NPASS Compound

Structure

NPC93552 OpenBabel07101719522D 31 33 0 0 0 0 0 0 0 0999 V2000 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 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 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 -1.7321 -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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 5.1962 -3.0000 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 -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 4.3301 -1.5000 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 3.4641 -2.0000 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 -1.5000 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 6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 7 1 0 0 0 0 5 13 2 0 0 0 0 6 8 1 0 0 0 0 6 14 2 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 15 2 0 0 0 0 9 18 1 0 0 0 0 10 16 2 0 0 0 0 10 20 1 0 0 0 0 11 16 1 0 0 0 0 11 21 2 0 0 0 0 12 19 2 0 0 0 0 12 31 1 0 0 0 0 15 23 1 0 0 0 0 16 26 1 0 0 0 0 17 18 2 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 19 24 1 0 0 0 0 20 22 2 0 0 0 0 20 27 1 0 0 0 0 21 22 1 0 0 0 0 21 31 1 0 0 0 0 22 24 1 0 0 0 0 23 25 2 0 0 0 0 23 28 1 0 0 0 0 24 29 2 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.17
Volume:	441.663
LogP:	5.999
LogD:	3.032
LogS:	-2.975
# Rotatable Bonds:	5
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.328
Synthetic Accessibility Score:	3.223
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.973
MDCK Permeability:	9.546707588015124e-06
Pgp-inhibitor:	0.485
Pgp-substrate:	0.93
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	92.23246002197266%
Volume Distribution (VD):	0.911
Pgp-substrate:	8.866416931152344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.776
CYP1A2-substrate:	0.176
CYP2C19-inhibitor:	0.859
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.85
CYP2C9-substrate:	0.791
CYP2D6-inhibitor:	0.857
CYP2D6-substrate:	0.236
CYP3A4-inhibitor:	0.232
CYP3A4-substrate:	0.061

ADMET: Excretion

Clearance (CL):	8.686
Half-life (T1/2):	0.761

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.76
Drug-inuced Liver Injury (DILI):	0.412
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.32
Maximum Recommended Daily Dose:	0.437
Skin Sensitization:	0.949
Carcinogencity:	0.061
Eye Corrosion:	0.003
Eye Irritation:	0.783
Respiratory Toxicity:	0.117

Download Data

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

Natural Product: NPC93552

Natural Product ID:	NPC93552
*Common Name:**	5,7,3',4'-Tetrahydroxy-2',5'-Di(3-Methylbut-2-Enyl)Isoflavone
IUPAC Name:	3-[3,4-dihydroxy-2,5-bis(3-methylbut-2-enyl)phenyl]-5,7-dihydroxychromen-4-one
Synonyms:
Standard InCHIKey:	RWGZXUWGOARVDQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H26O6/c1-13(2)5-7-15-9-18(17(8-6-14(3)4)25(30)23(15)28)19-12-31-21-11-16(26)10-20(27)22(21)24(19)29/h5-6,9-12,26-28,30H,7-8H2,1-4H3
SMILES:	CC(=CCc1cc(c(CC=C(C)C)c(c1O)O)c1coc2cc(cc(c2c1=O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2442950
PubChem CID:	12096316
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002901] Isoflav-2-enes [CHEMONTID:0000494] Isoflavones [CHEMONTID:0003580] 2'-prenylated isoflavones

*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
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24054487]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24412339]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4010	Flemingia philippinensis	Species	Fabaceae	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	1
Ki	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT344	Individual Protein	Sialidase	Clostridium perfringens	Ki	=	7860.0	nM	PMID[523818]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	IC50	=	7850.0	nM	PMID[523818]

