NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	542.12
Volume:	527.089
LogP:	4.79
LogD:	3.373
LogS:	-6.606
# Rotatable Bonds:	4
TPSA:	162.98
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.225
Synthetic Accessibility Score:	3.73
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.652
MDCK Permeability:	7.781574822729453e-06
Pgp-inhibitor:	0.028
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.404
20% Bioavailability (F20%):	0.835
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	98.56614685058594%
Volume Distribution (VD):	0.385
Pgp-substrate:	2.320474147796631%

ADMET: Metabolism

CYP1A2-inhibitor:	0.458
CYP1A2-substrate:	0.11
CYP2C19-inhibitor:	0.959
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.926
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.09
CYP2D6-substrate:	0.62
CYP3A4-inhibitor:	0.589
CYP3A4-substrate:	0.118

ADMET: Excretion

Clearance (CL):	13.913
Half-life (T1/2):	0.431

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.054
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.628
Rat Oral Acute Toxicity:	0.965
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.948
Carcinogencity:	0.242
Eye Corrosion:	0.003
Eye Irritation:	0.906
Respiratory Toxicity:	0.328

Download Data

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

Natural Product: NPC477841

Natural Product ID:	NPC477841
*Common Name:**	2,3,2'',3''-Tetrahydroochnaflavone
IUPAC Name:	2-[4-[5-(5,7-dihydroxy-4-oxo-2,3-dihydrochromen-2-yl)-2-hydroxyphenoxy]phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
Synonyms:	2,3,2',3'-Tetrahydroochnaflavone
Standard InCHIKey:	XEODGBSMXJKQNI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H22O10/c31-16-8-20(34)29-22(36)12-24(39-27(29)10-16)14-1-4-18(5-2-14)38-26-7-15(3-6-19(26)33)25-13-23(37)30-21(35)9-17(32)11-28(30)40-25/h1-11,24-25,31-35H,12-13H2
SMILES:	C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)OC4=C(C=CC(=C4)C5CC(=O)C6=C(C=C(C=C6O5)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11478288
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO21239	Quintinia acutifolia	Species	Paracryphiaceae	Eukaryota	Leaves	Charleston, New Zealand	1997-JAN	PMID[15104507]
NPO21239	Quintinia acutifolia	Species	Paracryphiaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	8.2	ug/ml	PMID[15104507]

