NPASS Compound

Structure

NPC173137 OpenBabel07101718242D 24 27 0 0 1 0 0 0 0 0999 V2000 -4.3301 2.5000 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 0.8660 -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 -3.4641 -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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 2.5981 -0.5000 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 -4.3301 1.5000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 8 2 0 0 0 0 5 11 1 0 0 0 0 6 8 1 0 0 0 0 6 12 2 0 0 0 0 7 13 1 0 0 0 0 7 23 1 0 0 0 0 8 22 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 15 1 0 0 0 0 10 18 1 0 0 0 0 11 14 2 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 17 1 6 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 20 2 0 0 0 0 17 21 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.07
Volume:	311.439
LogP:	2.616
LogD:	2.404
LogS:	-3.707
# Rotatable Bonds:	1
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.724
Synthetic Accessibility Score:	3.642
Fsp3:	0.235
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:	-5.275
MDCK Permeability:	8.35281844047131e-06
Pgp-inhibitor:	0.009
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	95.74878692626953%
Volume Distribution (VD):	0.819
Pgp-substrate:	5.832773208618164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.668
CYP2C19-inhibitor:	0.762
CYP2C19-substrate:	0.28
CYP2C9-inhibitor:	0.689
CYP2C9-substrate:	0.664
CYP2D6-inhibitor:	0.642
CYP2D6-substrate:	0.379
CYP3A4-inhibitor:	0.77
CYP3A4-substrate:	0.334

ADMET: Excretion

Clearance (CL):	8.538
Half-life (T1/2):	0.415

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.195
Drug-inuced Liver Injury (DILI):	0.66
AMES Toxicity:	0.363
Rat Oral Acute Toxicity:	0.224
Maximum Recommended Daily Dose:	0.483
Skin Sensitization:	0.91
Carcinogencity:	0.546
Eye Corrosion:	0.003
Eye Irritation:	0.75
Respiratory Toxicity:	0.043

Download Data

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

Natural Product: NPC173137

Natural Product ID:	NPC173137
*Common Name:**	10-Demethylboeravinone C
IUPAC Name:	(6aR,12aS)-4,11,12a-trihydroxy-9-methoxy-6,6a-dihydrochromeno[3,4-b]chromen-12-one
Synonyms:	10-Demethylboeravinone C
Standard InCHIKey:	ZXZFBFOIMQWFPM-DYVFJYSZSA-N
Standard InCHI:	InChI=1S/C17H14O7/c1-22-8-5-11(19)14-12(6-8)24-13-7-23-15-9(3-2-4-10(15)18)17(13,21)16(14)20/h2-6,13,18-19,21H,7H2,1H3/t13-,17+/m1/s1
SMILES:	COc1cc(c2c(c1)O[C@@H]1COc3c(cccc3O)[C@]1(C2=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522566
PubChem CID:	44583826
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001607] Rotenoids [CHEMONTID:0003528] Rotenones

*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
NPO33416	boerhaavia diffusa	Species	n.a.	n.a.	roots	n.a.	n.a.	PMID[16792408]
NPO33416	boerhaavia diffusa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[23914900]

☑ 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	3

Activity Type	# Activity
Individual Protein	2
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	Inhibition	=	41.3	%	PMID[565107]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Inhibition	=	47.2	%	PMID[565107]
NPT548	Tissue	Ileum	Cavia porcellus	Emax	=	19.4	%	PMID[565106]

