NPASS Compound

Structure

CID266725 OpenBabel06191716072D 23 25 0 0 1 0 0 0 0 0999 V2000 -3.4641 -2.0000 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 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 0.3660 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -0.5000 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 -0.8660 -1.5000 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 -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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 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 1.3660 0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 22 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 12 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 9 18 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 15 1 0 0 0 0 11 17 2 0 0 0 0 12 18 1 0 0 0 0 13 14 1 0 0 0 0 13 19 2 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 15 20 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 21 1 1 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.12
Volume:	319.711
LogP:	2.829
LogD:	2.334
LogS:	-3.983
# Rotatable Bonds:	2
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.891
Synthetic Accessibility Score:	3.178
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.8
MDCK Permeability:	1.8329885278944857e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.605
Plasma Protein Binding (PPB):	94.54166412353516%
Volume Distribution (VD):	0.856
Pgp-substrate:	2.777406930923462%

ADMET: Metabolism

CYP1A2-inhibitor:	0.354
CYP1A2-substrate:	0.807
CYP2C19-inhibitor:	0.37
CYP2C19-substrate:	0.854
CYP2C9-inhibitor:	0.488
CYP2C9-substrate:	0.661
CYP2D6-inhibitor:	0.088
CYP2D6-substrate:	0.295
CYP3A4-inhibitor:	0.329
CYP3A4-substrate:	0.708

ADMET: Excretion

Clearance (CL):	12.259
Half-life (T1/2):	0.153

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.114
Drug-inuced Liver Injury (DILI):	0.792
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.612
Maximum Recommended Daily Dose:	0.335
Skin Sensitization:	0.867
Carcinogencity:	0.2
Eye Corrosion:	0.003
Eye Irritation:	0.465
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC266725

Natural Product ID:	NPC266725
*Common Name:**	(2S)-2,7-Dihydroxy-5-Methoxy-6,8-Dimethylflavanone
IUPAC Name:	(2S)-2,7-dihydroxy-5-methoxy-6,8-dimethyl-2-phenyl-3H-chromen-4-one
Synonyms:
Standard InCHIKey:	BIMVXOYXXZYVJF-SFHVURJKSA-N
Standard InCHI:	InChI=1S/C18H18O5/c1-10-15(20)11(2)17-14(16(10)22-3)13(19)9-18(21,23-17)12-7-5-4-6-8-12/h4-8,20-21H,9H2,1-3H3/t18-/m0/s1
SMILES:	Cc1c(c(C)c2c(C(=O)C[C@](c3ccccc3)(O)O2)c1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1271156
PubChem CID:	49831445
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002590] 5-O-methylated flavonoids

*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
NPO30425	Cleistocalyx operculatus	n.a.	n.a.	n.a.	n.a.	flower bud	n.a.	DOI[10.1021/np1002753]
NPO30425	Cleistocalyx operculatus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20886838]

☑ 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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	282580.0	nM	PMID[541424]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	284780.0	nM	PMID[541424]