☑ 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 NPC93552 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	429
0.1-0.2	1800
0.2-0.3	4182
0.3-0.4	10708
0.4-0.5	7609
0.5-0.6	3484
0.6-0.7	5163
0.7-0.8	5209
0.8-0.85	2621
0.85-0.9	1223
0.9-0.95	251
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.966	High Similarity	NPC85131
0.9658	High Similarity	NPC203077
0.9658	High Similarity	NPC238279
0.9658	High Similarity	NPC166036
0.9597	High Similarity	NPC107109
0.9592	High Similarity	NPC38545
0.9592	High Similarity	NPC171916
0.9536	High Similarity	NPC37543
0.9536	High Similarity	NPC199463
0.9474	High Similarity	NPC85121
0.947	High Similarity	NPC14561
0.947	High Similarity	NPC77807
0.947	High Similarity	NPC5379
0.9463	High Similarity	NPC256406
0.9419	High Similarity	NPC303174
0.9408	High Similarity	NPC178976
0.94	High Similarity	NPC324233
0.94	High Similarity	NPC323626
0.9286	High Similarity	NPC84571
0.9276	High Similarity	NPC134287
0.9276	High Similarity	NPC130589
0.9272	High Similarity	NPC474993
0.9267	High Similarity	NPC470568
0.9262	High Similarity	NPC203747
0.9262	High Similarity	NPC80710
0.9262	High Similarity	NPC139364
0.9262	High Similarity	NPC254702
0.9262	High Similarity	NPC194653
0.9252	High Similarity	NPC38065
0.9252	High Similarity	NPC242893
0.9236	High Similarity	NPC43319
0.9231	High Similarity	NPC270837
0.9226	High Similarity	NPC311740
0.9221	High Similarity	NPC210459
0.9216	High Similarity	NPC282307
0.9216	High Similarity	NPC170026
0.9216	High Similarity	NPC475799
0.9216	High Similarity	NPC13779
0.9205	High Similarity	NPC470569
0.9205	High Similarity	NPC154345
0.92	High Similarity	NPC40290
0.92	High Similarity	NPC288036
0.92	High Similarity	NPC97029
0.92	High Similarity	NPC97028
0.92	High Similarity	NPC65589
0.92	High Similarity	NPC69430
0.92	High Similarity	NPC264289
0.92	High Similarity	NPC158338
0.92	High Similarity	NPC200060
0.92	High Similarity	NPC333691
0.92	High Similarity	NPC195763
0.92	High Similarity	NPC264550
0.92	High Similarity	NPC142876
0.92	High Similarity	NPC139293
0.92	High Similarity	NPC100985
0.9195	High Similarity	NPC190648
0.9195	High Similarity	NPC126767
0.9195	High Similarity	NPC34802
0.9195	High Similarity	NPC118027
0.9195	High Similarity	NPC312929
0.9195	High Similarity	NPC56433
0.9195	High Similarity	NPC245584
0.9195	High Similarity	NPC289042
0.9184	High Similarity	NPC471417
0.9184	High Similarity	NPC84266
0.9177	High Similarity	NPC218226
0.9167	High Similarity	NPC470694
0.9167	High Similarity	NPC294965
0.9161	High Similarity	NPC36217
0.9161	High Similarity	NPC119224
0.9161	High Similarity	NPC321399
0.9161	High Similarity	NPC474960
0.9156	High Similarity	NPC273843
0.9156	High Similarity	NPC52889
0.9156	High Similarity	NPC78103
0.915	High Similarity	NPC39184
0.915	High Similarity	NPC234255
0.915	High Similarity	NPC67396
0.9145	High Similarity	NPC471982
0.9145	High Similarity	NPC312338
0.9145	High Similarity	NPC40356
0.9145	High Similarity	NPC154683
0.9145	High Similarity	NPC149889
0.9145	High Similarity	NPC164912
0.9145	High Similarity	NPC106976
0.9139	High Similarity	NPC3825
0.9139	High Similarity	NPC472279
0.9139	High Similarity	NPC280295
0.9139	High Similarity	NPC147735
0.9139	High Similarity	NPC290954
0.9139	High Similarity	NPC10467
0.9139	High Similarity	NPC255641
0.9139	High Similarity	NPC88804
0.9133	High Similarity	NPC27221
0.9133	High Similarity	NPC256672
0.9133	High Similarity	NPC7025
