.5	1866
0.5-0.6	932
0.6-0.7	268
0.7-0.8	102
0.8-0.85	15
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9851	High Similarity	NPD2800	Approved
0.8978	High Similarity	NPD6651	Approved
0.869	High Similarity	NPD4378	Clinical (unspecified phase)
0.8562	High Similarity	NPD2533	Approved
0.8562	High Similarity	NPD2532	Approved
0.8562	High Similarity	NPD2534	Approved
0.8435	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD1240	Approved
0.8151	Intermediate Similarity	NPD1549	Phase 2
0.8095	Intermediate Similarity	NPD1243	Approved
0.8069	Intermediate Similarity	NPD1510	Phase 2
0.8056	Intermediate Similarity	NPD1607	Approved
0.8039	Intermediate Similarity	NPD4380	Phase 2
0.8038	Intermediate Similarity	NPD6959	Discontinued
0.8027	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD2796	Approved
0.8	Intermediate Similarity	NPD1511	Approved
0.8	Intermediate Similarity	NPD7819	Suspended
0.7987	Intermediate Similarity	NPD7411	Suspended
0.7962	Intermediate Similarity	NPD7075	Discontinued
0.7961	Intermediate Similarity	NPD920	Approved
0.7959	Intermediate Similarity	NPD2344	Approved
0.7935	Intermediate Similarity	NPD1934	Approved
0.7922	Intermediate Similarity	NPD6599	Discontinued
0.7919	Intermediate Similarity	NPD3750	Approved
0.7898	Intermediate Similarity	NPD3882	Suspended
0.7895	Intermediate Similarity	NPD1512	Approved
0.7885	Intermediate Similarity	NPD2801	Approved
0.7885	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD5710	Approved
0.7875	Intermediate Similarity	NPD5711	Approved
0.7848	Intermediate Similarity	NPD3749	Approved
0.7821	Intermediate Similarity	NPD6801	Discontinued
0.78	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD7768	Phase 2
0.7778	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD6099	Approved
0.777	Intermediate Similarity	NPD6100	Approved
0.7763	Intermediate Similarity	NPD6799	Approved
0.775	Intermediate Similarity	NPD5494	Approved
0.7748	Intermediate Similarity	NPD2309	Approved
0.7736	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD2799	Discontinued
0.7697	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2935	Discontinued
0.7636	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD3748	Approved
0.7576	Intermediate Similarity	NPD3818	Discontinued
0.7561	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6166	Phase 2
0.7546	Intermediate Similarity	NPD6232	Discontinued
0.7534	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD2313	Discontinued
0.7533	Intermediate Similarity	NPD1551	Phase 2
0.753	Intermediate Similarity	NPD7286	Phase 2
0.7515	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD2654	Approved
0.7467	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD2403	Approved
0.7451	Intermediate Similarity	NPD4628	Phase 3
0.7451	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5953	Discontinued
0.7419	Intermediate Similarity	NPD7390	Discontinued
0.7405	Intermediate Similarity	NPD3226	Approved
0.7394	Intermediate Similarity	NPD3926	Phase 2
0.7381	Intermediate Similarity	NPD7074	Phase 3
0.7378	Intermediate Similarity	NPD1247	Approved
0.7368	Intermediate Similarity	NPD2346	Discontinued
0.7362	Intermediate Similarity	NPD919	Approved
0.7346	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD9717	Approved
0.7321	Intermediate Similarity	NPD7054	Approved
0.731	Intermediate Similarity	NPD1203	Approved
0.7305	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7472	Approved
0.7278	Intermediate Similarity	NPD1729	Discontinued
0.7273	Intermediate Similarity	NPD422	Phase 1
0.7267	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5124	Phase 1
0.7235	Intermediate Similarity	NPD6797	Phase 2
0.7222	Intermediate Similarity	NPD3972	Approved
0.7222	Intermediate Similarity	NPD1465	Phase 2
0.7219	Intermediate Similarity	NPD5844	Phase 1
0.72	Intermediate Similarity	NPD943	Approved
0.7193	Intermediate Similarity	NPD7251	Discontinued
0.7191	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4361	Phase 2
