NPASS Compound

Structure

CID245482 OpenBabel06191716042D 26 27 0 0 1 0 0 0 0 0999 V2000 0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 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 -0.8660 3.5000 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 0.0000 3.0000 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 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 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 0.0000 2.0000 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 2.5981 0.5000 0.0000 C 0 0 1 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 1.7321 -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 -1.7321 2.0000 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 1.7321 -1.0000 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 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 26 1 0 0 0 0 4 7 1 0 0 0 0 4 13 2 0 0 0 0 5 8 1 0 0 0 0 5 14 2 0 0 0 0 6 9 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 19 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 12 20 1 0 0 0 0 15 18 1 0 0 0 0 16 22 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 18 23 1 0 0 0 0 19 21 1 0 0 0 0 19 24 1 6 0 0 0 20 26 1 0 0 0 0 21 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.16
Volume:	377.519
LogP:	3.569
LogD:	3.06
LogS:	-3.698
# Rotatable Bonds:	7
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.523
Synthetic Accessibility Score:	3.046
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.718
MDCK Permeability:	1.4898758308845572e-05
Pgp-inhibitor:	0.048
Pgp-substrate:	0.083
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.937
30% Bioavailability (F30%):	0.84

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	97.92852020263672%
Volume Distribution (VD):	0.601
Pgp-substrate:	1.4618616104125977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.749
CYP1A2-substrate:	0.831
CYP2C19-inhibitor:	0.706
CYP2C19-substrate:	0.187
CYP2C9-inhibitor:	0.713
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.88
CYP2D6-substrate:	0.845
CYP3A4-inhibitor:	0.429
CYP3A4-substrate:	0.338

ADMET: Excretion

Clearance (CL):	14.225
Half-life (T1/2):	0.78

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.242
Drug-inuced Liver Injury (DILI):	0.278
AMES Toxicity:	0.093
Rat Oral Acute Toxicity:	0.12
Maximum Recommended Daily Dose:	0.301
Skin Sensitization:	0.518
Carcinogencity:	0.09
Eye Corrosion:	0.003
Eye Irritation:	0.215
Respiratory Toxicity:	0.086

Download Data

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

Natural Product: NPC245482

Natural Product ID:	NPC245482
*Common Name:**	Lespeflorin C3
IUPAC Name:	(2S)-2-hydroxy-1-[4-hydroxy-2-methoxy-5-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)propan-1-one
Synonyms:	Lespeflorin C3
Standard InCHIKey:	XTDORSAGLFPXGX-IBGZPJMESA-N
Standard InCHI:	InChI=1S/C21H24O5/c1-13(2)4-7-15-11-17(20(26-3)12-18(15)23)21(25)19(24)10-14-5-8-16(22)9-6-14/h4-6,8-9,11-12,19,22-24H,7,10H2,1-3H3/t19-/m0/s1
SMILES:	COc1cc(O)c(cc1C(=O)[C@H](Cc1ccc(cc1)O)O)CC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL560625
PubChem CID:	25243322
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0003496] Cinnamylphenols

*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
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	1680.0	nM	PMID[564722]