☑ 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 NPC173137 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	414
0.1-0.2	1721
0.2-0.3	4291
0.3-0.4	10299
0.4-0.5	7587
0.5-0.6	3563
0.6-0.7	4784
0.7-0.8	5401
0.8-0.85	2765
0.85-0.9	1525
0.9-0.95	324
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
0.9806	High Similarity	NPC224280
0.9806	High Similarity	NPC62261
0.9739	High Similarity	NPC55738
0.9679	High Similarity	NPC234052
0.9618	High Similarity	NPC477517
0.9608	High Similarity	NPC320825
0.9608	High Similarity	NPC13858
0.9608	High Similarity	NPC474638
0.9608	High Similarity	NPC326037
0.9548	High Similarity	NPC263449
0.9548	High Similarity	NPC470183
0.9545	High Similarity	NPC52530
0.9545	High Similarity	NPC471515
0.9545	High Similarity	NPC471479
0.9545	High Similarity	NPC67876
0.9539	High Similarity	NPC219582
0.9539	High Similarity	NPC302950
0.9539	High Similarity	NPC236637
0.9494	High Similarity	NPC471213
0.949	High Similarity	NPC472625
0.9487	High Similarity	NPC134783
0.9487	High Similarity	NPC471210
0.9487	High Similarity	NPC308992
0.9487	High Similarity	NPC472632
0.9484	High Similarity	NPC152904
0.9481	High Similarity	NPC255106
0.9481	High Similarity	NPC471500
0.9481	High Similarity	NPC235165
0.9481	High Similarity	NPC250922
0.9477	High Similarity	NPC203080
0.9477	High Similarity	NPC141212
0.9477	High Similarity	NPC18727
0.943	High Similarity	NPC36916
0.943	High Similarity	NPC58223
0.943	High Similarity	NPC36
0.943	High Similarity	NPC293319
0.943	High Similarity	NPC72787
0.943	High Similarity	NPC7154
0.943	High Similarity	NPC7688
0.943	High Similarity	NPC125039
0.9427	High Similarity	NPC474033
0.9427	High Similarity	NPC474034
0.9427	High Similarity	NPC474162
0.9427	High Similarity	NPC474150
0.9423	High Similarity	NPC119209
0.9423	High Similarity	NPC287328
0.9423	High Similarity	NPC118256
0.9423	High Similarity	NPC174953
0.9423	High Similarity	NPC282009
0.9423	High Similarity	NPC192686
0.9419	High Similarity	NPC474836
0.9419	High Similarity	NPC129684
0.9419	High Similarity	NPC156057
0.9419	High Similarity	NPC48208
0.9419	High Similarity	NPC99597
0.9419	High Similarity	NPC471209
0.9419	High Similarity	NPC299520
0.9419	High Similarity	NPC162869
0.9419	High Similarity	NPC27337
0.9419	High Similarity	NPC474208
0.9419	High Similarity	NPC475267
0.9419	High Similarity	NPC210084
0.9412	High Similarity	NPC61506
0.9412	High Similarity	NPC260491
0.9412	High Similarity	NPC240476
0.9412	High Similarity	NPC9743
0.9412	High Similarity	NPC260979
0.9412	High Similarity	NPC36835
0.9412	High Similarity	NPC246162
0.9383	High Similarity	NPC108202
0.9375	High Similarity	NPC152477
0.9375	High Similarity	NPC177480
0.9367	High Similarity	NPC186686
0.9367	High Similarity	NPC41301
0.9363	High Similarity	NPC471211
0.9363	High Similarity	NPC474038
0.9363	High Similarity	NPC471212
0.9363	High Similarity	NPC471499
0.9359	High Similarity	NPC473990
0.9359	High Similarity	NPC22192
0.9355	High Similarity	NPC278778
0.9355	High Similarity	NPC24640
0.9355	High Similarity	NPC291878
0.9355	High Similarity	NPC195796
0.9355	High Similarity	NPC303255
0.9355	High Similarity	NPC201837
0.9355	High Similarity	NPC35038
0.9351	High Similarity	NPC27532
0.9351	High Similarity	NPC469550
0.9351	High Similarity	NPC325028
0.9351	High Similarity	NPC246328
0.9351	High Similarity	NPC256346
0.9346	High Similarity	NPC54394
0.9346	High Similarity	NPC252933
0.9346	High Similarity	NPC200740
