NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	570.15
Volume:	561.681
LogP:	5.785
LogD:	3.746
LogS:	-6.995
# Rotatable Bonds:	6
TPSA:	140.98
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.252
Synthetic Accessibility Score:	3.678
Fsp3:	0.188
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.18
MDCK Permeability:	3.456117701716721e-05
Pgp-inhibitor:	0.872
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.12
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.756

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	97.59709167480469%
Volume Distribution (VD):	0.332
Pgp-substrate:	1.548883080482483%

ADMET: Metabolism

CYP1A2-inhibitor:	0.176
CYP1A2-substrate:	0.933
CYP2C19-inhibitor:	0.963
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.939
CYP2C9-substrate:	0.967
CYP2D6-inhibitor:	0.063
CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.58
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	8.931
Half-life (T1/2):	0.084

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.08
Drug-inuced Liver Injury (DILI):	0.965
AMES Toxicity:	0.665
Rat Oral Acute Toxicity:	0.967
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.885
Carcinogencity:	0.213
Eye Corrosion:	0.003
Eye Irritation:	0.865
Respiratory Toxicity:	0.827

Download Data

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

Natural Product: NPC477840

Natural Product ID:	NPC477840
*Common Name:**	7,7''-Di-O-methyl-2,3,2'',3''-tetrahydroochnaflavone
IUPAC Name:	5-hydroxy-2-[4-[2-hydroxy-5-(5-hydroxy-7-methoxy-4-oxo-2,3-dihydrochromen-2-yl)phenoxy]phenyl]-7-methoxy-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	ILTSXACDAGDHTJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C32H26O10/c1-38-19-10-22(34)31-24(36)14-26(41-29(31)12-19)16-3-6-18(7-4-16)40-28-9-17(5-8-21(28)33)27-15-25(37)32-23(35)11-20(39-2)13-30(32)42-27/h3-13,26-27,33-35H,14-15H2,1-2H3
SMILES:	COC1=CC(=C2C(=O)CC(OC2=C1)C3=CC=C(C=C3)OC4=C(C=CC(=C4)C5CC(=O)C6=C(C=C(C=C6O5)OC)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11786419
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	=	8.7	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 NPC477840 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	427
0.1-0.2	1637
0.2-0.3	4100
0.3-0.4	10283
0.4-0.5	7952
0.5-0.6	3475
0.6-0.7	4750
0.7-0.8	5455
0.8-0.85	2591
0.85-0.9	1715
0.9-0.95	297
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9871	High Similarity	NPC477841
0.9744	High Similarity	NPC219927
0.9686	High Similarity	NPC475212
0.9625	High Similarity	NPC476365
0.962	High Similarity	NPC36916
0.962	High Similarity	NPC58223
0.962	High Similarity	NPC7688
0.962	High Similarity	NPC36
0.962	High Similarity	NPC7154
0.962	High Similarity	NPC72787
0.962	High Similarity	NPC125039
0.9554	High Similarity	NPC113163
0.9554	High Similarity	NPC66618
0.9554	High Similarity	NPC288131
0.9554	High Similarity	NPC305987
0.9554	High Similarity	NPC165970
0.9554	High Similarity	NPC158188
0.9554	High Similarity	NPC84324
