NPASS Compound

Structure

CID142527 OpenBabel06191715502D 36 39 0 0 0 0 0 0 0 0999 V2000 8.6603 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -5.5000 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 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -0.3660 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 6.9282 -4.0000 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 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 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 6.0622 -2.5000 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 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 5.1962 -3.0000 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 1.7321 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 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 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 7 9 1 0 0 0 0 7 16 2 0 0 0 0 8 12 1 0 0 0 0 8 17 2 0 0 0 0 9 18 1 0 0 0 0 10 11 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 30 1 0 0 0 0 15 19 2 0 0 0 0 15 22 1 0 0 0 0 18 22 2 0 0 0 0 19 27 1 0 0 0 0 20 24 2 0 0 0 0 20 28 1 0 0 0 0 21 24 1 0 0 0 0 21 29 2 0 0 0 0 22 31 1 0 0 0 0 23 25 1 0 0 0 0 23 28 2 0 0 0 0 23 29 1 0 0 0 0 24 32 1 0 0 0 0 25 26 1 0 0 0 0 25 33 2 0 0 0 0 26 27 2 0 0 0 0 26 34 1 0 0 0 0 27 35 1 0 0 0 0 28 35 1 0 0 0 0 29 36 1 0 0 0 0 30 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.24
Volume:	519.587
LogP:	7.775
LogD:	4.143
LogS:	-2.324
# Rotatable Bonds:	5
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.344
Synthetic Accessibility Score:	3.444
Fsp3:	0.367
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.81
MDCK Permeability:	1.5453601008630358e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.085
20% Bioavailability (F20%):	0.423
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	92.6381607055664%
Volume Distribution (VD):	1.083
Pgp-substrate:	10.634649276733398%

ADMET: Metabolism

CYP1A2-inhibitor:	0.235
CYP1A2-substrate:	0.191
CYP2C19-inhibitor:	0.71
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.664
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.133
CYP3A4-substrate:	0.062

ADMET: Excretion

Clearance (CL):	5.311
Half-life (T1/2):	0.074

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.955
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.077
Rat Oral Acute Toxicity:	0.71
Maximum Recommended Daily Dose:	0.086
Skin Sensitization:	0.732
Carcinogencity:	0.062
Eye Corrosion:	0.003
Eye Irritation:	0.212
Respiratory Toxicity:	0.142

Download Data

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

Natural Product: NPC142527

Natural Product ID:	NPC142527
*Common Name:**	Dorsilurin J
IUPAC Name:	5,9-dihydroxy-8-[3-hydroxy-4-(3-methylbut-2-enyl)phenyl]-2,2-dimethyl-6-(3-methylbut-2-enyl)-3,4-dihydropyrano[2,3-f]chromen-10-one
Synonyms:	dorsilurin J
Standard InCHIKey:	MBIMXMBSWOGVPF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H34O6/c1-16(2)7-9-18-10-11-19(15-22(18)31)27-26(34)25(33)23-28(35-27)20(12-8-17(3)4)24(32)21-13-14-30(5,6)36-29(21)23/h7-8,10-11,15,31-32,34H,9,12-14H2,1-6H3
SMILES:	CC(=CCc1ccc(cc1O)c1oc2c(CC=C(C)C)c(O)c3c(c2c(=O)c1O)OC(CC3)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455685
PubChem CID:	25180898
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003504] 8-prenylated flavones

*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
NPO4673	Dorstenia psilurus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19061390]
NPO4673	Dorstenia psilurus	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[19061390]
NPO4673	Dorstenia psilurus	Species	Moraceae	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	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	IC50	=	16910.0	nM	PMID[551419]
NPT2	Others	Unspecified	IC50	=	316550.0	nM	PMID[551419]
NPT2	Others	Unspecified	IC50	=	518270.0	nM	PMID[551419]

☑ 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 NPC142527 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	454
0.1-0.2	1869
0.2-0.3	4597
0.3-0.4	10875
0.4-0.5	6931
0.5-0.6	3773
0.6-0.7	5224
0.7-0.8	4659
0.8-0.85	2486
0.85-0.9	1346
0.9-0.95	437
0.95-1	46