☑ 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 NPC245482 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	357
0.1-0.2	1405
0.2-0.3	3640
0.3-0.4	8974
0.4-0.5	9561
0.5-0.6	3618
0.6-0.7	5708
0.7-0.8	5652
0.8-0.85	2330
0.85-0.9	1012
0.9-0.95	423
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC301751
0.9927	High Similarity	NPC148545
0.9854	High Similarity	NPC321980
0.9854	High Similarity	NPC470087
0.9712	High Similarity	NPC51887
0.9712	High Similarity	NPC475705
0.9712	High Similarity	NPC117836
0.9712	High Similarity	NPC476178
0.971	High Similarity	NPC470089
0.9708	High Similarity	NPC470211
0.958	High Similarity	NPC61258
0.9574	High Similarity	NPC316769
0.9568	High Similarity	NPC469404
0.9507	High Similarity	NPC222298
0.9507	High Similarity	NPC51070
0.9504	High Similarity	NPC328623
0.9496	High Similarity	NPC215311
0.9496	High Similarity	NPC213659
0.9496	High Similarity	NPC172250
0.9496	High Similarity	NPC326109
0.9496	High Similarity	NPC48624
0.9496	High Similarity	NPC204985
0.9496	High Similarity	NPC259166
0.9496	High Similarity	NPC144118
0.9496	High Similarity	NPC80962
0.9496	High Similarity	NPC219917
0.9493	High Similarity	NPC21350
0.9489	High Similarity	NPC477244
0.9489	High Similarity	NPC274109
0.9489	High Similarity	NPC150399
0.9489	High Similarity	NPC98115
0.9489	High Similarity	NPC477243
0.9489	High Similarity	NPC477242
0.9489	High Similarity	NPC249606
0.9489	High Similarity	NPC1486
0.9489	High Similarity	NPC12165
0.9489	High Similarity	NPC186838
0.9489	High Similarity	NPC168105
0.9489	High Similarity	NPC66349
0.9489	High Similarity	NPC41461
0.9489	High Similarity	NPC25287
0.9448	High Similarity	NPC171651
0.9448	High Similarity	NPC35567
0.9448	High Similarity	NPC243171
0.9437	High Similarity	NPC472629
0.9429	High Similarity	NPC55832
0.9429	High Similarity	NPC268204
0.9429	High Similarity	NPC52789
0.9429	High Similarity	NPC26051
0.9424	High Similarity	NPC283429
0.9424	High Similarity	NPC477956
0.9424	High Similarity	NPC295384
0.942	High Similarity	NPC317119
0.942	High Similarity	NPC472419
0.942	High Similarity	NPC153979
0.9416	High Similarity	NPC156092
0.9416	High Similarity	NPC131039
0.9416	High Similarity	NPC84699
0.9416	High Similarity	NPC13575
0.9384	High Similarity	NPC293286
0.9379	High Similarity	NPC262038
0.9379	High Similarity	NPC278476
0.9379	High Similarity	NPC262039
0.9379	High Similarity	NPC319910
0.9379	High Similarity	NPC254412
0.9375	High Similarity	NPC89442
0.9375	High Similarity	NPC470461
0.9366	High Similarity	NPC216538
0.9366	High Similarity	NPC470890
0.9366	High Similarity	NPC87486
0.9366	High Similarity	NPC273538
0.9366	High Similarity	NPC224714
0.9366	High Similarity	NPC124780
0.9357	High Similarity	NPC253822
0.9357	High Similarity	NPC101366
0.9357	High Similarity	NPC11056
0.9353	High Similarity	NPC471620
0.9343	High Similarity	NPC283590
0.9343	High Similarity	NPC286336
0.9343	High Similarity	NPC130899
0.9343	High Similarity	NPC61153
0.9343	High Similarity	NPC70859
0.9343	High Similarity	NPC164136
0.9343	High Similarity	NPC103842
0.9315	High Similarity	NPC138288
0.9315	High Similarity	NPC217149
0.9315	High Similarity	NPC216035
0.931	High Similarity	NPC105136
0.9306	High Similarity	NPC168085
0.9306	High Similarity	NPC470460
0.9301	High Similarity	NPC5820
0.9301	High Similarity	NPC124729
0.9301	High Similarity	NPC470458
0.9301	High Similarity	NPC178343
0.9301	High Similarity	NPC306488