0.95	High Similarity	NPC14662
0.949	High Similarity	NPC101731
0.9437	High Similarity	NPC224851
0.943	High Similarity	NPC142252
0.9427	High Similarity	NPC476410
0.9427	High Similarity	NPC284127
0.9427	High Similarity	NPC172202
0.9419	High Similarity	NPC18727
0.9394	High Similarity	NPC324742
0.9379	High Similarity	NPC243877
0.9371	High Similarity	NPC476247
0.9363	High Similarity	NPC63454
0.9363	High Similarity	NPC183851
0.9363	High Similarity	NPC183
0.9363	High Similarity	NPC112954
0.9355	High Similarity	NPC302950
0.9355	High Similarity	NPC219582
0.9355	High Similarity	NPC236637
0.9325	High Similarity	NPC186847
0.9325	High Similarity	NPC257667
0.9325	High Similarity	NPC472454
0.9317	High Similarity	NPC171985
0.9317	High Similarity	NPC320741
0.9313	High Similarity	NPC272064
0.9308	High Similarity	NPC471211
0.9308	High Similarity	NPC26326
0.9308	High Similarity	NPC471212
0.9308	High Similarity	NPC472632
0.9308	High Similarity	NPC471210
0.9299	High Similarity	NPC195796
0.9299	High Similarity	NPC291878
0.9299	High Similarity	NPC35038
0.9299	High Similarity	NPC278778
0.9277	High Similarity	NPC185275
0.9259	High Similarity	NPC295082
0.925	High Similarity	NPC474034
0.925	High Similarity	NPC474033
0.9245	High Similarity	NPC192686
0.9245	High Similarity	NPC118256
0.9245	High Similarity	NPC188967
0.9245	High Similarity	NPC119209
0.9245	High Similarity	NPC174953
0.9241	High Similarity	NPC162869
0.9241	High Similarity	NPC471515
0.9241	High Similarity	NPC474208
0.9241	High Similarity	NPC471209
0.9241	High Similarity	NPC474055
0.9241	High Similarity	NPC471479
0.9241	High Similarity	NPC472598
0.9241	High Similarity	NPC156057
0.9241	High Similarity	NPC475267
0.9241	High Similarity	NPC474836
0.9241	High Similarity	NPC27337
0.9241	High Similarity	NPC48208
0.9241	High Similarity	NPC291508
0.9236	High Similarity	NPC45849
0.9236	High Similarity	NPC200761
0.9236	High Similarity	NPC470327
0.9236	High Similarity	NPC477503
0.9231	High Similarity	NPC472912
0.9226	High Similarity	NPC338131
0.9217	High Similarity	NPC265380
0.9207	High Similarity	NPC476370
0.9207	High Similarity	NPC4200
0.9202	High Similarity	NPC107627
0.9198	High Similarity	NPC272560
0.9198	High Similarity	NPC236934
0.9198	High Similarity	NPC5778
0.9198	High Similarity	NPC471213
0.9187	High Similarity	NPC196179
0.9187	High Similarity	NPC474038
0.9187	High Similarity	NPC34089
0.9187	High Similarity	NPC472634
0.9187	High Similarity	NPC471499
0.9187	High Similarity	NPC173137
0.9187	High Similarity	NPC134783
0.9182	High Similarity	NPC154304
0.9182	High Similarity	NPC473990
0.9182	High Similarity	NPC117418
0.9182	High Similarity	NPC190487
0.9182	High Similarity	NPC53545
0.9177	High Similarity	NPC235165
0.9177	High Similarity	NPC471500
0.9177	High Similarity	NPC470328
0.9177	High Similarity	NPC255106
0.9177	High Similarity	NPC209614
0.9177	High Similarity	NPC326037
0.9177	High Similarity	NPC13858
0.9177	High Similarity	NPC320825
0.9177	High Similarity	NPC472626
0.9177	High Similarity	NPC250922