☑ 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 NPC266725 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	351
0.1-0.2	1585
0.2-0.3	4157
0.3-0.4	10574
0.4-0.5	7689
0.5-0.6	3758
0.6-0.7	5882
0.7-0.8	5124
0.8-0.85	2081
0.85-0.9	1026
0.9-0.95	453
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9638	High Similarity	NPC110038
0.9638	High Similarity	NPC248372
0.9635	High Similarity	NPC217186
0.9635	High Similarity	NPC53181
0.9568	High Similarity	NPC167624
0.9568	High Similarity	NPC148757
0.9568	High Similarity	NPC37496
0.9568	High Similarity	NPC125855
0.9568	High Similarity	NPC296917
0.9568	High Similarity	NPC1089
0.9568	High Similarity	NPC194432
0.9568	High Similarity	NPC76338
0.9568	High Similarity	NPC306829
0.9568	High Similarity	NPC166934
0.9568	High Similarity	NPC182852
0.9568	High Similarity	NPC161506
0.9568	High Similarity	NPC177354
0.9568	High Similarity	NPC228504
0.9568	High Similarity	NPC32739
0.9568	High Similarity	NPC107572
0.9568	High Similarity	NPC227579
0.9568	High Similarity	NPC78
0.9568	High Similarity	NPC166482
0.9568	High Similarity	NPC223500
0.9568	High Similarity	NPC64915
0.9568	High Similarity	NPC265040
0.9568	High Similarity	NPC324436
0.9568	High Similarity	NPC220998
0.9568	High Similarity	NPC66515
0.9568	High Similarity	NPC324134
0.9568	High Similarity	NPC10937
0.9568	High Similarity	NPC328164
0.9568	High Similarity	NPC40833
0.9568	High Similarity	NPC76372
0.9565	High Similarity	NPC69769
0.9565	High Similarity	NPC241100
0.9565	High Similarity	NPC159275
0.95	High Similarity	NPC310130
0.95	High Similarity	NPC143896
0.95	High Similarity	NPC478086
0.95	High Similarity	NPC150408
0.95	High Similarity	NPC169591
0.95	High Similarity	NPC107177
0.95	High Similarity	NPC18585
0.95	High Similarity	NPC166138
0.95	High Similarity	NPC106985
0.95	High Similarity	NPC223812
0.95	High Similarity	NPC91560
0.95	High Similarity	NPC257097
0.95	High Similarity	NPC75049
0.95	High Similarity	NPC164980
0.95	High Similarity	NPC125894
0.95	High Similarity	NPC149026
0.95	High Similarity	NPC214166
0.95	High Similarity	NPC68104
0.95	High Similarity	NPC77794
0.95	High Similarity	NPC39329
0.95	High Similarity	NPC185276
0.95	High Similarity	NPC278249
0.95	High Similarity	NPC221432
0.95	High Similarity	NPC85162
0.95	High Similarity	NPC81697
0.95	High Similarity	NPC316816
0.95	High Similarity	NPC175504
0.9496	High Similarity	NPC156190
0.9496	High Similarity	NPC312391
0.9496	High Similarity	NPC213322
0.9496	High Similarity	NPC96408
0.9496	High Similarity	NPC279650
0.9496	High Similarity	NPC17170
0.9496	High Similarity	NPC166689
0.9496	High Similarity	NPC110969
0.9496	High Similarity	NPC3188
0.9496	High Similarity	NPC4743
0.9496	High Similarity	NPC258630
0.9496	High Similarity	NPC324386
0.9496	High Similarity	NPC282300
0.9493	High Similarity	NPC78913
0.9493	High Similarity	NPC220062
0.9493	High Similarity	NPC96565
0.9493	High Similarity	NPC216978
0.9493	High Similarity	NPC301217
0.9493	High Similarity	NPC303633
0.9493	High Similarity	NPC55018
0.9493	High Similarity	NPC18260
0.9444	High Similarity	NPC325429
0.9433	High Similarity	NPC235217
0.9433	High Similarity	NPC131568
0.9433	High Similarity	NPC271288
0.9433	High Similarity	NPC473013
0.9433	High Similarity	NPC209040
0.9433	High Similarity	NPC469953
0.9433	High Similarity	NPC131579
0.9433	High Similarity	NPC473015
0.9433	High Similarity	NPC473014
0.9433	High Similarity	NPC197252