0.9346	High Similarity	NPC31363
0.9346	High Similarity	NPC125062
0.9342	High Similarity	NPC277032
0.9313	High Similarity	NPC8965
0.9313	High Similarity	NPC477154
0.9313	High Similarity	NPC6588
0.9313	High Similarity	NPC117854
0.9304	High Similarity	NPC472964
0.9299	High Similarity	NPC472624
0.9299	High Similarity	NPC139036
0.9299	High Similarity	NPC472902
0.9299	High Similarity	NPC200746
0.9299	High Similarity	NPC475784
0.9299	High Similarity	NPC474960
0.9299	High Similarity	NPC471744
0.9299	High Similarity	NPC36217
0.9299	High Similarity	NPC470326
0.9295	High Similarity	NPC469584
0.9295	High Similarity	NPC291508
0.9295	High Similarity	NPC472910
0.9295	High Similarity	NPC472911
0.9295	High Similarity	NPC245758
0.9295	High Similarity	NPC474055
0.9295	High Similarity	NPC96167
0.9295	High Similarity	NPC284820
0.9295	High Similarity	NPC473272
0.9295	High Similarity	NPC472913
0.9295	High Similarity	NPC472598
0.9295	High Similarity	NPC472914
0.9295	High Similarity	NPC222814
0.929	High Similarity	NPC255807
0.929	High Similarity	NPC477503
0.929	High Similarity	NPC44079
0.929	High Similarity	NPC26227
0.929	High Similarity	NPC200761
0.929	High Similarity	NPC67396
0.929	High Similarity	NPC470327
0.929	High Similarity	NPC37392
0.929	High Similarity	NPC45849
0.929	High Similarity	NPC2928
0.929	High Similarity	NPC201451
0.929	High Similarity	NPC31018
0.9286	High Similarity	NPC55205
0.9286	High Similarity	NPC19721
0.9286	High Similarity	NPC279989
0.9286	High Similarity	NPC257648
0.9286	High Similarity	NPC199100
0.9286	High Similarity	NPC120537
0.9286	High Similarity	NPC180234
0.9286	High Similarity	NPC82325
0.9286	High Similarity	NPC472912
0.9286	High Similarity	NPC477231
0.9281	High Similarity	NPC267117
0.9281	High Similarity	NPC338131
0.9281	High Similarity	NPC29231
0.9276	High Similarity	NPC188679
0.9276	High Similarity	NPC294852
0.9276	High Similarity	NPC321011
0.9259	High Similarity	NPC121333
0.9255	High Similarity	NPC165456
0.9255	High Similarity	NPC242395
0.9255	High Similarity	NPC326877
0.9255	High Similarity	NPC288813
0.925	High Similarity	NPC43319
0.925	High Similarity	NPC120593
0.9245	High Similarity	NPC248638
0.9245	High Similarity	NPC152659
0.9245	High Similarity	NPC124038
0.9245	High Similarity	NPC236521
0.9245	High Similarity	NPC475985
0.9241	High Similarity	NPC112418
0.9241	High Similarity	NPC289771
0.9241	High Similarity	NPC472634
0.9241	High Similarity	NPC26326
0.9241	High Similarity	NPC158188
0.9236	High Similarity	NPC250214
0.9236	High Similarity	NPC95936
0.9236	High Similarity	NPC476242
0.9236	High Similarity	NPC280680
0.9236	High Similarity	NPC204879
0.9231	High Similarity	NPC472916
0.9231	High Similarity	NPC245546
0.9231	High Similarity	NPC5322
0.9231	High Similarity	NPC470328
0.9231	High Similarity	NPC43243
0.9231	High Similarity	NPC247017
0.9231	High Similarity	NPC266960
0.9231	High Similarity	NPC265511
0.9231	High Similarity	NPC49824
0.9231	High Similarity	NPC472626
0.9231	High Similarity	NPC133970
0.9231	High Similarity	NPC6633
0.9231	High Similarity	NPC209614
0.9231	High Similarity	NPC470600
0.9231	High Similarity	NPC98661
0.9226	High Similarity	NPC292214
0.9226	High Similarity	NPC74924
0.9226	High Similarity	NPC206238
0.9226	High Similarity	NPC271779
0.9226	High Similarity	NPC167091
0.9226	High Similarity	NPC213896
0.9226	High Similarity	NPC179126
0.9226	High Similarity	NPC236223
0.9226	High Similarity	NPC78326
0.9226	High Similarity	NPC270620