0.9172	High Similarity	NPC192083
0.9172	High Similarity	NPC213896
0.9167	High Similarity	NPC150977
0.9162	High Similarity	NPC471030
0.9152	High Similarity	NPC476374
0.9146	High Similarity	NPC79056
0.9146	High Similarity	NPC44328
0.9146	High Similarity	NPC105095
0.9146	High Similarity	NPC231194
0.9146	High Similarity	NPC102277
0.9146	High Similarity	NPC177731
0.9146	High Similarity	NPC51326
0.9146	High Similarity	NPC279209
0.9141	High Similarity	NPC260266
0.9136	High Similarity	NPC293319
0.9136	High Similarity	NPC62261
0.9136	High Similarity	NPC224280
0.913	High Similarity	NPC472635
0.913	High Similarity	NPC476371
0.913	High Similarity	NPC476372
0.913	High Similarity	NPC201800
0.9125	High Similarity	NPC472630
0.9125	High Similarity	NPC472624
0.9125	High Similarity	NPC36217
0.9125	High Similarity	NPC287328
0.9125	High Similarity	NPC470326
0.9125	High Similarity	NPC475784
0.9125	High Similarity	NPC282009
0.9125	High Similarity	NPC472631
0.9125	High Similarity	NPC53889
0.9119	High Similarity	NPC284820
0.9119	High Similarity	NPC223787
0.9119	High Similarity	NPC129684
0.9119	High Similarity	NPC185526
0.9119	High Similarity	NPC472914
0.9119	High Similarity	NPC99597
0.9119	High Similarity	NPC472913
0.9119	High Similarity	NPC245758
0.9119	High Similarity	NPC271741
0.9119	High Similarity	NPC52530
0.9119	High Similarity	NPC472911
0.9119	High Similarity	NPC210084
0.9119	High Similarity	NPC222814
0.9119	High Similarity	NPC472910
0.9119	High Similarity	NPC299520
0.9119	High Similarity	NPC287789
0.9119	High Similarity	NPC473272
0.9119	High Similarity	NPC96167
0.9119	High Similarity	NPC67876
0.9114	High Similarity	NPC67396
0.9114	High Similarity	NPC37392
0.9114	High Similarity	NPC321779
0.9114	High Similarity	NPC226025
0.9108	High Similarity	NPC106976
0.9108	High Similarity	NPC477231
0.9108	High Similarity	NPC260979
0.9108	High Similarity	NPC257648
0.9107	High Similarity	NPC117668
0.9097	High Similarity	NPC188679
0.9097	High Similarity	NPC294852
0.9097	High Similarity	NPC321011
0.9096	High Similarity	NPC99591
0.9091	High Similarity	NPC81332
0.9091	High Similarity	NPC271848
0.9091	High Similarity	NPC256760
0.9091	High Similarity	NPC262580
0.9091	High Similarity	NPC67134
0.9091	High Similarity	NPC212038
0.9091	High Similarity	NPC289396
0.9091	High Similarity	NPC174700
0.9091	High Similarity	NPC47140
0.9085	High Similarity	NPC209296
0.9085	High Similarity	NPC188079
0.9085	High Similarity	NPC229687
0.9085	High Similarity	NPC195257
0.9085	High Similarity	NPC293629
0.9085	High Similarity	NPC300307
0.9085	High Similarity	NPC43587
0.908	High Similarity	NPC477517
0.908	High Similarity	NPC115674
0.908	High Similarity	NPC210073
0.9074	High Similarity	NPC29830
0.9074	High Similarity	NPC472625
0.9074	High Similarity	NPC186686
0.9068	High Similarity	NPC266314
0.9068	High Similarity	NPC301256
0.9068	High Similarity	NPC289771
0.9068	High Similarity	NPC312273
0.9068	High Similarity	NPC112418
0.9064	High Similarity	NPC473618
0.9062	High Similarity	NPC87317