0.9433	High Similarity	NPC236766
0.9429	High Similarity	NPC226636
0.9429	High Similarity	NPC11561
0.9429	High Similarity	NPC36181
0.9429	High Similarity	NPC144499
0.9424	High Similarity	NPC261227
0.9424	High Similarity	NPC270883
0.9424	High Similarity	NPC150522
0.9424	High Similarity	NPC6407
0.9424	High Similarity	NPC188243
0.9424	High Similarity	NPC172986
0.9424	High Similarity	NPC110228
0.9424	High Similarity	NPC76445
0.9424	High Similarity	NPC129853
0.9424	High Similarity	NPC284550
0.942	High Similarity	NPC201395
0.9412	High Similarity	NPC103842
0.9379	High Similarity	NPC166067
0.9366	High Similarity	NPC111786
0.9366	High Similarity	NPC195621
0.9366	High Similarity	NPC476153
0.9366	High Similarity	NPC215885
0.9366	High Similarity	NPC20488
0.9366	High Similarity	NPC246948
0.9366	High Similarity	NPC312973
0.9366	High Similarity	NPC470322
0.9366	High Similarity	NPC267375
0.9366	High Similarity	NPC228779
0.9366	High Similarity	NPC176229
0.9366	High Similarity	NPC214774
0.9366	High Similarity	NPC285630
0.9366	High Similarity	NPC127059
0.9366	High Similarity	NPC470131
0.9366	High Similarity	NPC88964
0.9366	High Similarity	NPC470134
0.9366	High Similarity	NPC470647
0.9366	High Similarity	NPC142405
0.9366	High Similarity	NPC301276
0.9366	High Similarity	NPC2416
0.9366	High Similarity	NPC477955
0.9366	High Similarity	NPC475052
0.9366	High Similarity	NPC54577
0.9366	High Similarity	NPC473078
0.9366	High Similarity	NPC470133
0.9366	High Similarity	NPC67805
0.9366	High Similarity	NPC83357
0.9366	High Similarity	NPC109183
0.9366	High Similarity	NPC470132
0.9366	High Similarity	NPC472629
0.9362	High Similarity	NPC188632
0.9362	High Similarity	NPC38219
0.9362	High Similarity	NPC112791
0.9362	High Similarity	NPC196459
0.9362	High Similarity	NPC471621
0.9362	High Similarity	NPC470296
0.9362	High Similarity	NPC219915
0.9362	High Similarity	NPC87609
0.9362	High Similarity	NPC94794
0.9357	High Similarity	NPC156590
0.9357	High Similarity	NPC147688
0.9357	High Similarity	NPC103362
0.9357	High Similarity	NPC205006
0.9357	High Similarity	NPC118840
0.9357	High Similarity	NPC64908
0.9353	High Similarity	NPC310135
0.9353	High Similarity	NPC274784
0.9353	High Similarity	NPC329203
0.9353	High Similarity	NPC20709
0.9353	High Similarity	NPC265871
0.9353	High Similarity	NPC140890
0.9353	High Similarity	NPC222342
0.9353	High Similarity	NPC150648
0.9353	High Similarity	NPC225153
0.9343	High Similarity	NPC13575
0.9343	High Similarity	NPC156092
0.9306	High Similarity	NPC104236
0.9306	High Similarity	NPC164205
0.9306	High Similarity	NPC19238
0.9301	High Similarity	NPC300988
0.9301	High Similarity	NPC140120
0.9301	High Similarity	NPC472627
0.9301	High Similarity	NPC283234
0.9301	High Similarity	NPC110303
0.9301	High Similarity	NPC296998
0.9301	High Similarity	NPC308200
0.9301	High Similarity	NPC23728
0.9301	High Similarity	NPC10990
0.9301	High Similarity	NPC473077
0.9296	High Similarity	NPC469935
0.9296	High Similarity	NPC178627
0.9296	High Similarity	NPC1886
0.9296	High Similarity	NPC470135
0.9296	High Similarity	NPC271590
0.9296	High Similarity	NPC87486
0.9296	High Similarity	NPC124780
0.9296	High Similarity	NPC234629
0.9296	High Similarity	NPC273538
0.9296	High Similarity	NPC39045
0.9296	High Similarity	NPC470136
0.9296	High Similarity	NPC216538
0.9296	High Similarity	NPC470890
0.9296	High Similarity	NPC311741
0.9296	High Similarity	NPC196137
0.9296	High Similarity	NPC319752

