NPASS Compound

Structure

NPC261471 OpenBabel07101718192D 27 30 0 0 0 0 0 0 0 0999 V2000 7.4300 1.8044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0288 2.8225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8477 1.1000 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 4.8532 1.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 3.0898 -1.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4355 1.9090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 4.2654 0.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0844 -1.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 4.6722 -0.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4911 -2.2406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6667 -0.6226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 2.6831 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 25 1 0 0 0 0 4 6 1 0 0 0 0 4 10 2 0 0 0 0 5 7 2 0 0 0 0 5 11 1 0 0 0 0 6 13 1 0 0 0 0 7 12 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 9 15 2 0 0 0 0 11 25 1 0 0 0 0 12 16 2 0 0 0 0 12 20 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 14 19 2 0 0 0 0 15 18 1 0 0 0 0 15 22 1 0 0 0 0 16 26 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 27 1 0 0 0 0 20 27 1 0 0 0 0 21 24 2 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.11
Volume:	366.56
LogP:	5.092
LogD:	3.323
LogS:	-4.237
# Rotatable Bonds:	3
TPSA:	93.04
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.312
Synthetic Accessibility Score:	2.862
Fsp3:	0.19
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.987
MDCK Permeability:	1.4773979273741134e-05
Pgp-inhibitor:	0.262
Pgp-substrate:	0.223
Human Intestinal Absorption (HIA):	0.088
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	79.96098327636719%
Volume Distribution (VD):	0.758
Pgp-substrate:	21.401098251342773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.95
CYP1A2-substrate:	0.663
CYP2C19-inhibitor:	0.788
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.782
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.27
CYP2D6-substrate:	0.571
CYP3A4-inhibitor:	0.22
CYP3A4-substrate:	0.076

ADMET: Excretion

Clearance (CL):	9.031
Half-life (T1/2):	0.334

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.985
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.22
Rat Oral Acute Toxicity:	0.522
Maximum Recommended Daily Dose:	0.84
Skin Sensitization:	0.817
Carcinogencity:	0.306
Eye Corrosion:	0.003
Eye Irritation:	0.099
Respiratory Toxicity:	0.36

Download Data

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

Natural Product: NPC261471

Natural Product ID:	NPC261471
*Common Name:**	Lespeflorin I3
IUPAC Name:	8,9-dihydroxy-3-methoxy-10-(3-methylbut-2-enyl)-[1]benzofuro[3,2-c]chromen-6-one
Synonyms:	Lespeflorin I3
Standard InCHIKey:	OCSVLSKWXCFMKU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H18O6/c1-10(2)4-6-13-18(23)15(22)9-14-17-20(27-19(13)14)12-7-5-11(25-3)8-16(12)26-21(17)24/h4-5,7-9,22-23H,6H2,1-3H3
SMILES:	COc1ccc2c(c1)oc(=O)c1c2oc2c1cc(c(c2CC=C(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL561441
PubChem CID:	25243076
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0000354] Coumestans

*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	=	27300.0	nM	PMID[557379]