Similarity Score	Similarity Level	Natural Product ID
0.9864	High Similarity	NPC275575
0.9863	High Similarity	NPC45934
0.9793	High Similarity	NPC269420
0.9732	High Similarity	NPC281137
0.9732	High Similarity	NPC282390
0.9589	High Similarity	NPC296869
0.953	High Similarity	NPC193200
0.9521	High Similarity	NPC14001
0.9521	High Similarity	NPC166757
0.9459	High Similarity	NPC472633
0.9456	High Similarity	NPC244407
0.9452	High Similarity	NPC124729
0.9452	High Similarity	NPC220418
0.9448	High Similarity	NPC24821
0.9448	High Similarity	NPC293053
0.9448	High Similarity	NPC219915
0.9448	High Similarity	NPC212932
0.9448	High Similarity	NPC9117
0.9448	High Similarity	NPC190637
0.9384	High Similarity	NPC326500
0.9384	High Similarity	NPC273538
0.9384	High Similarity	NPC216538
0.9379	High Similarity	NPC473042
0.9379	High Similarity	NPC200694
0.9342	High Similarity	NPC237418
0.9329	High Similarity	NPC101957
0.9329	High Similarity	NPC120105
0.932	High Similarity	NPC5820
0.932	High Similarity	NPC196114
0.932	High Similarity	NPC178343
0.932	High Similarity	NPC306488
0.9315	High Similarity	NPC38219
0.9272	High Similarity	NPC311579
0.9272	High Similarity	NPC95842
0.9272	High Similarity	NPC329844
0.9272	High Similarity	NPC210942
0.9272	High Similarity	NPC178964
0.9272	High Similarity	NPC280530
0.9272	High Similarity	NPC236756
0.9272	High Similarity	NPC169990
0.9262	High Similarity	NPC223988
0.9262	High Similarity	NPC474052
0.9257	High Similarity	NPC473077
0.9257	High Similarity	NPC296998
0.9257	High Similarity	NPC283234
0.9247	High Similarity	NPC78803
0.9247	High Similarity	NPC59739
0.9247	High Similarity	NPC299080
0.9247	High Similarity	NPC144499
0.9247	High Similarity	NPC293852
0.9247	High Similarity	NPC214236
0.9247	High Similarity	NPC217083
0.9247	High Similarity	NPC62840
0.9211	High Similarity	NPC207809
0.9211	High Similarity	NPC476169
0.9211	High Similarity	NPC259710
0.9211	High Similarity	NPC48579
0.9211	High Similarity	NPC304207
0.9211	High Similarity	NPC217706
0.9205	High Similarity	NPC63187
0.9205	High Similarity	NPC157784
0.9205	High Similarity	NPC37684
0.92	High Similarity	NPC29777
0.92	High Similarity	NPC471115
0.92	High Similarity	NPC61258
0.9195	High Similarity	NPC37135
0.9195	High Similarity	NPC132592
0.9195	High Similarity	NPC160821
0.9195	High Similarity	NPC186397
0.9189	High Similarity	NPC24136
0.9189	High Similarity	NPC312973
0.9189	High Similarity	NPC88964
0.9189	High Similarity	NPC187282
0.9189	High Similarity	NPC111786
0.9189	High Similarity	NPC20488
0.9189	High Similarity	NPC290133
0.9189	High Similarity	NPC195621
0.9189	High Similarity	NPC267375
0.9189	High Similarity	NPC54577
0.9189	High Similarity	NPC475052
0.9189	High Similarity	NPC83357
0.9189	High Similarity	NPC470647
0.9189	High Similarity	NPC67805
0.9189	High Similarity	NPC176229
0.9189	High Similarity	NPC142405
0.9189	High Similarity	NPC246948
0.9189	High Similarity	NPC301276
0.9189	High Similarity	NPC214774
0.9184	High Similarity	NPC18585
0.9184	High Similarity	NPC166138
0.9184	High Similarity	NPC106985
0.9184	High Similarity	NPC158874
0.9178	High Similarity	NPC64908
0.9178	High Similarity	NPC156590
0.9178	High Similarity	NPC118840
0.9178	High Similarity	NPC147688
0.9178	High Similarity	NPC205006
0.9172	High Similarity	NPC220062
0.9172	High Similarity	NPC55018