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 NPC173137 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	940
0.2-0.3	1809
0.3-0.4	2622
0.4-0.5	1789
0.5-0.6	969
0.6-0.7	447
0.7-0.8	142
0.8-0.85	32
0.85-0.9	13
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9539	High Similarity	NPD1934	Approved
0.943	High Similarity	NPD6167	Clinical (unspecified phase)
0.943	High Similarity	NPD6168	Clinical (unspecified phase)
0.943	High Similarity	NPD6166	Phase 2
0.9226	High Similarity	NPD2393	Clinical (unspecified phase)
0.9108	High Similarity	NPD3882	Suspended
0.9103	High Similarity	NPD2801	Approved
0.902	High Similarity	NPD1512	Approved
0.8963	High Similarity	NPD7074	Phase 3
0.8909	High Similarity	NPD6797	Phase 2
0.8902	High Similarity	NPD7054	Approved
0.8889	High Similarity	NPD1511	Approved
0.8855	High Similarity	NPD7251	Discontinued
0.8848	High Similarity	NPD7472	Approved
0.882	High Similarity	NPD5494	Approved
0.8805	High Similarity	NPD3817	Phase 2
0.8802	High Similarity	NPD4338	Clinical (unspecified phase)
0.8802	High Similarity	NPD7808	Phase 3
0.875	High Similarity	NPD4868	Clinical (unspecified phase)
0.8727	High Similarity	NPD3818	Discontinued
0.8618	High Similarity	NPD1552	Clinical (unspecified phase)
0.8618	High Similarity	NPD1550	Clinical (unspecified phase)
0.859	High Similarity	NPD4378	Clinical (unspecified phase)
0.858	High Similarity	NPD7075	Discontinued
0.8571	High Similarity	NPD7993	Clinical (unspecified phase)
0.8562	High Similarity	NPD1549	Phase 2
0.8553	High Similarity	NPD4380	Phase 2
0.8509	High Similarity	NPD1465	Phase 2
0.8509	High Similarity	NPD7096	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6959	Discontinued
0.8291	Intermediate Similarity	NPD6799	Approved
0.8263	Intermediate Similarity	NPD6232	Discontinued
0.8247	Intermediate Similarity	NPD1510	Phase 2
0.8235	Intermediate Similarity	NPD5844	Phase 1
0.8232	Intermediate Similarity	NPD5402	Approved
0.8225	Intermediate Similarity	NPD7473	Discontinued
0.8221	Intermediate Similarity	NPD6801	Discontinued
0.821	Intermediate Similarity	NPD6599	Discontinued
0.8194	Intermediate Similarity	NPD2796	Approved
0.8171	Intermediate Similarity	NPD7819	Suspended
0.8125	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD3926	Phase 2
0.8105	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1240	Approved
0.8105	Intermediate Similarity	NPD943	Approved
0.8105	Intermediate Similarity	NPD1613	Approved
0.8095	Intermediate Similarity	NPD1247	Approved
0.807	Intermediate Similarity	NPD3751	Discontinued
0.8049	Intermediate Similarity	NPD7411	Suspended
0.8025	Intermediate Similarity	NPD5403	Approved
0.8024	Intermediate Similarity	NPD3749	Approved
0.8012	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD1607	Approved
0.7976	Intermediate Similarity	NPD919	Approved
0.7961	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD3787	Discontinued
0.791	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD6559	Discontinued
0.7875	Intermediate Similarity	NPD3750	Approved
0.7862	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD230	Phase 1
0.7812	Intermediate Similarity	NPD2800	Approved
0.7792	Intermediate Similarity	NPD3027	Phase 3
0.779	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7768	Phase 2
0.7716	Intermediate Similarity	NPD6190	Approved
0.7707	Intermediate Similarity	NPD447	Suspended
0.7688	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD2534	Approved
0.7683	Intermediate Similarity	NPD2532	Approved
0.7683	Intermediate Similarity	NPD2533	Approved
0.768	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6234	Discontinued
0.7657	Intermediate Similarity	NPD7228	Approved
0.7654	Intermediate Similarity	NPD4628	Phase 3
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.7625	Intermediate Similarity	NPD6099	Approved
0.7625	Intermediate Similarity	NPD6100	Approved
0.7594	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7685	Pre-registration
0.7578	Intermediate Similarity	NPD2344	Approved
0.7572	Intermediate Similarity	NPD7199	Phase 2
0.7562	Intermediate Similarity	NPD3748	Approved
0.7548	Intermediate Similarity	NPD9494	Approved
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6777	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD8313	Approved