☑ 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 NPC477841 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	448
0.1-0.2	1816
0.2-0.3	4656
0.3-0.4	10878
0.4-0.5	6796
0.5-0.6	3712
0.6-0.7	4768
0.7-0.8	5306
0.8-0.85	2610
0.85-0.9	1419
0.9-0.95	274
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9871	High Similarity	NPC477840
0.987	High Similarity	NPC219927
0.9618	High Similarity	NPC125039
0.9618	High Similarity	NPC7688
0.9618	High Similarity	NPC7154
0.9618	High Similarity	NPC36916
0.9618	High Similarity	NPC58223
0.9618	High Similarity	NPC72787
0.9618	High Similarity	NPC36
0.956	High Similarity	NPC475212
0.9557	High Similarity	NPC224851
0.9551	High Similarity	NPC113163
0.9551	High Similarity	NPC66618
0.9551	High Similarity	NPC288131
0.9551	High Similarity	NPC84324
0.9551	High Similarity	NPC305987
0.9551	High Similarity	NPC165970
0.9551	High Similarity	NPC158188
0.95	High Similarity	NPC476365
0.9497	High Similarity	NPC14662
0.9487	High Similarity	NPC101731
0.9484	High Similarity	NPC112954
0.9441	High Similarity	NPC186847
0.9441	High Similarity	NPC472454
0.9441	High Similarity	NPC257667
0.9434	High Similarity	NPC171985
0.9434	High Similarity	NPC320741
0.9427	High Similarity	NPC142252
0.9423	High Similarity	NPC476410
0.9423	High Similarity	NPC284127
0.9423	High Similarity	NPC172202
0.9416	High Similarity	NPC18727
0.9375	High Similarity	NPC243877
0.9367	High Similarity	NPC476247
0.9359	High Similarity	NPC183
0.9359	High Similarity	NPC183851
0.9359	High Similarity	NPC63454
0.9351	High Similarity	NPC219582
0.9351	High Similarity	NPC236637
0.9351	High Similarity	NPC302950
0.9317	High Similarity	NPC107627
0.9313	High Similarity	NPC272560
0.9308	High Similarity	NPC272064
0.9304	High Similarity	NPC471211
0.9304	High Similarity	NPC26326
0.9304	High Similarity	NPC196179
0.9304	High Similarity	NPC34089
0.9304	High Similarity	NPC471212
0.9304	High Similarity	NPC472632
0.9304	High Similarity	NPC471210
0.9299	High Similarity	NPC53545
0.9299	High Similarity	NPC117418
0.9295	High Similarity	NPC195796
0.9295	High Similarity	NPC278778
0.9295	High Similarity	NPC291878
0.9295	High Similarity	NPC35038
0.9273	High Similarity	NPC324742
0.9255	High Similarity	NPC295082
0.9255	High Similarity	NPC260266
0.9245	High Similarity	NPC474033
0.9245	High Similarity	NPC474034
0.9241	High Similarity	NPC192686
0.9241	High Similarity	NPC118256
0.9241	High Similarity	NPC174953
0.9241	High Similarity	NPC119209
0.9236	High Similarity	NPC472598
0.9236	High Similarity	NPC156057
0.9236	High Similarity	NPC474836
0.9236	High Similarity	NPC471209
0.9236	High Similarity	NPC27337
0.9236	High Similarity	NPC48208
0.9236	High Similarity	NPC291508
0.9236	High Similarity	NPC471515
0.9236	High Similarity	NPC185526
0.9236	High Similarity	NPC475267
0.9236	High Similarity	NPC162869
0.9236	High Similarity	NPC474055
0.9236	High Similarity	NPC471479
0.9236	High Similarity	NPC474208
0.9231	High Similarity	NPC45849
0.9231	High Similarity	NPC200761
0.9231	High Similarity	NPC470327
0.9231	High Similarity	NPC477503
0.9226	High Similarity	NPC472912
0.9221	High Similarity	NPC338131
0.9216	High Similarity	NPC188679
0.9216	High Similarity	NPC321011
0.9216	High Similarity	NPC294852
0.9212	High Similarity	NPC265380
0.9202	High Similarity	NPC67134
0.9202	High Similarity	NPC4200
0.9202	High Similarity	NPC47140
0.9202	High Similarity	NPC81332
0.9202	High Similarity	NPC262580
0.9202	High Similarity	NPC212038