☑ 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 NPC261471 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	400
0.1-0.2	1953
0.2-0.3	4349
0.3-0.4	10415
0.4-0.5	7698
0.5-0.6	3955
0.6-0.7	5455
0.7-0.8	4917
0.8-0.85	2171
0.85-0.9	1242
0.9-0.95	133
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9876	High Similarity	NPC218533
0.9876	High Similarity	NPC78830
0.9756	High Similarity	NPC164384
0.9755	High Similarity	NPC37606
0.9752	High Similarity	NPC86477
0.9581	High Similarity	NPC97523
0.9568	High Similarity	NPC277480
0.9509	High Similarity	NPC50394
0.9506	High Similarity	NPC37183
0.9506	High Similarity	NPC29411
0.9379	High Similarity	NPC115432
0.9379	High Similarity	NPC260296
0.9317	High Similarity	NPC244750
0.9281	High Similarity	NPC310794
0.9273	High Similarity	NPC247973
0.9268	High Similarity	NPC291110
0.9264	High Similarity	NPC84515
0.9264	High Similarity	NPC312056
0.9207	High Similarity	NPC155640
0.9202	High Similarity	NPC188486
0.9162	High Similarity	NPC120220
0.9162	High Similarity	NPC131866
0.9141	High Similarity	NPC300680
0.913	High Similarity	NPC113906
0.9118	High Similarity	NPC297807
0.9107	High Similarity	NPC248593
0.9107	High Similarity	NPC472584
0.9107	High Similarity	NPC28589
0.9091	High Similarity	NPC329669
0.9091	High Similarity	NPC133065
0.9091	High Similarity	NPC472278
0.9091	High Similarity	NPC89131
0.9091	High Similarity	NPC473313
0.9085	High Similarity	NPC472275
0.908	High Similarity	NPC16935
0.908	High Similarity	NPC185258
0.908	High Similarity	NPC172770
0.908	High Similarity	NPC196879
0.9064	High Similarity	NPC183843
0.9059	High Similarity	NPC8127
0.9059	High Similarity	NPC49667
0.9053	High Similarity	NPC473834
0.9053	High Similarity	NPC233956
0.9036	High Similarity	NPC45449
0.9036	High Similarity	NPC36320
0.9036	High Similarity	NPC39306
0.9023	High Similarity	NPC73929
0.9023	High Similarity	NPC47905
0.9023	High Similarity	NPC139683
0.9018	High Similarity	NPC262286
0.9018	High Similarity	NPC78225
0.9018	High Similarity	NPC79053
0.9018	High Similarity	NPC36852
0.9006	High Similarity	NPC98546
0.9006	High Similarity	NPC41326
0.9006	High Similarity	NPC125300
0.8994	High Similarity	NPC174700
0.8994	High Similarity	NPC158226
0.8988	High Similarity	NPC163130
0.8988	High Similarity	NPC202470
0.8988	High Similarity	NPC165979
0.8976	High Similarity	NPC1755
0.8976	High Similarity	NPC263092
0.8976	High Similarity	NPC39305
0.8976	High Similarity	NPC59295
0.8976	High Similarity	NPC474350
0.8976	High Similarity	NPC1706
0.897	High Similarity	NPC32694
0.8966	High Similarity	NPC304322
0.8957	High Similarity	NPC68093
0.8957	High Similarity	NPC142339
0.8957	High Similarity	NPC45131
0.8957	High Similarity	NPC191146
0.8957	High Similarity	NPC138243
0.8951	High Similarity	NPC213608
0.8951	High Similarity	NPC1477
0.8944	High Similarity	NPC170169
0.8941	High Similarity	NPC65885
0.8941	High Similarity	NPC82217
0.8941	High Similarity	NPC216842
0.8941	High Similarity	NPC476640
0.8935	High Similarity	NPC281835
0.8929	High Similarity	NPC234331
0.8929	High Similarity	NPC320789
0.8922	High Similarity	NPC204088
0.8922	High Similarity	NPC473286
0.8922	High Similarity	NPC38914
0.8922	High Similarity	NPC326520
0.8922	High Similarity	NPC259007
0.8922	High Similarity	NPC329215
0.8922	High Similarity	NPC472277
0.892	High Similarity	NPC295436
0.8916	High Similarity	NPC83922
0.8916	High Similarity	NPC81679
0.8916	High Similarity	NPC238995