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 NPC266725 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	939
0.2-0.3	1528
0.3-0.4	2671
0.4-0.5	1902
0.5-0.6	1183
0.6-0.7	409
0.7-0.8	130
0.8-0.85	40
0.85-0.9	15
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9296	High Similarity	NPD4378	Clinical (unspecified phase)
0.9209	High Similarity	NPD1552	Clinical (unspecified phase)
0.9209	High Similarity	NPD1550	Clinical (unspecified phase)
0.9161	High Similarity	NPD7410	Clinical (unspecified phase)
0.9143	High Similarity	NPD1549	Phase 2
0.9048	High Similarity	NPD7411	Suspended
0.8926	High Similarity	NPD2393	Clinical (unspecified phase)
0.8913	High Similarity	NPD1240	Approved
0.8874	High Similarity	NPD7075	Discontinued
0.8867	High Similarity	NPD8443	Clinical (unspecified phase)
0.88	High Similarity	NPD7819	Suspended
0.88	High Similarity	NPD7096	Clinical (unspecified phase)
0.8794	High Similarity	NPD1510	Phase 2
0.8786	High Similarity	NPD1607	Approved
0.875	High Similarity	NPD4381	Clinical (unspecified phase)
0.8732	High Similarity	NPD2796	Approved
0.8725	High Similarity	NPD4380	Phase 2
0.8609	High Similarity	NPD1934	Approved
0.8609	High Similarity	NPD6801	Discontinued
0.8608	High Similarity	NPD7804	Clinical (unspecified phase)
0.8571	High Similarity	NPD6799	Approved
0.8552	High Similarity	NPD7421	Clinical (unspecified phase)
0.8535	High Similarity	NPD7852	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1511	Approved
0.8442	Intermediate Similarity	NPD7768	Phase 2
0.8431	Intermediate Similarity	NPD2801	Approved
0.8425	Intermediate Similarity	NPD2800	Approved
0.8392	Intermediate Similarity	NPD6651	Approved
0.8369	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD3750	Approved
0.8355	Intermediate Similarity	NPD6599	Discontinued
0.8344	Intermediate Similarity	NPD6959	Discontinued
0.8333	Intermediate Similarity	NPD1512	Approved
0.8323	Intermediate Similarity	NPD7074	Phase 3
0.8269	Intermediate Similarity	NPD3749	Approved
0.8261	Intermediate Similarity	NPD7054	Approved
0.8231	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD6559	Discontinued
0.8219	Intermediate Similarity	NPD2935	Discontinued
0.8219	Intermediate Similarity	NPD1551	Phase 2
0.821	Intermediate Similarity	NPD7472	Approved
0.8205	Intermediate Similarity	NPD3882	Suspended
0.8199	Intermediate Similarity	NPD3818	Discontinued
0.8187	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6166	Phase 2
0.8176	Intermediate Similarity	NPD1243	Approved
0.816	Intermediate Similarity	NPD6797	Phase 2
0.8151	Intermediate Similarity	NPD2799	Discontinued
0.8146	Intermediate Similarity	NPD2532	Approved
0.8146	Intermediate Similarity	NPD2534	Approved
0.8146	Intermediate Similarity	NPD2533	Approved
0.8141	Intermediate Similarity	NPD3817	Phase 2
0.8121	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD2313	Discontinued
0.811	Intermediate Similarity	NPD7251	Discontinued
0.8063	Intermediate Similarity	NPD6232	Discontinued
0.8061	Intermediate Similarity	NPD7808	Phase 3
0.805	Intermediate Similarity	NPD5494	Approved
0.8049	Intermediate Similarity	NPD5953	Discontinued
0.8039	Intermediate Similarity	NPD5403	Approved
0.8039	Intermediate Similarity	NPD920	Approved
0.8037	Intermediate Similarity	NPD7286	Phase 2
0.8027	Intermediate Similarity	NPD3748	Approved
0.8025	Intermediate Similarity	NPD7473	Discontinued
0.8014	Intermediate Similarity	NPD1203	Approved
0.8013	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD2798	Approved
0.7952	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD2346	Discontinued
0.7919	Intermediate Similarity	NPD2344	Approved
0.7908	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD5401	Approved
0.7862	Intermediate Similarity	NPD3268	Approved
0.7857	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD6099	Approved
0.7852	Intermediate Similarity	NPD6100	Approved
0.7847	Intermediate Similarity	NPD6832	Phase 2
0.7847	Intermediate Similarity	NPD4908	Phase 1
0.7823	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD5124	Phase 1
0.7823	Intermediate Similarity	NPD1933	Approved
0.7821	Intermediate Similarity	NPD3226	Approved
0.7818	Intermediate Similarity	NPD5844	Phase 1
0.7801	Intermediate Similarity	NPD9717	Approved
0.7785	Intermediate Similarity	NPD7033	Discontinued
0.7785	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD4628	Phase 3
0.7762	Intermediate Similarity	NPD2797	Approved
0.773	Intermediate Similarity	NPD1610	Phase 2
0.773	Intermediate Similarity	NPD422	Phase 1
0.7722	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2309	Approved