0.9202	High Similarity	NPC289396
0.9202	High Similarity	NPC271848
0.9193	High Similarity	NPC471213
0.9193	High Similarity	NPC5778
0.9193	High Similarity	NPC236934
0.9187	High Similarity	NPC29830
0.9182	High Similarity	NPC289771
0.9182	High Similarity	NPC474038
0.9182	High Similarity	NPC472634
0.9182	High Similarity	NPC471499
0.9182	High Similarity	NPC173137
0.9182	High Similarity	NPC134783
0.9177	High Similarity	NPC123544
0.9177	High Similarity	NPC190487
0.9177	High Similarity	NPC154304
0.9177	High Similarity	NPC473990
0.9172	High Similarity	NPC470328
0.9172	High Similarity	NPC235165
0.9172	High Similarity	NPC250922
0.9172	High Similarity	NPC326037
0.9172	High Similarity	NPC255106
0.9172	High Similarity	NPC13858
0.9172	High Similarity	NPC471500
0.9172	High Similarity	NPC320825
0.9172	High Similarity	NPC209614
0.9172	High Similarity	NPC472626
0.9167	High Similarity	NPC213896
0.9167	High Similarity	NPC192083
0.9157	High Similarity	NPC185275
0.9156	High Similarity	NPC183959
0.9156	High Similarity	NPC1612
0.9141	High Similarity	NPC44328
0.9141	High Similarity	NPC279209
0.9141	High Similarity	NPC105095
0.9141	High Similarity	NPC231194
0.9141	High Similarity	NPC79056
0.9141	High Similarity	NPC102277
0.9141	High Similarity	NPC177731
0.9141	High Similarity	NPC51326
0.9136	High Similarity	NPC473818
0.9136	High Similarity	NPC45400
0.913	High Similarity	NPC293319
0.913	High Similarity	NPC62261
0.913	High Similarity	NPC224280
0.9125	High Similarity	NPC472635
0.9119	High Similarity	NPC472630
0.9119	High Similarity	NPC287328
0.9119	High Similarity	NPC470326
0.9119	High Similarity	NPC475784
0.9119	High Similarity	NPC282009
0.9119	High Similarity	NPC472631
0.9119	High Similarity	NPC472624
0.9119	High Similarity	NPC36217
0.9119	High Similarity	NPC53889
0.9119	High Similarity	NPC188967
0.9114	High Similarity	NPC38779
0.9114	High Similarity	NPC284820
0.9114	High Similarity	NPC223787
0.9114	High Similarity	NPC472914
0.9114	High Similarity	NPC289322
0.9114	High Similarity	NPC245758
0.9114	High Similarity	NPC129684
0.9114	High Similarity	NPC52530
0.9114	High Similarity	NPC472911
0.9114	High Similarity	NPC160512
0.9114	High Similarity	NPC210084
0.9114	High Similarity	NPC222814
0.9114	High Similarity	NPC472910
0.9114	High Similarity	NPC299520
0.9114	High Similarity	NPC67876
0.9114	High Similarity	NPC114179
0.9114	High Similarity	NPC156818
0.9114	High Similarity	NPC473272
0.9114	High Similarity	NPC99597
0.9114	High Similarity	NPC472913
0.9114	High Similarity	NPC96167
0.9114	High Similarity	NPC68324
0.9108	High Similarity	NPC37392
0.9108	High Similarity	NPC134171
0.9108	High Similarity	NPC226025
0.9108	High Similarity	NPC201227
0.9108	High Similarity	NPC258474
0.9108	High Similarity	NPC300668
0.9108	High Similarity	NPC67396
0.9108	High Similarity	NPC321779
0.9103	High Similarity	NPC19721
0.9103	High Similarity	NPC246162
0.9103	High Similarity	NPC9743
0.9103	High Similarity	NPC106976
0.9103	High Similarity	NPC36835
0.9103	High Similarity	NPC240476
0.9103	High Similarity	NPC477231
0.9103	High Similarity	NPC260979
0.9103	High Similarity	NPC61506
0.9103	High Similarity	NPC260491
0.9103	High Similarity	NPC257648
0.9096	High Similarity	NPC476622
0.9096	High Similarity	NPC476620
0.9096	High Similarity	NPC476621
0.9096	High Similarity	NPC476623
0.9096	High Similarity	NPC476619
0.9096	High Similarity	NPC476618
0.9091	High Similarity	NPC3036
0.9085	High Similarity	NPC476370
0.9085	High Similarity	NPC256760