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 NPC477840 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	377
0.1-0.2	933
0.2-0.3	1768
0.3-0.4	2654
0.4-0.5	1777
0.5-0.6	992
0.6-0.7	467
0.7-0.8	129
0.8-0.85	29
0.85-0.9	18
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.962	High Similarity	NPD6167	Clinical (unspecified phase)
0.962	High Similarity	NPD6166	Phase 2
0.962	High Similarity	NPD6168	Clinical (unspecified phase)
0.9355	High Similarity	NPD1934	Approved
0.9172	High Similarity	NPD2393	Clinical (unspecified phase)
0.9146	High Similarity	NPD7074	Phase 3
0.9085	High Similarity	NPD7054	Approved
0.903	High Similarity	NPD7472	Approved
0.8976	High Similarity	NPD7993	Clinical (unspecified phase)
0.8938	High Similarity	NPD4868	Clinical (unspecified phase)
0.8931	High Similarity	NPD2801	Approved
0.8869	High Similarity	NPD7808	Phase 3
0.8862	High Similarity	NPD6797	Phase 2
0.8834	High Similarity	NPD6959	Discontinued
0.881	High Similarity	NPD7251	Discontinued
0.8718	High Similarity	NPD1511	Approved
0.8704	High Similarity	NPD3882	Suspended
0.8683	High Similarity	NPD3818	Discontinued
0.8642	High Similarity	NPD3817	Phase 2
0.8642	High Similarity	NPD8443	Clinical (unspecified phase)
0.8625	High Similarity	NPD4380	Phase 2
0.8608	High Similarity	NPD1512	Approved
0.8545	High Similarity	NPD5494	Approved
0.8538	High Similarity	NPD4338	Clinical (unspecified phase)
0.8537	High Similarity	NPD4381	Clinical (unspecified phase)
0.8521	High Similarity	NPD7804	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD7075	Discontinued
0.8397	Intermediate Similarity	NPD1549	Phase 2
0.8344	Intermediate Similarity	NPD7411	Suspended
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8313	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD5844	Phase 1
0.8294	Intermediate Similarity	NPD7473	Discontinued
0.8242	Intermediate Similarity	NPD7819	Suspended
0.8242	Intermediate Similarity	NPD1465	Phase 2
0.8242	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD2796	Approved
0.8146	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7768	Phase 2
0.8089	Intermediate Similarity	NPD1510	Phase 2
0.8072	Intermediate Similarity	NPD6801	Discontinued
0.8057	Intermediate Similarity	NPD6559	Discontinued
0.8025	Intermediate Similarity	NPD6799	Approved
0.7976	Intermediate Similarity	NPD5402	Approved
0.7966	Intermediate Similarity	NPD8313	Approved
0.7966	Intermediate Similarity	NPD8312	Approved
0.7949	Intermediate Similarity	NPD1240	Approved
0.7949	Intermediate Similarity	NPD1613	Approved
0.7949	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD3749	Approved
0.7879	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD5403	Approved
0.7861	Intermediate Similarity	NPD3926	Phase 2
0.7848	Intermediate Similarity	NPD1607	Approved
0.7844	Intermediate Similarity	NPD6599	Discontinued
0.7834	Intermediate Similarity	NPD943	Approved
0.7806	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7390	Discontinued
0.776	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD5401	Approved
0.7756	Intermediate Similarity	NPD3027	Phase 3
0.7746	Intermediate Similarity	NPD7199	Phase 2
0.7742	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7228	Approved
0.7706	Intermediate Similarity	NPD8455	Phase 2
0.7701	Intermediate Similarity	NPD3787	Discontinued
0.768	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD1247	Approved
0.763	Intermediate Similarity	NPD6234	Discontinued
0.763	Intermediate Similarity	NPD919	Approved
0.7627	Intermediate Similarity	NPD3751	Discontinued
0.7622	Intermediate Similarity	NPD3750	Approved
0.7617	Intermediate Similarity	NPD8151	Discontinued
0.7607	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD4908	Phase 1
0.7562	Intermediate Similarity	NPD230	Phase 1
0.7545	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD4628	Phase 3
0.7515	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1551	Phase 2
0.7485	Intermediate Similarity	NPD2935	Discontinued
0.7484	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6190	Approved
0.7459	Intermediate Similarity	NPD7685	Pre-registration
0.7455	Intermediate Similarity	NPD2800	Approved
0.7453	Intermediate Similarity	NPD447	Suspended
0.7442	Intermediate Similarity	NPD37	Approved
0.744	Intermediate Similarity	NPD2533	Approved
0.744	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD2534	Approved
0.744	Intermediate Similarity	NPD2532	Approved