0.8916	High Similarity	NPC272722
0.8916	High Similarity	NPC472448
0.8916	High Similarity	NPC329760
0.8909	High Similarity	NPC45146
0.8909	High Similarity	NPC235018
0.8909	High Similarity	NPC228785
0.8909	High Similarity	NPC56085
0.8909	High Similarity	NPC476980
0.8909	High Similarity	NPC14353
0.8902	High Similarity	NPC236796
0.8902	High Similarity	NPC47883
0.8896	High Similarity	NPC152951
0.8896	High Similarity	NPC117992
0.8896	High Similarity	NPC148938
0.8896	High Similarity	NPC230149
0.8896	High Similarity	NPC168247
0.8896	High Similarity	NPC57674
0.8889	High Similarity	NPC5871
0.8889	High Similarity	NPC227906
0.8889	High Similarity	NPC287243
0.8882	High Similarity	NPC81332
0.8882	High Similarity	NPC262580
0.8882	High Similarity	NPC78335
0.8882	High Similarity	NPC289396
0.8882	High Similarity	NPC307286
0.8882	High Similarity	NPC247964
0.8882	High Similarity	NPC271848
0.8882	High Similarity	NPC230713
0.8882	High Similarity	NPC230619
0.8882	High Similarity	NPC212038
0.8882	High Similarity	NPC62042
0.8882	High Similarity	NPC54098
0.8876	High Similarity	NPC99613
0.8876	High Similarity	NPC49487
0.8876	High Similarity	NPC211309
0.8869	High Similarity	NPC323137
0.8869	High Similarity	NPC170245
0.8869	High Similarity	NPC472452
0.8869	High Similarity	NPC235610
0.8869	High Similarity	NPC29160
0.8862	High Similarity	NPC205265
0.8862	High Similarity	NPC124038
0.8862	High Similarity	NPC472281
0.8862	High Similarity	NPC220313
0.8862	High Similarity	NPC18100
0.8862	High Similarity	NPC234004
0.8855	High Similarity	NPC61010
0.8855	High Similarity	NPC45124
0.8855	High Similarity	NPC278052
0.8855	High Similarity	NPC258331
0.8855	High Similarity	NPC40491
0.8855	High Similarity	NPC29876
0.8855	High Similarity	NPC167678
0.8855	High Similarity	NPC266314
0.8855	High Similarity	NPC30655
0.8855	High Similarity	NPC74854
0.8848	High Similarity	NPC95936
0.8848	High Similarity	NPC168616
0.8848	High Similarity	NPC100123
0.8848	High Similarity	NPC250214
0.8848	High Similarity	NPC83763
0.8841	High Similarity	NPC160015
0.8841	High Similarity	NPC472916
0.8841	High Similarity	NPC247677
0.8841	High Similarity	NPC13879
0.8837	High Similarity	NPC107244
0.8837	High Similarity	NPC24258
0.8834	High Similarity	NPC167091
0.8834	High Similarity	NPC49402
0.8834	High Similarity	NPC273462
0.8834	High Similarity	NPC292214
0.8834	High Similarity	NPC89474
0.8834	High Similarity	NPC235333
0.8834	High Similarity	NPC88645
0.8834	High Similarity	NPC206238
0.8834	High Similarity	NPC70433
0.8834	High Similarity	NPC472462
0.8834	High Similarity	NPC192083
0.8834	High Similarity	NPC213896
0.8834	High Similarity	NPC271779
0.8834	High Similarity	NPC33051
0.8834	High Similarity	NPC227337
0.8824	High Similarity	NPC28042
0.8824	High Similarity	NPC472276
0.8824	High Similarity	NPC476641
0.8824	High Similarity	NPC109827
0.8824	High Similarity	NPC124470
0.882	High Similarity	NPC178202
0.882	High Similarity	NPC266499
0.882	High Similarity	NPC226644
0.882	High Similarity	NPC37226
0.8817	High Similarity	NPC470704
0.8817	High Similarity	NPC241820
0.881	High Similarity	NPC108433
0.881	High Similarity	NPC239752
0.881	High Similarity	NPC275780
0.881	High Similarity	NPC472450
0.881	High Similarity	NPC300053
0.881	High Similarity	NPC471788
0.8802	High Similarity	NPC470694
0.8802	High Similarity	NPC8300
0.88	High Similarity	NPC154527
0.8795	High Similarity	NPC476283
0.8795	High Similarity	NPC472624
0.8795	High Similarity	NPC204290