0.9296	High Similarity	NPC143896
0.9296	High Similarity	NPC169591
0.9296	High Similarity	NPC190637
0.9296	High Similarity	NPC310130
0.9296	High Similarity	NPC150408
0.9296	High Similarity	NPC9117
0.9296	High Similarity	NPC221432
0.9296	High Similarity	NPC212932
0.9296	High Similarity	NPC68104
0.9296	High Similarity	NPC91560
0.9296	High Similarity	NPC75049
0.9296	High Similarity	NPC293053
0.9296	High Similarity	NPC164980
0.9296	High Similarity	NPC149026
0.9296	High Similarity	NPC24821
0.9296	High Similarity	NPC257097
0.9296	High Similarity	NPC39329
0.9296	High Similarity	NPC175504
0.9286	High Similarity	NPC472366
0.9281	High Similarity	NPC116632
0.9281	High Similarity	NPC181124
0.9281	High Similarity	NPC303644
0.9281	High Similarity	NPC209560
0.9281	High Similarity	NPC294409
0.9281	High Similarity	NPC162680
0.9281	High Similarity	NPC7013
0.927	High Similarity	NPC242294
0.927	High Similarity	NPC144051
0.927	High Similarity	NPC175098
0.927	High Similarity	NPC204960
0.927	High Similarity	NPC139813
0.927	High Similarity	NPC337373
0.927	High Similarity	NPC192304
0.927	High Similarity	NPC294593
0.927	High Similarity	NPC27643
0.927	High Similarity	NPC18877
0.927	High Similarity	NPC82225
0.927	High Similarity	NPC20560
0.927	High Similarity	NPC188646
0.927	High Similarity	NPC56031
0.927	High Similarity	NPC312318
0.927	High Similarity	NPC472365
0.927	High Similarity	NPC263670
0.927	High Similarity	NPC159623
0.927	High Similarity	NPC28753
0.9252	High Similarity	NPC193200
0.9247	High Similarity	NPC474772
0.9247	High Similarity	NPC474744
0.9247	High Similarity	NPC472420
0.9247	High Similarity	NPC472422
0.9247	High Similarity	NPC471676
0.9247	High Similarity	NPC263384
0.9247	High Similarity	NPC244577
0.9247	High Similarity	NPC472423
0.9241	High Similarity	NPC5173
0.9241	High Similarity	NPC317492
0.9231	High Similarity	NPC473013
0.9231	High Similarity	NPC236766
0.9231	High Similarity	NPC473015
0.9231	High Similarity	NPC326500
0.9231	High Similarity	NPC476055
0.9231	High Similarity	NPC197252
0.9231	High Similarity	NPC209040
0.9225	High Similarity	NPC194432
0.9225	High Similarity	NPC125855
0.9225	High Similarity	NPC296917
0.9225	High Similarity	NPC200694
0.9225	High Similarity	NPC76372
0.9225	High Similarity	NPC66515
0.9225	High Similarity	NPC228504
0.9225	High Similarity	NPC148757
0.9225	High Similarity	NPC78
0.9225	High Similarity	NPC166482
0.9225	High Similarity	NPC10937
0.9225	High Similarity	NPC220998
0.9225	High Similarity	NPC182852
0.9225	High Similarity	NPC161506
0.9225	High Similarity	NPC64915
0.9225	High Similarity	NPC162476
0.9225	High Similarity	NPC107572
0.9225	High Similarity	NPC227579
0.9225	High Similarity	NPC166934
0.9225	High Similarity	NPC167624
0.9225	High Similarity	NPC223500
0.9225	High Similarity	NPC324134
0.9225	High Similarity	NPC1089
0.9225	High Similarity	NPC473042
0.9225	High Similarity	NPC177354
0.9225	High Similarity	NPC37496
0.9225	High Similarity	NPC32739
0.9225	High Similarity	NPC40833
0.9225	High Similarity	NPC324436
0.9225	High Similarity	NPC328164
0.9225	High Similarity	NPC265040
0.9225	High Similarity	NPC76338
0.9225	High Similarity	NPC306829
0.9214	High Similarity	NPC55162
0.9214	High Similarity	NPC279668
0.9214	High Similarity	NPC309154
0.9214	High Similarity	NPC124269
0.9214	High Similarity	NPC90665
0.9214	High Similarity	NPC251681
0.9214	High Similarity	NPC12175
0.9214	High Similarity	NPC278323
0.9214	High Similarity	NPC243528