0.9172	High Similarity	NPC301217
0.9172	High Similarity	NPC303633
0.9172	High Similarity	NPC96565
0.9172	High Similarity	NPC216978
0.9145	High Similarity	NPC100134
0.9145	High Similarity	NPC170492
0.9145	High Similarity	NPC209760
0.9145	High Similarity	NPC248793
0.9145	High Similarity	NPC180301
0.9139	High Similarity	NPC205046
0.9139	High Similarity	NPC59162
0.9139	High Similarity	NPC304295
0.9139	High Similarity	NPC478148
0.9133	High Similarity	NPC97028
0.9133	High Similarity	NPC10027
0.9133	High Similarity	NPC97029
0.9133	High Similarity	NPC65589
0.9133	High Similarity	NPC288036
0.9133	High Similarity	NPC5173
0.9133	High Similarity	NPC470461
0.9133	High Similarity	NPC266499
0.9133	High Similarity	NPC158338
0.9133	High Similarity	NPC100985
0.9133	High Similarity	NPC65775
0.9128	High Similarity	NPC104406
0.9128	High Similarity	NPC24673
0.9128	High Similarity	NPC201731
0.9128	High Similarity	NPC79469
0.9128	High Similarity	NPC110303
0.9128	High Similarity	NPC97716
0.9128	High Similarity	NPC140120
0.9128	High Similarity	NPC23728
0.9128	High Similarity	NPC237635
0.9122	High Similarity	NPC234629
0.9122	High Similarity	NPC311741
0.9116	High Similarity	NPC226636
0.9116	High Similarity	NPC1534
0.9116	High Similarity	NPC11561
0.911	High Similarity	NPC159275
0.911	High Similarity	NPC235239
0.911	High Similarity	NPC261227
0.911	High Similarity	NPC241100
0.911	High Similarity	NPC475680
0.911	High Similarity	NPC69769
0.911	High Similarity	NPC172986
0.911	High Similarity	NPC150522
0.911	High Similarity	NPC270883
0.911	High Similarity	NPC305355
0.9103	High Similarity	NPC201395
0.9097	High Similarity	NPC172687
0.9091	High Similarity	NPC201127
0.9091	High Similarity	NPC218871
0.9091	High Similarity	NPC210048
0.9091	High Similarity	NPC476630
0.9091	High Similarity	NPC473272
0.9091	High Similarity	NPC273843
0.9091	High Similarity	NPC284820
0.9085	High Similarity	NPC304745
0.9085	High Similarity	NPC111341
0.9085	High Similarity	NPC55662
0.9085	High Similarity	NPC166054
0.9085	High Similarity	NPC133392
0.9079	High Similarity	NPC217447
0.9079	High Similarity	NPC210597
0.9079	High Similarity	NPC138288
0.9073	High Similarity	NPC88804
0.9073	High Similarity	NPC188403
0.9073	High Similarity	NPC37348
0.9073	High Similarity	NPC227122
0.9073	High Similarity	NPC3825
0.9067	High Similarity	NPC145467
0.9067	High Similarity	NPC6511
0.9067	High Similarity	NPC470460
0.9067	High Similarity	NPC27221
0.9067	High Similarity	NPC256672
0.9067	High Similarity	NPC7025
0.9067	High Similarity	NPC161191
0.9067	High Similarity	NPC266572
0.906	High Similarity	NPC285630
0.906	High Similarity	NPC127059
0.906	High Similarity	NPC470458
0.906	High Similarity	NPC329678
0.906	High Similarity	NPC473132
0.906	High Similarity	NPC473135
0.906	High Similarity	NPC472629
0.906	High Similarity	NPC470676
0.906	High Similarity	NPC477955
0.9054	High Similarity	NPC478086
0.9054	High Similarity	NPC185276
0.9054	High Similarity	NPC316816
0.9054	High Similarity	NPC214166
0.9054	High Similarity	NPC11700
0.9048	High Similarity	NPC282300
0.9048	High Similarity	NPC14871
0.9048	High Similarity	NPC110969
0.9048	High Similarity	NPC103362
0.9048	High Similarity	NPC262094
0.9048	High Similarity	NPC90582
0.9045	High Similarity	NPC207690
0.9045	High Similarity	NPC472625
0.9041	High Similarity	NPC217186

