NPASS Compound

Structure

NPC290671 OpenBabel07101719122D 30 33 0 0 1 0 0 0 0 0999 V2000 1.8171 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0850 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 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 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 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 1.8171 -2.8090 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 14 2 0 0 0 0 4 14 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 15 2 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 10 18 1 0 0 0 0 11 17 1 0 0 0 0 11 19 1 0 0 0 0 12 16 2 0 0 0 0 12 20 1 0 0 0 0 15 16 1 0 0 0 0 16 21 1 0 0 0 0 17 24 2 0 0 0 0 17 25 1 0 0 0 0 18 22 1 0 0 0 0 18 26 2 0 0 0 0 19 14 1 1 0 0 0 19 29 1 0 0 0 0 20 27 2 0 0 0 0 20 30 1 0 0 0 0 21 23 2 0 0 0 0 21 24 1 0 0 0 0 22 23 1 0 0 0 0 22 25 2 0 0 0 0 23 28 1 0 0 0 0 24 30 1 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.16
Volume:	424.317
LogP:	5.961
LogD:	4.014
LogS:	-4.985
# Rotatable Bonds:	5
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.356
Synthetic Accessibility Score:	3.423
Fsp3:	0.28
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.715
MDCK Permeability:	2.0386261894600466e-05
Pgp-inhibitor:	0.95
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	97.16577911376953%
Volume Distribution (VD):	0.798
Pgp-substrate:	1.4701398611068726%

ADMET: Metabolism

CYP1A2-inhibitor:	0.286
CYP1A2-substrate:	0.611
CYP2C19-inhibitor:	0.831
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.822
CYP2C9-substrate:	0.886
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.449
CYP3A4-inhibitor:	0.17
CYP3A4-substrate:	0.18

ADMET: Excretion

Clearance (CL):	8.32
Half-life (T1/2):	0.067

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.943
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.252
Rat Oral Acute Toxicity:	0.855
Maximum Recommended Daily Dose:	0.818
Skin Sensitization:	0.43
Carcinogencity:	0.771
Eye Corrosion:	0.003
Eye Irritation:	0.122
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC290671

Natural Product ID:	NPC290671
*Common Name:**	(8S)-5-Hydroxy-6-(3-Methylbutanoyl)-4-Phenyl-8-Prop-1-En-2-Yl-8,9-Dihydrofuro[2,3-H]Chromen-2-One
IUPAC Name:	(8S)-5-hydroxy-6-(3-methylbutanoyl)-4-phenyl-8-prop-1-en-2-yl-8,9-dihydrofuro[2,3-h]chromen-2-one
Synonyms:
Standard InCHIKey:	RFHMEYQQYUJGMP-IBGZPJMESA-N
Standard InCHI:	InChI=1S/C25H24O5/c1-13(2)10-18(26)22-23(28)21-16(15-8-6-5-7-9-15)12-20(27)30-24(21)17-11-19(14(3)4)29-25(17)22/h5-9,12-13,19,28H,3,10-11H2,1-2,4H3/t19-/m0/s1
SMILES:	CC(C)CC(=O)c1c(c2c(cc(=O)oc2c2C[C@@H](C(=C)C)Oc12)c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL514528
PubChem CID:	11112232
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0003650] Prenylated neoflavonoids

*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
NPO27228	Calophyllum dispar	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374944]
NPO27228	Calophyllum dispar	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	40.0	ug ml-1	PMID[454859]

☑ 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 NPC290671 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	358
0.1-0.2	1432
0.2-0.3	3362
0.3-0.4	7647
0.4-0.5	11060
0.5-0.6	4032
0.6-0.7	5536
0.7-0.8	4947
0.8-0.85	2713
0.85-0.9	1322
0.9-0.95	249
0.95-1	39