0.9128	High Similarity	NPC12377
0.9122	High Similarity	NPC105213
0.9116	High Similarity	NPC284556
0.9116	High Similarity	NPC301178
0.9116	High Similarity	NPC94076
0.9116	High Similarity	NPC182255
0.9108	High Similarity	NPC236132
0.9108	High Similarity	NPC186686
0.9108	High Similarity	NPC207690
0.9108	High Similarity	NPC101769
0.9103	High Similarity	NPC278427
0.9103	High Similarity	NPC66288
0.9097	High Similarity	NPC184755
0.9097	High Similarity	NPC74178
0.9091	High Similarity	NPC472455
0.9091	High Similarity	NPC142339
0.9091	High Similarity	NPC24640
0.9085	High Similarity	NPC192083
0.9085	High Similarity	NPC74924
0.9085	High Similarity	NPC210942
0.9085	High Similarity	NPC298692
0.9085	High Similarity	NPC124714
0.9085	High Similarity	NPC250557
0.9085	High Similarity	NPC213896
0.9085	High Similarity	NPC169990
0.9079	High Similarity	NPC205046
0.9079	High Similarity	NPC78505
0.9079	High Similarity	NPC302783
0.9079	High Similarity	NPC474417
0.9079	High Similarity	NPC72958
0.9079	High Similarity	NPC45291
0.9079	High Similarity	NPC118427
0.9079	High Similarity	NPC19980
0.9079	High Similarity	NPC59162
0.9079	High Similarity	NPC149526
0.9079	High Similarity	NPC473201
0.9079	High Similarity	NPC478148
0.9079	High Similarity	NPC304295
0.9079	High Similarity	NPC232645
0.9073	High Similarity	NPC329933
0.9067	High Similarity	NPC7943
0.9067	High Similarity	NPC125449
0.9067	High Similarity	NPC22005
0.9067	High Similarity	NPC123202
0.9067	High Similarity	NPC188074
0.906	High Similarity	NPC157133
0.9057	High Similarity	NPC474024
0.9054	High Similarity	NPC476054
0.9054	High Similarity	NPC287722
0.9048	High Similarity	NPC259166
0.9048	High Similarity	NPC204985
0.9048	High Similarity	NPC172250
0.9048	High Similarity	NPC213659
0.9048	High Similarity	NPC215311
0.9048	High Similarity	NPC48624
0.9048	High Similarity	NPC144118
0.9048	High Similarity	NPC80962
0.9048	High Similarity	NPC326109
0.9048	High Similarity	NPC219917
0.9048	High Similarity	NPC253822
0.9045	High Similarity	NPC329760
0.9045	High Similarity	NPC201800
0.9045	High Similarity	NPC211107
0.9038	High Similarity	NPC14353
0.9038	High Similarity	NPC228785
0.9038	High Similarity	NPC297212
0.9038	High Similarity	NPC328102
0.9038	High Similarity	NPC476283
0.9038	High Similarity	NPC28241
0.9038	High Similarity	NPC56085
0.9038	High Similarity	NPC471973
0.9032	High Similarity	NPC236796
0.9032	High Similarity	NPC291508
0.9032	High Similarity	NPC472963
0.9032	High Similarity	NPC136674
0.9026	High Similarity	NPC80534
0.9026	High Similarity	NPC113906
0.9026	High Similarity	NPC472280
0.9026	High Similarity	NPC200761
0.9026	High Similarity	NPC45849
0.9026	High Similarity	NPC321779
0.9026	High Similarity	NPC133392
0.9026	High Similarity	NPC168247
0.9026	High Similarity	NPC152951
0.9026	High Similarity	NPC56786
0.9026	High Similarity	NPC117992
0.9026	High Similarity	NPC470327
0.9026	High Similarity	NPC230149
0.9026	High Similarity	NPC477503
0.9026	High Similarity	NPC57674
0.902	High Similarity	NPC100971
0.902	High Similarity	NPC157784
0.902	High Similarity	NPC470337
0.902	High Similarity	NPC51824
0.902	High Similarity	NPC37684
0.902	High Similarity	NPC180944
0.902	High Similarity	NPC113608
0.902	High Similarity	NPC131266
0.902	High Similarity	NPC209487
0.902	High Similarity	NPC269451
0.902	High Similarity	NPC249570
0.902	High Similarity	NPC181209
0.902	High Similarity	NPC63187
0.902	High Similarity	NPC35763