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 NPC142527 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	408
0.1-0.2	1002
0.2-0.3	1722
0.3-0.4	2706
0.4-0.5	1802
0.5-0.6	980
0.6-0.7	348
0.7-0.8	128
0.8-0.85	38
0.85-0.9	11
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9384	High Similarity	NPD4378	Clinical (unspecified phase)
0.8993	High Similarity	NPD7410	Clinical (unspecified phase)
0.8896	High Similarity	NPD2393	Clinical (unspecified phase)
0.8808	High Similarity	NPD1512	Approved
0.8726	High Similarity	NPD7075	Discontinued
0.8718	High Similarity	NPD8443	Clinical (unspecified phase)
0.8701	High Similarity	NPD4380	Phase 2
0.8679	High Similarity	NPD6959	Discontinued
0.8675	High Similarity	NPD1511	Approved
0.8654	High Similarity	NPD7096	Clinical (unspecified phase)
0.8654	High Similarity	NPD7819	Suspended
0.8649	High Similarity	NPD1552	Clinical (unspecified phase)
0.8649	High Similarity	NPD1550	Clinical (unspecified phase)
0.8591	High Similarity	NPD1549	Phase 2
0.859	High Similarity	NPD1934	Approved
0.8589	High Similarity	NPD7804	Clinical (unspecified phase)
0.8535	High Similarity	NPD2801	Approved
0.8526	High Similarity	NPD7411	Suspended
0.8519	High Similarity	NPD6167	Clinical (unspecified phase)
0.8519	High Similarity	NPD6168	Clinical (unspecified phase)
0.8519	High Similarity	NPD6166	Phase 2
0.8514	High Similarity	NPD1510	Phase 2
0.8503	High Similarity	NPD1607	Approved
0.8456	Intermediate Similarity	NPD2796	Approved
0.8375	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD1240	Approved
0.8365	Intermediate Similarity	NPD3817	Phase 2
0.8354	Intermediate Similarity	NPD6801	Discontinued
0.8333	Intermediate Similarity	NPD6099	Approved
0.8333	Intermediate Similarity	NPD6100	Approved
0.8323	Intermediate Similarity	NPD7251	Discontinued
0.8313	Intermediate Similarity	NPD3882	Suspended
0.8274	Intermediate Similarity	NPD7808	Phase 3
0.8263	Intermediate Similarity	NPD6797	Phase 2
0.8253	Intermediate Similarity	NPD7054	Approved
0.8242	Intermediate Similarity	NPD7473	Discontinued
0.8235	Intermediate Similarity	NPD3750	Approved
0.8228	Intermediate Similarity	NPD6599	Discontinued
0.8204	Intermediate Similarity	NPD7074	Phase 3
0.8204	Intermediate Similarity	NPD7472	Approved
0.8199	Intermediate Similarity	NPD7768	Phase 2
0.8194	Intermediate Similarity	NPD6799	Approved
0.8182	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6232	Discontinued
0.817	Intermediate Similarity	NPD2800	Approved
0.816	Intermediate Similarity	NPD5494	Approved
0.8148	Intermediate Similarity	NPD3749	Approved
0.8141	Intermediate Similarity	NPD2532	Approved
0.8141	Intermediate Similarity	NPD2534	Approved
0.8141	Intermediate Similarity	NPD2533	Approved
0.8117	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD6559	Discontinued
0.8105	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD2935	Discontinued
0.8077	Intermediate Similarity	NPD7390	Discontinued
0.8059	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD3226	Approved
0.8039	Intermediate Similarity	NPD2346	Discontinued
0.8036	Intermediate Similarity	NPD5844	Phase 1
0.8026	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD5402	Approved
0.7976	Intermediate Similarity	NPD3818	Discontinued
0.7975	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1551	Phase 2
0.7935	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1243	Approved
0.7925	Intermediate Similarity	NPD5403	Approved
0.7919	Intermediate Similarity	NPD4625	Phase 3
0.7908	Intermediate Similarity	NPD3748	Approved
0.7898	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6651	Approved
0.7867	Intermediate Similarity	NPD2313	Discontinued
0.7867	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD920	Approved
0.7799	Intermediate Similarity	NPD5401	Approved
0.7792	Intermediate Similarity	NPD2799	Discontinued
0.7784	Intermediate Similarity	NPD1247	Approved
0.7771	Intermediate Similarity	NPD919	Approved
0.7748	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7286	Phase 2
0.7692	Intermediate Similarity	NPD2344	Approved
0.7688	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD4308	Phase 3
0.7673	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD943	Approved
0.7636	Intermediate Similarity	NPD1465	Phase 2
0.7635	Intermediate Similarity	NPD4749	Approved
0.7633	Intermediate Similarity	NPD5711	Approved
0.7633	Intermediate Similarity	NPD5710	Approved