Similarity Score	Similarity Level	Natural Product ID
0.9793	High Similarity	NPC474735
0.973	High Similarity	NPC474609
0.973	High Similarity	NPC129053
0.973	High Similarity	NPC109967
0.973	High Similarity	NPC469936
0.973	High Similarity	NPC474738
0.973	High Similarity	NPC321372
0.973	High Similarity	NPC475797
0.973	High Similarity	NPC78554
0.9662	High Similarity	NPC279218
0.9662	High Similarity	NPC108937
0.9653	High Similarity	NPC470322
0.9589	High Similarity	NPC19238
0.9583	High Similarity	NPC196137
0.9583	High Similarity	NPC1886
0.9521	High Similarity	NPC168085
0.9517	High Similarity	NPC154217
0.9517	High Similarity	NPC181388
0.9514	High Similarity	NPC188632
0.9514	High Similarity	NPC94794
0.9514	High Similarity	NPC470296
0.9514	High Similarity	NPC87609
0.9514	High Similarity	NPC196459
0.9514	High Similarity	NPC112791
0.9459	High Similarity	NPC312549
0.9459	High Similarity	NPC209142
0.9456	High Similarity	NPC104236
0.9456	High Similarity	NPC164205
0.9456	High Similarity	NPC317492
0.9448	High Similarity	NPC469935
0.9448	High Similarity	NPC178627
0.9444	High Similarity	NPC472344
0.9444	High Similarity	NPC470556
0.9444	High Similarity	NPC36181
0.94	High Similarity	NPC469934
0.9392	High Similarity	NPC476185
0.9392	High Similarity	NPC321896
0.9388	High Similarity	NPC161864
0.9388	High Similarity	NPC208303
0.9379	High Similarity	NPC96216
0.9379	High Similarity	NPC470553
0.9379	High Similarity	NPC307895
0.9379	High Similarity	NPC474939
0.9379	High Similarity	NPC470909
0.9329	High Similarity	NPC471675
0.9324	High Similarity	NPC469932
0.932	High Similarity	NPC249942
0.932	High Similarity	NPC140120
0.932	High Similarity	NPC285748
0.932	High Similarity	NPC297886
0.9315	High Similarity	NPC469953
0.9315	High Similarity	NPC224714
0.9315	High Similarity	NPC133060
0.9315	High Similarity	NPC288910
0.9315	High Similarity	NPC118059
0.9315	High Similarity	NPC470554
0.931	High Similarity	NPC112829
0.931	High Similarity	NPC294432
0.9267	High Similarity	NPC476238
0.9267	High Similarity	NPC327269
0.9267	High Similarity	NPC31627
0.9262	High Similarity	NPC470908
0.9262	High Similarity	NPC327059
0.9262	High Similarity	NPC321387
0.9257	High Similarity	NPC469933
0.9252	High Similarity	NPC474161
0.9252	High Similarity	NPC472629
0.9252	High Similarity	NPC57470
0.9252	High Similarity	NPC470910
0.9252	High Similarity	NPC476088
0.9247	High Similarity	NPC223812
0.9247	High Similarity	NPC107177
0.9247	High Similarity	NPC85162
0.9247	High Similarity	NPC77794
0.9247	High Similarity	NPC81697
0.9247	High Similarity	NPC278249
0.9247	High Similarity	NPC184738
0.9247	High Similarity	NPC33653
0.9247	High Similarity	NPC125894
0.9241	High Similarity	NPC110038
0.9241	High Similarity	NPC282300
0.9241	High Similarity	NPC248372
0.9236	High Similarity	NPC217186
0.9236	High Similarity	NPC473209
0.9236	High Similarity	NPC53181
0.9221	High Similarity	NPC92589
0.92	High Similarity	NPC472636
0.92	High Similarity	NPC317715
0.92	High Similarity	NPC148945
0.92	High Similarity	NPC78835
0.92	High Similarity	NPC309512
0.92	High Similarity	NPC204561
0.92	High Similarity	NPC316960
0.9195	High Similarity	NPC5173
0.9195	High Similarity	NPC470461
0.9189	High Similarity	NPC177995
0.9189	High Similarity	NPC308200
0.9189	High Similarity	NPC473077
0.9189	High Similarity	NPC474108