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 NPC93552 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	1017
0.2-0.3	1738
0.3-0.4	2652
0.4-0.5	1823
0.5-0.6	968
0.6-0.7	389
0.7-0.8	125
0.8-0.85	37
0.85-0.9	15
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9085	High Similarity	NPD2393	Clinical (unspecified phase)
0.8805	High Similarity	NPD6232	Discontinued
0.8774	High Similarity	NPD1934	Approved
0.8758	High Similarity	NPD7473	Discontinued
0.8742	High Similarity	NPD1511	Approved
0.8718	High Similarity	NPD2801	Approved
0.8707	High Similarity	NPD1510	Phase 2
0.8645	High Similarity	NPD4380	Phase 2
0.8627	High Similarity	NPD1512	Approved
0.8608	High Similarity	NPD3882	Suspended
0.8599	High Similarity	NPD7819	Suspended
0.8571	High Similarity	NPD1607	Approved
0.8562	High Similarity	NPD4378	Clinical (unspecified phase)
0.8509	High Similarity	NPD6959	Discontinued
0.8456	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD2532	Approved
0.8442	Intermediate Similarity	NPD2534	Approved
0.8442	Intermediate Similarity	NPD2533	Approved
0.8435	Intermediate Similarity	NPD1240	Approved
0.8411	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD3818	Discontinued
0.8354	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6166	Phase 2
0.8354	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7075	Discontinued
0.8313	Intermediate Similarity	NPD3817	Phase 2
0.8313	Intermediate Similarity	NPD5844	Phase 1
0.8311	Intermediate Similarity	NPD943	Approved
0.8289	Intermediate Similarity	NPD1549	Phase 2
0.8278	Intermediate Similarity	NPD2796	Approved
0.8261	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD5494	Approved
0.8204	Intermediate Similarity	NPD7054	Approved
0.8199	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6801	Discontinued
0.8176	Intermediate Similarity	NPD6599	Discontinued
0.8155	Intermediate Similarity	NPD7074	Phase 3
0.8155	Intermediate Similarity	NPD7472	Approved
0.8141	Intermediate Similarity	NPD7390	Discontinued
0.8125	Intermediate Similarity	NPD7411	Suspended
0.8107	Intermediate Similarity	NPD6797	Phase 2
0.8098	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD3750	Approved
0.8059	Intermediate Similarity	NPD7251	Discontinued
0.8039	Intermediate Similarity	NPD2935	Discontinued
0.8025	Intermediate Similarity	NPD6799	Approved
0.8025	Intermediate Similarity	NPD1465	Phase 2
0.7975	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD6559	Discontinued
0.7943	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7768	Phase 2
0.7917	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD7808	Phase 3
0.7907	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD230	Phase 1
0.7888	Intermediate Similarity	NPD3226	Approved
0.7882	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD6651	Approved
0.7831	Intermediate Similarity	NPD6234	Discontinued
0.7831	Intermediate Similarity	NPD919	Approved
0.7806	Intermediate Similarity	NPD6100	Approved
0.7806	Intermediate Similarity	NPD6099	Approved
0.7806	Intermediate Similarity	NPD1551	Phase 2
0.7798	Intermediate Similarity	NPD5710	Approved
0.7798	Intermediate Similarity	NPD5711	Approved
0.7791	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3749	Approved
0.7771	Intermediate Similarity	NPD2800	Approved
0.7764	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2346	Discontinued
0.7753	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD37	Approved
0.7742	Intermediate Similarity	NPD3748	Approved
0.7738	Intermediate Similarity	NPD1247	Approved
0.7722	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD4628	Phase 3
0.7692	Intermediate Similarity	NPD5408	Approved
0.7692	Intermediate Similarity	NPD5405	Approved
0.7692	Intermediate Similarity	NPD5406	Approved
0.7692	Intermediate Similarity	NPD5404	Approved
0.7658	Intermediate Similarity	NPD1243	Approved
0.7654	Intermediate Similarity	NPD5403	Approved
0.7651	Intermediate Similarity	NPD5402	Approved
0.765	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3926	Phase 2
0.7632	Intermediate Similarity	NPD3027	Phase 3
0.761	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD4967	Phase 2
0.7605	Intermediate Similarity	NPD4965	Approved
0.7605	Intermediate Similarity	NPD4966	Approved
0.76	Intermediate Similarity	NPD1470	Approved