0.7698	Intermediate Similarity	NPD1548	Phase 1
0.7692	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5402	Approved
0.7654	Intermediate Similarity	NPD919	Approved
0.7635	Intermediate Similarity	NPD943	Approved
0.7622	Intermediate Similarity	NPD5710	Approved
0.7622	Intermediate Similarity	NPD5711	Approved
0.7613	Intermediate Similarity	NPD7390	Discontinued
0.76	Intermediate Similarity	NPD4363	Phase 3
0.76	Intermediate Similarity	NPD4360	Phase 2
0.7595	Intermediate Similarity	NPD7458	Discontinued
0.7582	Intermediate Similarity	NPD2654	Approved
0.7569	Intermediate Similarity	NPD3225	Approved
0.7551	Intermediate Similarity	NPD4625	Phase 3
0.755	Intermediate Similarity	NPD4308	Phase 3
0.7517	Intermediate Similarity	NPD3267	Approved
0.7517	Intermediate Similarity	NPD3266	Approved
0.7516	Intermediate Similarity	NPD1465	Phase 2
0.7515	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5890	Approved
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5889	Approved
0.7486	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3926	Phase 2
0.7458	Intermediate Similarity	NPD4361	Phase 2
0.7458	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD1729	Discontinued
0.7455	Intermediate Similarity	NPD1247	Approved
0.7452	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD9545	Approved
0.7438	Intermediate Similarity	NPD6585	Discontinued
0.7432	Intermediate Similarity	NPD7584	Approved
0.7431	Intermediate Similarity	NPD1608	Approved
0.7431	Intermediate Similarity	NPD3972	Approved
0.7429	Intermediate Similarity	NPD9493	Approved
0.7386	Intermediate Similarity	NPD5406	Approved
0.7386	Intermediate Similarity	NPD5405	Approved
0.7386	Intermediate Similarity	NPD5404	Approved
0.7386	Intermediate Similarity	NPD5408	Approved
0.7384	Intermediate Similarity	NPD8313	Approved
0.7384	Intermediate Similarity	NPD8312	Approved
0.7383	Intermediate Similarity	NPD6798	Discontinued
0.7383	Intermediate Similarity	NPD1296	Phase 2
0.7375	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD4287	Approved
0.7365	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD4288	Approved
0.7351	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7199	Phase 2
0.7338	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3751	Discontinued
0.7308	Intermediate Similarity	NPD7003	Approved
0.7305	Intermediate Similarity	NPD7229	Phase 3
0.7305	Intermediate Similarity	NPD3787	Discontinued
0.7301	Intermediate Similarity	NPD8455	Phase 2
0.7297	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5049	Phase 3
0.7293	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1613	Approved
0.7285	Intermediate Similarity	NPD4307	Phase 2
0.7285	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1164	Approved
0.7267	Intermediate Similarity	NPD6104	Discontinued
0.7267	Intermediate Similarity	NPD411	Approved
0.7267	Intermediate Similarity	NPD3764	Approved
0.7262	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4749	Approved
0.7241	Intermediate Similarity	NPD1201	Approved
0.7237	Intermediate Similarity	NPD230	Phase 1
0.7237	Intermediate Similarity	NPD447	Suspended
0.723	Intermediate Similarity	NPD1019	Discontinued
0.7222	Intermediate Similarity	NPD17	Approved
0.7214	Intermediate Similarity	NPD1241	Discontinued
0.7203	Intermediate Similarity	NPD1894	Discontinued
0.7198	Intermediate Similarity	NPD6778	Approved
0.7198	Intermediate Similarity	NPD6779	Approved
0.7198	Intermediate Similarity	NPD6776	Approved
0.7198	Intermediate Similarity	NPD6777	Approved
0.7198	Intermediate Similarity	NPD6782	Approved
0.7198	Intermediate Similarity	NPD6780	Approved
0.7198	Intermediate Similarity	NPD6781	Approved
0.7192	Intermediate Similarity	NPD1481	Phase 2
0.7175	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1470	Approved
0.7161	Intermediate Similarity	NPD4477	Approved
0.7161	Intermediate Similarity	NPD4476	Approved
0.7153	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2354	Approved
0.7152	Intermediate Similarity	NPD2296	Approved
0.7135	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1652	Phase 2
0.7134	Intermediate Similarity	NPD37	Approved
0.7126	Intermediate Similarity	NPD6234	Discontinued
0.7124	Intermediate Similarity	NPD6355	Discontinued
0.7123	Intermediate Similarity	NPD1535	Discovery
0.7118	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6002	Phase 3
0.7115	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6004	Phase 3
0.7115	Intermediate Similarity	NPD6005	Phase 3

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