0.9189	High Similarity	NPC180477
0.9189	High Similarity	NPC296998
0.9184	High Similarity	NPC235217
0.9184	High Similarity	NPC473015
0.9184	High Similarity	NPC131568
0.9184	High Similarity	NPC326500
0.9184	High Similarity	NPC473014
0.9184	High Similarity	NPC273538
0.9184	High Similarity	NPC271288
0.9184	High Similarity	NPC131579
0.9184	High Similarity	NPC470890
0.9184	High Similarity	NPC473013
0.9184	High Similarity	NPC87486
0.9184	High Similarity	NPC319752
0.9184	High Similarity	NPC216538
0.9184	High Similarity	NPC124780
0.9178	High Similarity	NPC227579
0.9178	High Similarity	NPC37496
0.9178	High Similarity	NPC107572
0.9178	High Similarity	NPC78
0.9178	High Similarity	NPC166482
0.9178	High Similarity	NPC40833
0.9178	High Similarity	NPC76338
0.9178	High Similarity	NPC306829
0.9178	High Similarity	NPC76372
0.9178	High Similarity	NPC166934
0.9178	High Similarity	NPC148757
0.9178	High Similarity	NPC125855
0.9178	High Similarity	NPC167624
0.9178	High Similarity	NPC1089
0.9178	High Similarity	NPC194432
0.9178	High Similarity	NPC220998
0.9178	High Similarity	NPC32739
0.9178	High Similarity	NPC328164
0.9178	High Similarity	NPC265040
0.9178	High Similarity	NPC228504
0.9178	High Similarity	NPC324436
0.9178	High Similarity	NPC177354
0.9178	High Similarity	NPC223500
0.9178	High Similarity	NPC10937
0.9178	High Similarity	NPC296917
0.9178	High Similarity	NPC64915
0.9178	High Similarity	NPC66515
0.9178	High Similarity	NPC324134
0.9178	High Similarity	NPC182852
0.9178	High Similarity	NPC161506
0.9172	High Similarity	NPC159275
0.9172	High Similarity	NPC241100
0.9167	High Similarity	NPC199458
0.9167	High Similarity	NPC183639
0.915	High Similarity	NPC269495
0.9139	High Similarity	NPC473996
0.9139	High Similarity	NPC285623
0.9133	High Similarity	NPC37348
0.9133	High Similarity	NPC29777
0.9133	High Similarity	NPC472633
0.9133	High Similarity	NPC61258
0.9133	High Similarity	NPC471115
0.9133	High Similarity	NPC180351
0.9133	High Similarity	NPC472421
0.9128	High Similarity	NPC470460
0.9128	High Similarity	NPC39195
0.9128	High Similarity	NPC145467
0.9122	High Similarity	NPC301276
0.9122	High Similarity	NPC214774
0.9122	High Similarity	NPC187282
0.9122	High Similarity	NPC24136
0.9122	High Similarity	NPC20488
0.9122	High Similarity	NPC312973
0.9122	High Similarity	NPC178343
0.9122	High Similarity	NPC83357
0.9122	High Similarity	NPC475052
0.9122	High Similarity	NPC306488
0.9122	High Similarity	NPC285630
0.9122	High Similarity	NPC267375
0.9122	High Similarity	NPC54577
0.9122	High Similarity	NPC142405
0.9122	High Similarity	NPC470647
0.9122	High Similarity	NPC127059
0.9122	High Similarity	NPC246948
0.9122	High Similarity	NPC195621
0.9122	High Similarity	NPC67805
0.9122	High Similarity	NPC176229
0.9122	High Similarity	NPC290133
0.9122	High Similarity	NPC5820
0.9122	High Similarity	NPC88964
0.9122	High Similarity	NPC124729
0.9122	High Similarity	NPC111786
0.9116	High Similarity	NPC475705
0.9116	High Similarity	NPC185276
0.9116	High Similarity	NPC143896
0.9116	High Similarity	NPC51887
0.9116	High Similarity	NPC24821
0.9116	High Similarity	NPC91560
0.9116	High Similarity	NPC316816
0.9116	High Similarity	NPC150408
0.9116	High Similarity	NPC476178
0.9116	High Similarity	NPC75049
0.9116	High Similarity	NPC9117
0.9116	High Similarity	NPC293053
0.9116	High Similarity	NPC39329