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 NPC245482 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	903
0.2-0.3	1557
0.3-0.4	2571
0.4-0.5	1966
0.5-0.6	1155
0.6-0.7	467
0.7-0.8	163
0.8-0.85	35
0.85-0.9	15
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9366	High Similarity	NPD4378	Clinical (unspecified phase)
0.9178	High Similarity	NPD4380	Phase 2
0.9137	High Similarity	NPD1510	Phase 2
0.9124	High Similarity	NPD1240	Approved
0.8993	High Similarity	NPD1607	Approved
0.8944	High Similarity	NPD1549	Phase 2
0.894	High Similarity	NPD7075	Discontinued
0.8873	High Similarity	NPD1550	Clinical (unspecified phase)
0.8873	High Similarity	NPD1552	Clinical (unspecified phase)
0.8867	High Similarity	NPD7096	Clinical (unspecified phase)
0.8867	High Similarity	NPD2393	Clinical (unspecified phase)
0.8803	High Similarity	NPD2796	Approved
0.88	High Similarity	NPD6801	Discontinued
0.8707	High Similarity	NPD7410	Clinical (unspecified phase)
0.8684	High Similarity	NPD8443	Clinical (unspecified phase)
0.8639	High Similarity	NPD6799	Approved
0.8609	High Similarity	NPD7411	Suspended
0.8571	High Similarity	NPD4381	Clinical (unspecified phase)
0.8553	High Similarity	NPD1934	Approved
0.8553	High Similarity	NPD7804	Clinical (unspecified phase)
0.8542	High Similarity	NPD2935	Discontinued
0.8506	High Similarity	NPD3882	Suspended
0.8497	Intermediate Similarity	NPD7819	Suspended
0.8481	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD6166	Phase 2
0.8481	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD6599	Discontinued
0.84	Intermediate Similarity	NPD1512	Approved
0.8333	Intermediate Similarity	NPD6651	Approved
0.8311	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD6959	Discontinued
0.8269	Intermediate Similarity	NPD7768	Phase 2
0.8267	Intermediate Similarity	NPD1511	Approved
0.8258	Intermediate Similarity	NPD2801	Approved
0.825	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD2800	Approved
0.8224	Intermediate Similarity	NPD5403	Approved
0.8212	Intermediate Similarity	NPD2533	Approved
0.8212	Intermediate Similarity	NPD2534	Approved
0.8212	Intermediate Similarity	NPD2532	Approved
0.8205	Intermediate Similarity	NPD3817	Phase 2
0.8176	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1551	Phase 2
0.8148	Intermediate Similarity	NPD3818	Discontinued
0.8125	Intermediate Similarity	NPD6232	Discontinued
0.8113	Intermediate Similarity	NPD5494	Approved
0.811	Intermediate Similarity	NPD6797	Phase 2
0.8105	Intermediate Similarity	NPD920	Approved
0.8092	Intermediate Similarity	NPD5401	Approved
0.8089	Intermediate Similarity	NPD5402	Approved
0.8086	Intermediate Similarity	NPD7473	Discontinued
0.8067	Intermediate Similarity	NPD3750	Approved
0.8061	Intermediate Similarity	NPD7251	Discontinued
0.8061	Intermediate Similarity	NPD6559	Discontinued
0.8056	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7074	Phase 3
0.8012	Intermediate Similarity	NPD7808	Phase 3
0.8	Intermediate Similarity	NPD5953	Discontinued
0.8	Intermediate Similarity	NPD1243	Approved
0.7988	Intermediate Similarity	NPD7286	Phase 2
0.7988	Intermediate Similarity	NPD7054	Approved
0.7974	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD2799	Discontinued
0.7973	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD4628	Phase 3
0.7945	Intermediate Similarity	NPD943	Approved
0.7939	Intermediate Similarity	NPD7472	Approved
0.7925	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD5844	Phase 1
0.7875	Intermediate Similarity	NPD3749	Approved
0.7867	Intermediate Similarity	NPD2344	Approved
0.784	Intermediate Similarity	NPD1247	Approved
0.7826	Intermediate Similarity	NPD919	Approved
0.7808	Intermediate Similarity	NPD2313	Discontinued
0.7792	Intermediate Similarity	NPD7390	Discontinued
0.7784	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2798	Approved
0.7746	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD3748	Approved
0.7708	Intermediate Similarity	NPD1203	Approved
0.7687	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD6832	Phase 2
0.767	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2309	Approved
0.7658	Intermediate Similarity	NPD3226	Approved
0.7657	Intermediate Similarity	NPD4360	Phase 2
0.7657	Intermediate Similarity	NPD4363	Phase 3
0.7647	Intermediate Similarity	NPD2654	Approved
0.7636	Intermediate Similarity	NPD3926	Phase 2
0.7622	Intermediate Similarity	NPD3972	Approved
0.7619	Intermediate Similarity	NPD3027	Phase 3
0.7616	Intermediate Similarity	NPD7033	Discontinued