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 NPC477841 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	427
0.1-0.2	948
0.2-0.3	1860
0.3-0.4	2629
0.4-0.5	1733
0.5-0.6	969
0.6-0.7	418
0.7-0.8	114
0.8-0.85	28
0.85-0.9	17
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9618	High Similarity	NPD6167	Clinical (unspecified phase)
0.9618	High Similarity	NPD6166	Phase 2
0.9618	High Similarity	NPD6168	Clinical (unspecified phase)
0.9351	High Similarity	NPD1934	Approved
0.9167	High Similarity	NPD2393	Clinical (unspecified phase)
0.9141	High Similarity	NPD7074	Phase 3
0.908	High Similarity	NPD7054	Approved
0.9051	High Similarity	NPD4868	Clinical (unspecified phase)
0.9024	High Similarity	NPD7472	Approved
0.897	High Similarity	NPD7993	Clinical (unspecified phase)
0.8924	High Similarity	NPD2801	Approved
0.8855	High Similarity	NPD6797	Phase 2
0.8831	High Similarity	NPD1511	Approved
0.8827	High Similarity	NPD6959	Discontinued
0.8802	High Similarity	NPD7251	Discontinued
0.8788	High Similarity	NPD3818	Discontinued
0.875	High Similarity	NPD7808	Phase 3
0.8734	High Similarity	NPD4380	Phase 2
0.8718	High Similarity	NPD1512	Approved
0.8696	High Similarity	NPD3882	Suspended
0.8642	High Similarity	NPD4381	Clinical (unspecified phase)
0.8639	High Similarity	NPD4338	Clinical (unspecified phase)
0.8634	High Similarity	NPD3817	Phase 2
0.8562	High Similarity	NPD1552	Clinical (unspecified phase)
0.8562	High Similarity	NPD1550	Clinical (unspecified phase)
0.8537	High Similarity	NPD5494	Approved
0.8519	High Similarity	NPD8443	Clinical (unspecified phase)
0.8506	High Similarity	NPD1549	Phase 2
0.8415	Intermediate Similarity	NPD7075	Discontinued
0.8402	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1465	Phase 2
0.8333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7411	Suspended
0.8323	Intermediate Similarity	NPD6232	Discontinued
0.8302	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD5844	Phase 1
0.8284	Intermediate Similarity	NPD7473	Discontinued
0.8232	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1510	Phase 2
0.8141	Intermediate Similarity	NPD2796	Approved
0.8121	Intermediate Similarity	NPD7819	Suspended
0.8072	Intermediate Similarity	NPD5402	Approved
0.8061	Intermediate Similarity	NPD6801	Discontinued
0.8052	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1613	Approved
0.8046	Intermediate Similarity	NPD6559	Discontinued
0.8034	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7768	Phase 2
0.8012	Intermediate Similarity	NPD6799	Approved
0.7976	Intermediate Similarity	NPD3749	Approved
0.7975	Intermediate Similarity	NPD5403	Approved
0.7955	Intermediate Similarity	NPD8312	Approved
0.7955	Intermediate Similarity	NPD8313	Approved
0.7935	Intermediate Similarity	NPD943	Approved
0.7935	Intermediate Similarity	NPD1240	Approved
0.7908	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD5401	Approved
0.7849	Intermediate Similarity	NPD3926	Phase 2
0.7843	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1607	Approved
0.7831	Intermediate Similarity	NPD6599	Discontinued
0.7791	Intermediate Similarity	NPD7390	Discontinued
0.7791	Intermediate Similarity	NPD3787	Discontinued
0.7742	Intermediate Similarity	NPD3027	Phase 3
0.7733	Intermediate Similarity	NPD7199	Phase 2
0.7716	Intermediate Similarity	NPD3750	Approved
0.7714	Intermediate Similarity	NPD7228	Approved
0.7714	Intermediate Similarity	NPD3751	Discontinued
0.7692	Intermediate Similarity	NPD8455	Phase 2
0.7654	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1247	Approved
0.7616	Intermediate Similarity	NPD6234	Discontinued
0.7616	Intermediate Similarity	NPD919	Approved
0.7605	Intermediate Similarity	NPD1653	Approved
0.7593	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1551	Phase 2
0.7576	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4908	Phase 1
0.7561	Intermediate Similarity	NPD6190	Approved
0.7547	Intermediate Similarity	NPD230	Phase 1
0.753	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7469	Intermediate Similarity	NPD2935	Discontinued
0.7468	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2800	Approved
0.7438	Intermediate Similarity	NPD447	Suspended
0.7427	Intermediate Similarity	NPD37	Approved
0.7425	Intermediate Similarity	NPD2532	Approved
0.7425	Intermediate Similarity	NPD2534	Approved
0.7425	Intermediate Similarity	NPD2533	Approved
0.7407	Intermediate Similarity	NPD3748	Approved