0.7181	Intermediate Similarity	NPD3268	Approved
0.7181	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2296	Approved
0.7172	Intermediate Similarity	NPD4749	Approved
0.717	Intermediate Similarity	NPD5403	Approved
0.7162	Intermediate Similarity	NPD4908	Phase 1
0.7152	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7808	Phase 3
0.7143	Intermediate Similarity	NPD6005	Phase 3
0.7143	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD2798	Approved
0.7143	Intermediate Similarity	NPD6002	Phase 3
0.7143	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4360	Phase 2
0.7135	Intermediate Similarity	NPD4363	Phase 3
0.7123	Intermediate Similarity	NPD6696	Suspended
0.7093	Intermediate Similarity	NPD6104	Discontinued
0.7075	Intermediate Similarity	NPD2797	Approved
0.7073	Intermediate Similarity	NPD5402	Approved
0.7052	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6832	Phase 2
0.7044	Intermediate Similarity	NPD5401	Approved
0.7044	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD447	Suspended
0.7039	Intermediate Similarity	NPD230	Phase 1
0.7034	Intermediate Similarity	NPD1610	Phase 2
0.7024	Intermediate Similarity	NPD7229	Phase 3
0.7013	Intermediate Similarity	NPD7033	Discontinued
0.7013	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5760	Phase 2
0.7012	Intermediate Similarity	NPD5761	Phase 2
0.7006	Intermediate Similarity	NPD4287	Approved
0.7	Intermediate Similarity	NPD4625	Phase 3
0.6994	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD8434	Phase 2
0.6986	Remote Similarity	NPD1608	Approved
0.6975	Remote Similarity	NPD7458	Discontinued
0.697	Remote Similarity	NPD4288	Approved
0.6959	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3764	Approved
0.6954	Remote Similarity	NPD411	Approved
0.6954	Remote Similarity	NPD1296	Phase 2
0.6936	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4308	Phase 3
0.6899	Remote Similarity	NPD7003	Approved
0.689	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2424	Discontinued
0.6879	Remote Similarity	NPD1241	Discontinued
0.6875	Remote Similarity	NPD1548	Phase 1
0.6875	Remote Similarity	NPD9545	Approved
0.6867	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5408	Approved
0.6859	Remote Similarity	NPD5405	Approved
0.6859	Remote Similarity	NPD5406	Approved
0.6859	Remote Similarity	NPD5404	Approved
0.6853	Remote Similarity	NPD9493	Approved
0.6848	Remote Similarity	NPD6280	Approved
0.6848	Remote Similarity	NPD6279	Approved
0.6846	Remote Similarity	NPD3266	Approved
0.6846	Remote Similarity	NPD1164	Approved
0.6846	Remote Similarity	NPD3267	Approved
0.6821	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1201	Approved
0.68	Remote Similarity	NPD1019	Discontinued
0.6781	Remote Similarity	NPD17	Approved
0.6779	Remote Similarity	NPD3225	Approved
0.6779	Remote Similarity	NPD1876	Approved
0.6779	Remote Similarity	NPD8651	Approved
0.6776	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7199	Phase 2
0.6757	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD37	Approved
0.6746	Remote Similarity	NPD6234	Discontinued
0.674	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD1470	Approved
0.6726	Remote Similarity	NPD4966	Approved
0.6726	Remote Similarity	NPD4965	Approved
0.6726	Remote Similarity	NPD4967	Phase 2
0.6725	Remote Similarity	NPD6808	Phase 2
0.671	Remote Similarity	NPD6355	Discontinued
0.6705	Remote Similarity	NPD3446	Phase 1
0.6687	Remote Similarity	NPD6273	Approved
0.6687	Remote Similarity	NPD5049	Phase 3
0.6686	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3751	Discontinued
0.6667	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1778	Approved
0.6646	Remote Similarity	NPD4476	Approved
0.6646	Remote Similarity	NPD4477	Approved
0.6645	Remote Similarity	NPD4307	Phase 2
0.6645	Remote Similarity	NPD2861	Phase 2
0.6645	Remote Similarity	NPD1612	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