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 NPC261471 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	994
0.2-0.3	1814
0.3-0.4	2681
0.4-0.5	1845
0.5-0.6	972
0.6-0.7	307
0.7-0.8	112
0.8-0.85	43
0.85-0.9	10
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8834	High Similarity	NPD2393	Clinical (unspecified phase)
0.872	High Similarity	NPD2801	Approved
0.858	High Similarity	NPD6232	Discontinued
0.8571	High Similarity	NPD5494	Approved
0.8563	High Similarity	NPD3749	Approved
0.8547	High Similarity	NPD5844	Phase 1
0.8545	High Similarity	NPD1934	Approved
0.8538	High Similarity	NPD7473	Discontinued
0.8503	High Similarity	NPD4868	Clinical (unspecified phase)
0.8503	High Similarity	NPD3882	Suspended
0.84	Intermediate Similarity	NPD6559	Discontinued
0.8395	Intermediate Similarity	NPD1511	Approved
0.8383	Intermediate Similarity	NPD7819	Suspended
0.8382	Intermediate Similarity	NPD3818	Discontinued
0.8343	Intermediate Similarity	NPD7075	Discontinued
0.8314	Intermediate Similarity	NPD3926	Phase 2
0.8294	Intermediate Similarity	NPD919	Approved
0.8293	Intermediate Similarity	NPD1512	Approved
0.8274	Intermediate Similarity	NPD1465	Phase 2
0.8274	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD6166	Phase 2
0.8266	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7411	Suspended
0.8249	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD920	Approved
0.8232	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD3817	Phase 2
0.8198	Intermediate Similarity	NPD1247	Approved
0.8161	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD1243	Approved
0.8137	Intermediate Similarity	NPD2344	Approved
0.8121	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD4380	Phase 2
0.8079	Intermediate Similarity	NPD7074	Phase 3
0.8075	Intermediate Similarity	NPD2935	Discontinued
0.807	Intermediate Similarity	NPD7768	Phase 2
0.8034	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7054	Approved
0.8012	Intermediate Similarity	NPD2532	Approved
0.8012	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD2533	Approved
0.8012	Intermediate Similarity	NPD2534	Approved
0.8012	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD6959	Discontinued
0.7978	Intermediate Similarity	NPD7472	Approved
0.7978	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1549	Phase 2
0.7952	Intermediate Similarity	NPD6799	Approved
0.7939	Intermediate Similarity	NPD2309	Approved
0.7933	Intermediate Similarity	NPD6797	Phase 2
0.7929	Intermediate Similarity	NPD3226	Approved
0.7927	Intermediate Similarity	NPD2800	Approved
0.7919	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD5402	Approved
0.7889	Intermediate Similarity	NPD7251	Discontinued
0.7882	Intermediate Similarity	NPD6599	Discontinued
0.7818	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD1510	Phase 2
0.7771	Intermediate Similarity	NPD3750	Approved
0.7764	Intermediate Similarity	NPD1240	Approved
0.7764	Intermediate Similarity	NPD943	Approved
0.7758	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD7808	Phase 3
0.7744	Intermediate Similarity	NPD2796	Approved
0.7722	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD230	Phase 1
0.7701	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2346	Discontinued
0.7683	Intermediate Similarity	NPD2799	Discontinued
0.7676	Intermediate Similarity	NPD8434	Phase 2
0.7669	Intermediate Similarity	NPD1607	Approved
0.7637	Intermediate Similarity	NPD5953	Discontinued
0.7622	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD447	Suspended
0.7594	Intermediate Similarity	NPD4287	Approved
0.7584	Intermediate Similarity	NPD7199	Phase 2
0.7571	Intermediate Similarity	NPD6234	Discontinued
0.7569	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7229	Phase 3
0.7542	Intermediate Similarity	NPD5710	Approved
0.7542	Intermediate Similarity	NPD5711	Approved
0.7531	Intermediate Similarity	NPD2313	Discontinued
0.753	Intermediate Similarity	NPD1551	Phase 2
0.7529	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5403	Approved
0.7473	Intermediate Similarity	NPD3751	Discontinued
0.747	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3748	Approved
0.7457	Intermediate Similarity	NPD1653	Approved