0.7407	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4966	Approved
0.7399	Intermediate Similarity	NPD4965	Approved
0.7399	Intermediate Similarity	NPD4967	Phase 2
0.7394	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6777	Approved
0.7368	Intermediate Similarity	NPD6780	Approved
0.7368	Intermediate Similarity	NPD6778	Approved
0.7368	Intermediate Similarity	NPD6776	Approved
0.7368	Intermediate Similarity	NPD6781	Approved
0.7368	Intermediate Similarity	NPD6782	Approved
0.7368	Intermediate Similarity	NPD6779	Approved
0.7362	Intermediate Similarity	NPD6099	Approved
0.7362	Intermediate Similarity	NPD6100	Approved
0.7353	Intermediate Similarity	NPD3226	Approved
0.7348	Intermediate Similarity	NPD7685	Pre-registration
0.7338	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1933	Approved
0.7317	Intermediate Similarity	NPD2344	Approved
0.7293	Intermediate Similarity	NPD5953	Discontinued
0.7284	Intermediate Similarity	NPD6651	Approved
0.7278	Intermediate Similarity	NPD9494	Approved
0.7259	Intermediate Similarity	NPD7783	Phase 2
0.7259	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7698	Approved
0.7254	Intermediate Similarity	NPD7696	Phase 3
0.7254	Intermediate Similarity	NPD7435	Discontinued
0.7254	Intermediate Similarity	NPD7697	Approved
0.7253	Intermediate Similarity	NPD7240	Approved
0.7251	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6798	Discontinued
0.7244	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD8150	Discontinued
0.7235	Intermediate Similarity	NPD920	Approved
0.7226	Intermediate Similarity	NPD1610	Phase 2
0.7219	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7870	Phase 2
0.7216	Intermediate Similarity	NPD7871	Phase 2
0.7213	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7266	Discontinued
0.7202	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4360	Phase 2
0.7196	Intermediate Similarity	NPD4363	Phase 3
0.7195	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7701	Phase 2
0.7186	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7286	Phase 2
0.7152	Intermediate Similarity	NPD5404	Approved
0.7152	Intermediate Similarity	NPD5405	Approved
0.7152	Intermediate Similarity	NPD5408	Approved
0.7152	Intermediate Similarity	NPD1203	Approved
0.7152	Intermediate Similarity	NPD5406	Approved
0.7151	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD2309	Approved
0.7143	Intermediate Similarity	NPD7584	Approved
0.7135	Intermediate Similarity	NPD8127	Discontinued
0.7126	Intermediate Similarity	NPD1243	Approved
0.7125	Intermediate Similarity	NPD6832	Phase 2
0.712	Intermediate Similarity	NPD7549	Discontinued
0.7113	Intermediate Similarity	NPD6823	Phase 2
0.7108	Intermediate Similarity	NPD2346	Discontinued
0.7105	Intermediate Similarity	NPD6534	Approved
0.7105	Intermediate Similarity	NPD6535	Approved
0.7099	Intermediate Similarity	NPD6233	Phase 2
0.7091	Intermediate Similarity	NPD2799	Discontinued
0.7091	Intermediate Similarity	NPD7033	Discontinued
0.7083	Intermediate Similarity	NPD7700	Phase 2
0.7083	Intermediate Similarity	NPD7699	Phase 2
0.7083	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1548	Phase 1
0.7074	Intermediate Similarity	NPD4287	Approved
0.7063	Intermediate Similarity	NPD2861	Phase 2
0.7059	Intermediate Similarity	NPD8434	Phase 2
0.7056	Intermediate Similarity	NPD5242	Approved
0.7045	Intermediate Similarity	NPD5353	Approved
0.7043	Intermediate Similarity	NPD8053	Approved
0.7043	Intermediate Similarity	NPD8054	Approved
0.7035	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7874	Approved
0.7029	Intermediate Similarity	NPD6844	Discontinued
0.7012	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5710	Approved
0.7	Intermediate Similarity	NPD7229	Phase 3
0.7	Intermediate Similarity	NPD7801	Approved
0.7	Intermediate Similarity	NPD5711	Approved
0.699	Remote Similarity	NPD7680	Approved
0.6982	Remote Similarity	NPD8166	Discontinued
0.6973	Remote Similarity	NPD7039	Approved
0.6973	Remote Similarity	NPD7038	Approved
0.6971	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD9269	Phase 2
0.6959	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7213	Phase 3
0.6959	Remote Similarity	NPD7212	Phase 2
0.6957	Remote Similarity	NPD3018	Phase 2
0.6954	Remote Similarity	NPD8320	Phase 1
0.6954	Remote Similarity	NPD8319	Approved
0.694	Remote Similarity	NPD7177	Discontinued
0.6933	Remote Similarity	NPD3268	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