0.76	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1201	Approved
0.7561	Intermediate Similarity	NPD7458	Discontinued
0.755	Intermediate Similarity	NPD2798	Approved
0.7546	Intermediate Similarity	NPD920	Approved
0.7531	Intermediate Similarity	NPD5401	Approved
0.7529	Intermediate Similarity	NPD7199	Phase 2
0.7516	Intermediate Similarity	NPD4625	Phase 3
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.7516	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7228	Approved
0.7513	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7003	Approved
0.7486	Intermediate Similarity	NPD5953	Discontinued
0.7484	Intermediate Similarity	NPD1613	Approved
0.7484	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6782	Approved
0.7459	Intermediate Similarity	NPD6777	Approved
0.7459	Intermediate Similarity	NPD6779	Approved
0.7459	Intermediate Similarity	NPD6776	Approved
0.7459	Intermediate Similarity	NPD6778	Approved
0.7459	Intermediate Similarity	NPD6781	Approved
0.7459	Intermediate Similarity	NPD6780	Approved
0.7458	Intermediate Similarity	NPD8312	Approved
0.7458	Intermediate Similarity	NPD8313	Approved
0.7455	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8150	Discontinued
0.7423	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2344	Approved
0.74	Intermediate Similarity	NPD3972	Approved
0.7371	Intermediate Similarity	NPD7286	Phase 2
0.7365	Intermediate Similarity	NPD1651	Approved
0.7362	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2313	Discontinued
0.7355	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7435	Discontinued
0.7314	Intermediate Similarity	NPD3751	Discontinued
0.7303	Intermediate Similarity	NPD1283	Approved
0.7285	Intermediate Similarity	NPD9269	Phase 2
0.7284	Intermediate Similarity	NPD8166	Discontinued
0.7249	Intermediate Similarity	NPD7698	Approved
0.7249	Intermediate Similarity	NPD7696	Phase 3
0.7249	Intermediate Similarity	NPD7697	Approved
0.7239	Intermediate Similarity	NPD2309	Approved
0.7239	Intermediate Similarity	NPD6190	Approved
0.7226	Intermediate Similarity	NPD4908	Phase 1
0.7222	Intermediate Similarity	NPD2654	Approved
0.7216	Intermediate Similarity	NPD7177	Discontinued
0.7215	Intermediate Similarity	NPD447	Suspended
0.7212	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7870	Phase 2
0.7211	Intermediate Similarity	NPD7871	Phase 2
0.7208	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4626	Approved
0.7196	Intermediate Similarity	NPD6823	Phase 2
0.7189	Intermediate Similarity	NPD6534	Approved
0.7189	Intermediate Similarity	NPD4363	Phase 3
0.7189	Intermediate Similarity	NPD6535	Approved
0.7189	Intermediate Similarity	NPD4360	Phase 2
0.7188	Intermediate Similarity	NPD4308	Phase 3
0.7188	Intermediate Similarity	NPD7701	Phase 2
0.7184	Intermediate Similarity	NPD3787	Discontinued
0.7184	Intermediate Similarity	NPD7229	Phase 3
0.7152	Intermediate Similarity	NPD4060	Phase 1
0.7151	Intermediate Similarity	NPD7685	Pre-registration
0.7151	Intermediate Similarity	NPD4361	Phase 2
0.7151	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1203	Approved
0.7143	Intermediate Similarity	NPD5242	Approved
0.7143	Intermediate Similarity	NPD8434	Phase 2
0.7135	Intermediate Similarity	NPD4288	Approved
0.7134	Intermediate Similarity	NPD3268	Approved
0.7134	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3764	Approved
0.7127	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4749	Approved
0.7117	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6832	Phase 2
0.7113	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7874	Approved
0.7107	Intermediate Similarity	NPD1933	Approved
0.7105	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1281	Approved
0.7105	Intermediate Similarity	NPD1610	Phase 2
0.7099	Intermediate Similarity	NPD1471	Phase 3
0.7091	Intermediate Similarity	NPD3300	Phase 2
0.7083	Intermediate Similarity	NPD1653	Approved
0.7081	Intermediate Similarity	NPD7033	Discontinued
0.7078	Intermediate Similarity	NPD1876	Approved
0.7077	Intermediate Similarity	NPD7801	Approved
0.7074	Intermediate Similarity	NPD7699	Phase 2
0.7074	Intermediate Similarity	NPD7700	Phase 2
0.7067	Intermediate Similarity	NPD1548	Phase 1
0.7066	Intermediate Similarity	NPD6273	Approved
0.7056	Intermediate Similarity	NPD7240	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