0.7456	Intermediate Similarity	NPD4628	Phase 3
0.7456	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD8313	Approved
0.7419	Intermediate Similarity	NPD8312	Approved
0.7407	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD2296	Approved
0.7387	Intermediate Similarity	NPD8151	Discontinued
0.7386	Intermediate Similarity	NPD37	Approved
0.7384	Intermediate Similarity	NPD5401	Approved
0.7384	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7228	Approved
0.7366	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4967	Phase 2
0.736	Intermediate Similarity	NPD4965	Approved
0.736	Intermediate Similarity	NPD4966	Approved
0.7348	Intermediate Similarity	NPD6808	Phase 2
0.7346	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1613	Approved
0.7333	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1203	Approved
0.7326	Intermediate Similarity	NPD7390	Discontinued
0.7314	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD7783	Phase 2
0.7313	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7435	Discontinued
0.731	Intermediate Similarity	NPD6190	Approved
0.7289	Intermediate Similarity	NPD1933	Approved
0.7278	Intermediate Similarity	NPD1471	Phase 3
0.7253	Intermediate Similarity	NPD3787	Discontinued
0.7246	Intermediate Similarity	NPD6651	Approved
0.7245	Intermediate Similarity	NPD6776	Approved
0.7245	Intermediate Similarity	NPD6782	Approved
0.7245	Intermediate Similarity	NPD6778	Approved
0.7245	Intermediate Similarity	NPD6777	Approved
0.7245	Intermediate Similarity	NPD6779	Approved
0.7245	Intermediate Similarity	NPD6780	Approved
0.7245	Intermediate Similarity	NPD6781	Approved
0.7219	Intermediate Similarity	NPD5408	Approved
0.7219	Intermediate Similarity	NPD5404	Approved
0.7219	Intermediate Similarity	NPD6099	Approved
0.7219	Intermediate Similarity	NPD7685	Pre-registration
0.7219	Intermediate Similarity	NPD5405	Approved
0.7219	Intermediate Similarity	NPD6100	Approved
0.7219	Intermediate Similarity	NPD5406	Approved
0.7212	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3764	Approved
0.7212	Intermediate Similarity	NPD3268	Approved
0.7211	Intermediate Similarity	NPD8150	Discontinued
0.7195	Intermediate Similarity	NPD6832	Phase 2
0.7191	Intermediate Similarity	NPD6280	Approved
0.7191	Intermediate Similarity	NPD6279	Approved
0.7186	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7135	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5242	Approved
0.7117	Intermediate Similarity	NPD2797	Approved
0.71	Intermediate Similarity	NPD7870	Phase 2
0.71	Intermediate Similarity	NPD7871	Phase 2
0.7094	Intermediate Similarity	NPD7874	Approved
0.7094	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4908	Phase 1
0.709	Intermediate Similarity	NPD7549	Discontinued
0.7088	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4308	Phase 3
0.7059	Intermediate Similarity	NPD7033	Discontinued
0.7056	Intermediate Similarity	NPD8455	Phase 2
0.7052	Intermediate Similarity	NPD7003	Approved
0.705	Intermediate Similarity	NPD7698	Approved
0.705	Intermediate Similarity	NPD7696	Phase 3
0.705	Intermediate Similarity	NPD7697	Approved
0.7048	Intermediate Similarity	NPD3027	Phase 3
0.7048	Intermediate Similarity	NPD4625	Phase 3
0.7037	Intermediate Similarity	NPD1608	Approved
0.7022	Intermediate Similarity	NPD7458	Discontinued
0.7006	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD411	Approved
0.7005	Intermediate Similarity	NPD7177	Discontinued
0.6995	Remote Similarity	NPD7701	Phase 2
0.6994	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4360	Phase 2
0.699	Remote Similarity	NPD6534	Approved
0.699	Remote Similarity	NPD4363	Phase 3
0.699	Remote Similarity	NPD6535	Approved
0.6982	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5124	Phase 1
0.6975	Remote Similarity	NPD422	Phase 1
0.697	Remote Similarity	NPD2798	Approved
0.6964	Remote Similarity	NPD6233	Phase 2
0.6961	Remote Similarity	NPD5761	Phase 2
0.6961	Remote Similarity	NPD5760	Phase 2
0.6954	Remote Similarity	NPD4361	Phase 2
0.6954	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6273	Approved
0.6947	Remote Similarity	NPD7240	Approved
0.694	Remote Similarity	NPD6971	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