0.7616	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5710	Approved
0.7576	Intermediate Similarity	NPD5711	Approved
0.7551	Intermediate Similarity	NPD4908	Phase 1
0.7547	Intermediate Similarity	NPD7458	Discontinued
0.7533	Intermediate Similarity	NPD230	Phase 1
0.7532	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD9545	Approved
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD9493	Approved
0.7466	Intermediate Similarity	NPD1164	Approved
0.7453	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6100	Approved
0.7451	Intermediate Similarity	NPD6099	Approved
0.7444	Intermediate Similarity	NPD6777	Approved
0.7444	Intermediate Similarity	NPD6780	Approved
0.7444	Intermediate Similarity	NPD6778	Approved
0.7444	Intermediate Similarity	NPD6782	Approved
0.7444	Intermediate Similarity	NPD6781	Approved
0.7444	Intermediate Similarity	NPD6776	Approved
0.7444	Intermediate Similarity	NPD6779	Approved
0.7431	Intermediate Similarity	NPD1610	Phase 2
0.7417	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD5124	Phase 1
0.7416	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4361	Phase 2
0.7412	Intermediate Similarity	NPD1729	Discontinued
0.7396	Intermediate Similarity	NPD3751	Discontinued
0.7394	Intermediate Similarity	NPD1548	Phase 1
0.7372	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD7003	Approved
0.7351	Intermediate Similarity	NPD1613	Approved
0.7351	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1470	Approved
0.7338	Intermediate Similarity	NPD5405	Approved
0.7338	Intermediate Similarity	NPD5406	Approved
0.7338	Intermediate Similarity	NPD5408	Approved
0.7338	Intermediate Similarity	NPD5404	Approved
0.7333	Intermediate Similarity	NPD3268	Approved
0.7333	Intermediate Similarity	NPD6798	Discontinued
0.7329	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6190	Approved
0.7322	Intermediate Similarity	NPD7698	Approved
0.7322	Intermediate Similarity	NPD7696	Phase 3
0.7322	Intermediate Similarity	NPD7435	Discontinued
0.7322	Intermediate Similarity	NPD7697	Approved
0.7314	Intermediate Similarity	NPD8434	Phase 2
0.7314	Intermediate Similarity	NPD8150	Discontinued
0.731	Intermediate Similarity	NPD422	Phase 1
0.731	Intermediate Similarity	NPD1201	Approved
0.7303	Intermediate Similarity	NPD6355	Discontinued
0.7301	Intermediate Similarity	NPD37	Approved
0.7297	Intermediate Similarity	NPD7584	Approved
0.7296	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1471	Phase 3
0.729	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7870	Phase 2
0.7283	Intermediate Similarity	NPD7871	Phase 2
0.7279	Intermediate Similarity	NPD1876	Approved
0.7273	Intermediate Similarity	NPD4308	Phase 3
0.7262	Intermediate Similarity	NPD3787	Discontinued
0.7256	Intermediate Similarity	NPD1465	Phase 2
0.7244	Intermediate Similarity	NPD2424	Discontinued
0.7241	Intermediate Similarity	NPD8312	Approved
0.7241	Intermediate Similarity	NPD8313	Approved
0.7232	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD2797	Approved
0.7222	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3764	Approved
0.7215	Intermediate Similarity	NPD3887	Approved
0.7195	Intermediate Similarity	NPD6844	Discontinued
0.7193	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD447	Suspended
0.7188	Intermediate Similarity	NPD4661	Approved
0.7188	Intermediate Similarity	NPD4662	Approved
0.7181	Intermediate Similarity	NPD1019	Discontinued
0.7179	Intermediate Similarity	NPD6005	Phase 3
0.7179	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6004	Phase 3
0.7179	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6002	Phase 3
0.7176	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2403	Approved
0.7171	Intermediate Similarity	NPD6233	Phase 2
0.7169	Intermediate Similarity	NPD4965	Approved
0.7169	Intermediate Similarity	NPD4967	Phase 2
0.7169	Intermediate Similarity	NPD4966	Approved
0.7167	Intermediate Similarity	NPD6535	Approved
0.7167	Intermediate Similarity	NPD6534	Approved
0.7166	Intermediate Similarity	NPD7701	Phase 2
0.7163	Intermediate Similarity	NPD1241	Discontinued
0.716	Intermediate Similarity	NPD7229	Phase 3
0.7159	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4625	Phase 3
0.7152	Intermediate Similarity	NPD5760	Phase 2
0.7152	Intermediate Similarity	NPD5761	Phase 2
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD5049	Phase 3
0.7133	Intermediate Similarity	NPD9494	Approved
0.7128	Intermediate Similarity	NPD8151	Discontinued

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