0.75	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD4908	Phase 1
0.7485	Intermediate Similarity	NPD920	Approved
0.7485	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1933	Approved
0.7473	Intermediate Similarity	NPD8434	Phase 2
0.7473	Intermediate Similarity	NPD8150	Discontinued
0.7471	Intermediate Similarity	NPD37	Approved
0.7469	Intermediate Similarity	NPD2346	Discontinued
0.7453	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4967	Phase 2
0.7442	Intermediate Similarity	NPD4965	Approved
0.7442	Intermediate Similarity	NPD4966	Approved
0.744	Intermediate Similarity	NPD1653	Approved
0.7439	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2309	Approved
0.7386	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1610	Phase 2
0.7382	Intermediate Similarity	NPD7698	Approved
0.7382	Intermediate Similarity	NPD7697	Approved
0.7382	Intermediate Similarity	NPD7435	Discontinued
0.7382	Intermediate Similarity	NPD7696	Phase 3
0.7365	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2799	Discontinued
0.7345	Intermediate Similarity	NPD2403	Approved
0.734	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5953	Discontinued
0.7326	Intermediate Similarity	NPD4363	Phase 3
0.7326	Intermediate Similarity	NPD4360	Phase 2
0.732	Intermediate Similarity	NPD7701	Phase 2
0.7318	Intermediate Similarity	NPD7286	Phase 2
0.7305	Intermediate Similarity	NPD7390	Discontinued
0.7296	Intermediate Similarity	NPD6798	Discontinued
0.7296	Intermediate Similarity	NPD2313	Discontinued
0.729	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5242	Approved
0.7282	Intermediate Similarity	NPD8151	Discontinued
0.7277	Intermediate Similarity	NPD2493	Approved
0.7277	Intermediate Similarity	NPD2494	Approved
0.7273	Intermediate Similarity	NPD1243	Approved
0.7267	Intermediate Similarity	NPD6355	Discontinued
0.7262	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7870	Phase 2
0.7254	Intermediate Similarity	NPD7871	Phase 2
0.7246	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7033	Discontinued
0.7234	Intermediate Similarity	NPD6535	Approved
0.7234	Intermediate Similarity	NPD6534	Approved
0.7232	Intermediate Similarity	NPD5710	Approved
0.7232	Intermediate Similarity	NPD5711	Approved
0.7222	Intermediate Similarity	NPD6651	Approved
0.7211	Intermediate Similarity	NPD7699	Phase 2
0.7211	Intermediate Similarity	NPD7700	Phase 2
0.7208	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7783	Phase 2
0.7198	Intermediate Similarity	NPD7240	Approved
0.7197	Intermediate Similarity	NPD1203	Approved
0.7188	Intermediate Similarity	NPD3452	Approved
0.7188	Intermediate Similarity	NPD3450	Approved
0.7184	Intermediate Similarity	NPD5353	Approved
0.7179	Intermediate Similarity	NPD7584	Approved
0.7168	Intermediate Similarity	NPD6844	Discontinued
0.7165	Intermediate Similarity	NPD4583	Approved
0.7165	Intermediate Similarity	NPD4582	Approved
0.716	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7874	Approved
0.7152	Intermediate Similarity	NPD7266	Discontinued
0.7143	Intermediate Similarity	NPD7907	Approved
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7129	Intermediate Similarity	NPD4111	Phase 1
0.7129	Intermediate Similarity	NPD4665	Approved
0.7126	Intermediate Similarity	NPD8455	Phase 2
0.7125	Intermediate Similarity	NPD4625	Phase 3
0.7124	Intermediate Similarity	NPD1548	Phase 1
0.7121	Intermediate Similarity	NPD7801	Approved
0.7115	Intermediate Similarity	NPD9269	Phase 2
0.7115	Intermediate Similarity	NPD1608	Approved
0.7113	Intermediate Similarity	NPD4004	Approved
0.7113	Intermediate Similarity	NPD4002	Approved
0.7112	Intermediate Similarity	NPD4287	Approved
0.711	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2424	Discontinued
0.7107	Intermediate Similarity	NPD2861	Phase 2
0.7099	Intermediate Similarity	NPD4060	Phase 1
0.7093	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2354	Approved
0.7081	Intermediate Similarity	NPD3268	Approved
0.7077	Intermediate Similarity	NPD8320	Phase 1
0.7077	Intermediate Similarity	NPD8319	Approved
0.707	Intermediate Similarity	NPD4749	Approved
0.7068	Intermediate Similarity	NPD2974	Approved
0.7068	Intermediate Similarity	NPD2975	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