0.763	Intermediate Similarity	NPD5953	Discontinued
0.7616	Intermediate Similarity	NPD4908	Phase 1
0.7611	Intermediate Similarity	NPD4360	Phase 2
0.7611	Intermediate Similarity	NPD4363	Phase 3
0.7588	Intermediate Similarity	NPD3926	Phase 2
0.7578	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4628	Phase 3
0.7533	Intermediate Similarity	NPD1203	Approved
0.7527	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3268	Approved
0.7516	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5406	Approved
0.7516	Intermediate Similarity	NPD5408	Approved
0.7516	Intermediate Similarity	NPD5404	Approved
0.7516	Intermediate Similarity	NPD5405	Approved
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6777	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD8313	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.75	Intermediate Similarity	NPD6779	Approved
0.7484	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5124	Phase 1
0.7483	Intermediate Similarity	NPD2798	Approved
0.7473	Intermediate Similarity	NPD7697	Approved
0.7473	Intermediate Similarity	NPD7435	Discontinued
0.7473	Intermediate Similarity	NPD7698	Approved
0.7473	Intermediate Similarity	NPD7696	Phase 3
0.7472	Intermediate Similarity	NPD8150	Discontinued
0.7457	Intermediate Similarity	NPD3751	Discontinued
0.7452	Intermediate Similarity	NPD7033	Discontinued
0.7434	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD7871	Phase 2
0.7433	Intermediate Similarity	NPD7870	Phase 2
0.7427	Intermediate Similarity	NPD3787	Discontinued
0.7419	Intermediate Similarity	NPD4307	Phase 2
0.7417	Intermediate Similarity	NPD2797	Approved
0.741	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD411	Approved
0.7394	Intermediate Similarity	NPD7458	Discontinued
0.7386	Intermediate Similarity	NPD6832	Phase 2
0.7383	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1610	Phase 2
0.7383	Intermediate Similarity	NPD1201	Approved
0.7383	Intermediate Similarity	NPD422	Phase 1
0.7365	Intermediate Similarity	NPD6844	Discontinued
0.7358	Intermediate Similarity	NPD1471	Phase 3
0.7354	Intermediate Similarity	NPD7584	Approved
0.7351	Intermediate Similarity	NPD3225	Approved
0.7347	Intermediate Similarity	NPD1548	Phase 1
0.7342	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9717	Approved
0.7333	Intermediate Similarity	NPD1608	Approved
0.7326	Intermediate Similarity	NPD7229	Phase 3
0.7318	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7701	Phase 2
0.7312	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1613	Approved
0.7303	Intermediate Similarity	NPD1470	Approved
0.7293	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4361	Phase 2
0.7283	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4288	Approved
0.7278	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD447	Suspended
0.7261	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6585	Discontinued
0.724	Intermediate Similarity	NPD7874	Approved
0.724	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6535	Approved
0.7228	Intermediate Similarity	NPD6534	Approved
0.7222	Intermediate Similarity	NPD7003	Approved
0.7219	Intermediate Similarity	NPD3972	Approved
0.7204	Intermediate Similarity	NPD7699	Phase 2
0.7204	Intermediate Similarity	NPD7700	Phase 2
0.7202	Intermediate Similarity	NPD7801	Approved
0.7202	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7783	Phase 2
0.7198	Intermediate Similarity	NPD4287	Approved
0.719	Intermediate Similarity	NPD3267	Approved
0.719	Intermediate Similarity	NPD3266	Approved
0.7188	Intermediate Similarity	NPD8151	Discontinued
0.716	Intermediate Similarity	NPD2654	Approved
0.7159	Intermediate Similarity	NPD7177	Discontinued
0.7152	Intermediate Similarity	NPD230	Phase 1
0.7143	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6823	Phase 2
0.7143	Intermediate Similarity	NPD6671	Approved
0.7134	Intermediate Similarity	NPD3300	Phase 2
0.7133	Intermediate Similarity	NPD17	Approved
0.7118	Intermediate Similarity	NPD5761	Phase 2
0.7118	Intermediate Similarity	NPD5760	Phase 2
0.7115	Intermediate Similarity	NPD7095	Approved
0.7108	Intermediate Similarity	NPD5049	Phase 3
0.7101	Intermediate Similarity	NPD5889	Approved
0.7101	Intermediate Similarity	NPD5890	Approved
0.7097	Intermediate Similarity	NPD2861	Phase 2
0.7091	Intermediate Similarity	NPD6143	Clinical (unspecified phase)

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