0.7414	Intermediate Similarity	NPD4965	Approved
0.7414	Intermediate Similarity	NPD4967	Phase 2
0.7414	Intermediate Similarity	NPD4966	Approved
0.7382	Intermediate Similarity	NPD6781	Approved
0.7382	Intermediate Similarity	NPD6780	Approved
0.7382	Intermediate Similarity	NPD6778	Approved
0.7382	Intermediate Similarity	NPD6779	Approved
0.7382	Intermediate Similarity	NPD6776	Approved
0.7382	Intermediate Similarity	NPD6777	Approved
0.7382	Intermediate Similarity	NPD6782	Approved
0.7378	Intermediate Similarity	NPD6100	Approved
0.7378	Intermediate Similarity	NPD6099	Approved
0.7368	Intermediate Similarity	NPD3226	Approved
0.736	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7783	Phase 2
0.7358	Intermediate Similarity	NPD7698	Approved
0.7358	Intermediate Similarity	NPD7697	Approved
0.7358	Intermediate Similarity	NPD7696	Phase 3
0.7351	Intermediate Similarity	NPD8150	Discontinued
0.7346	Intermediate Similarity	NPD1933	Approved
0.7333	Intermediate Similarity	NPD2344	Approved
0.732	Intermediate Similarity	NPD7870	Phase 2
0.732	Intermediate Similarity	NPD7871	Phase 2
0.7317	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3748	Approved
0.7308	Intermediate Similarity	NPD5953	Discontinued
0.7301	Intermediate Similarity	NPD6651	Approved
0.7296	Intermediate Similarity	NPD7701	Phase 2
0.7296	Intermediate Similarity	NPD9494	Approved
0.7268	Intermediate Similarity	NPD7240	Approved
0.7268	Intermediate Similarity	NPD7435	Discontinued
0.7267	Intermediate Similarity	NPD6798	Discontinued
0.7261	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD920	Approved
0.7247	Intermediate Similarity	NPD8127	Discontinued
0.7244	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7266	Discontinued
0.7228	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4360	Phase 2
0.7211	Intermediate Similarity	NPD4363	Phase 3
0.7202	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7286	Phase 2
0.7188	Intermediate Similarity	NPD7700	Phase 2
0.7188	Intermediate Similarity	NPD7699	Phase 2
0.7168	Intermediate Similarity	NPD7458	Discontinued
0.7168	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD8434	Phase 2
0.716	Intermediate Similarity	NPD2309	Approved
0.7157	Intermediate Similarity	NPD7584	Approved
0.7151	Intermediate Similarity	NPD8054	Approved
0.7151	Intermediate Similarity	NPD8053	Approved
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD1243	Approved
0.7136	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7874	Approved
0.7135	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7549	Discontinued
0.7134	Intermediate Similarity	NPD1610	Phase 2
0.7128	Intermediate Similarity	NPD6823	Phase 2
0.7126	Intermediate Similarity	NPD2346	Discontinued
0.712	Intermediate Similarity	NPD6535	Approved
0.712	Intermediate Similarity	NPD6534	Approved
0.7118	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6233	Phase 2
0.7108	Intermediate Similarity	NPD2799	Discontinued
0.7108	Intermediate Similarity	NPD7033	Discontinued
0.7101	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD8166	Discontinued
0.71	Intermediate Similarity	NPD7801	Approved
0.7092	Intermediate Similarity	NPD7680	Approved
0.7072	Intermediate Similarity	NPD5242	Approved
0.7066	Intermediate Similarity	NPD5406	Approved
0.7066	Intermediate Similarity	NPD5405	Approved
0.7066	Intermediate Similarity	NPD5408	Approved
0.7066	Intermediate Similarity	NPD5404	Approved
0.7063	Intermediate Similarity	NPD1203	Approved
0.7062	Intermediate Similarity	NPD5353	Approved
0.7056	Intermediate Similarity	NPD8319	Approved
0.7056	Intermediate Similarity	NPD8320	Phase 1
0.7055	Intermediate Similarity	NPD2313	Discontinued
0.7045	Intermediate Similarity	NPD6844	Discontinued
0.7033	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD5710	Approved
0.7017	Intermediate Similarity	NPD5711	Approved
0.7017	Intermediate Similarity	NPD7229	Phase 3
0.7	Intermediate Similarity	NPD4287	Approved
0.6989	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7039	Approved
0.6989	Remote Similarity	NPD7038	Approved
0.6987	Remote Similarity	NPD1548	Phase 1
0.6977	Remote Similarity	NPD7213	Phase 3
0.6977	Remote Similarity	NPD7212	Phase 2
0.6975	Remote Similarity	NPD3018	Phase 2
0.6975	Remote Similarity	NPD2861	Phase 2
0.6974	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7177	Discontinued
0.6951	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