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 NPC290671 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	895
0.2-0.3	1577
0.3-0.4	2481
0.4-0.5	2111
0.5-0.6	1151
0.6-0.7	412
0.7-0.8	135
0.8-0.85	47
0.85-0.9	24
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9184	High Similarity	NPD4378	Clinical (unspecified phase)
0.8903	High Similarity	NPD7075	Discontinued
0.8836	High Similarity	NPD1552	Clinical (unspecified phase)
0.8836	High Similarity	NPD1550	Clinical (unspecified phase)
0.8831	High Similarity	NPD7096	Clinical (unspecified phase)
0.8831	High Similarity	NPD2393	Clinical (unspecified phase)
0.8824	High Similarity	NPD7411	Suspended
0.88	High Similarity	NPD7410	Clinical (unspecified phase)
0.8776	High Similarity	NPD1549	Phase 2
0.8774	High Similarity	NPD8443	Clinical (unspecified phase)
0.8767	High Similarity	NPD2796	Approved
0.8766	High Similarity	NPD6801	Discontinued
0.8758	High Similarity	NPD4380	Phase 2
0.871	High Similarity	NPD7819	Suspended
0.8699	High Similarity	NPD1510	Phase 2
0.8684	High Similarity	NPD920	Approved
0.8591	High Similarity	NPD1243	Approved
0.8553	High Similarity	NPD642	Clinical (unspecified phase)
0.8553	High Similarity	NPD2533	Approved
0.8553	High Similarity	NPD2534	Approved
0.8553	High Similarity	NPD2532	Approved
0.8544	High Similarity	NPD4381	Clinical (unspecified phase)
0.8543	High Similarity	NPD643	Clinical (unspecified phase)
0.8526	High Similarity	NPD1934	Approved
0.8487	Intermediate Similarity	NPD6799	Approved
0.8481	Intermediate Similarity	NPD7768	Phase 2
0.8467	Intermediate Similarity	NPD2800	Approved
0.8467	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD3749	Approved
0.8425	Intermediate Similarity	NPD1240	Approved
0.8418	Intermediate Similarity	NPD3817	Phase 2
0.8415	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD3750	Approved
0.84	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD1511	Approved
0.8354	Intermediate Similarity	NPD3818	Discontinued
0.8354	Intermediate Similarity	NPD2801	Approved
0.8323	Intermediate Similarity	NPD5494	Approved
0.8311	Intermediate Similarity	NPD1607	Approved
0.8288	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD2313	Discontinued
0.828	Intermediate Similarity	NPD6599	Discontinued
0.8272	Intermediate Similarity	NPD6959	Discontinued
0.8267	Intermediate Similarity	NPD2935	Discontinued
0.8267	Intermediate Similarity	NPD1551	Phase 2
0.8263	Intermediate Similarity	NPD6559	Discontinued
0.8258	Intermediate Similarity	NPD1512	Approved
0.825	Intermediate Similarity	NPD3882	Suspended
0.8214	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD5403	Approved
0.82	Intermediate Similarity	NPD2799	Discontinued
0.8182	Intermediate Similarity	NPD7473	Discontinued
0.8148	Intermediate Similarity	NPD919	Approved
0.8137	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6166	Phase 2
0.8121	Intermediate Similarity	NPD5124	Phase 1
0.811	Intermediate Similarity	NPD6232	Discontinued
0.8095	Intermediate Similarity	NPD5953	Discontinued
0.8084	Intermediate Similarity	NPD5844	Phase 1
0.8084	Intermediate Similarity	NPD7286	Phase 2
0.8084	Intermediate Similarity	NPD7054	Approved
0.8079	Intermediate Similarity	NPD7033	Discontinued
0.8079	Intermediate Similarity	NPD3748	Approved
0.8077	Intermediate Similarity	NPD5401	Approved
0.8075	Intermediate Similarity	NPD5402	Approved
0.8067	Intermediate Similarity	NPD6651	Approved
0.8052	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD3268	Approved
0.8036	Intermediate Similarity	NPD7074	Phase 3
0.8036	Intermediate Similarity	NPD7472	Approved
0.8	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6797	Phase 2
0.7987	Intermediate Similarity	NPD3226	Approved
0.7945	Intermediate Similarity	NPD1203	Approved
0.7945	Intermediate Similarity	NPD2797	Approved
0.7941	Intermediate Similarity	NPD7251	Discontinued
0.7935	Intermediate Similarity	NPD4628	Phase 3
0.7905	Intermediate Similarity	NPD6832	Phase 2
0.7895	Intermediate Similarity	NPD7808	Phase 3
0.7892	Intermediate Similarity	NPD5710	Approved
0.7892	Intermediate Similarity	NPD5711	Approved
0.7888	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2346	Discontinued
0.7857	Intermediate Similarity	NPD2344	Approved
0.78	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD422	Phase 1
0.7784	Intermediate Similarity	NPD7229	Phase 3
0.7753	Intermediate Similarity	NPD4363	Phase 3
0.7753	Intermediate Similarity	NPD4360	Phase 2
0.7742	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6005	Phase 3
0.7742	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6002	Phase 3
0.7742	Intermediate Similarity	NPD6004	Phase 3
0.774	Intermediate Similarity	NPD9717	Approved
0.7736	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4308	Phase 3
0.7725	Intermediate Similarity	NPD1247	Approved
0.7709	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD4361	Phase 2
0.7707	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD3267	Approved
0.7703	Intermediate Similarity	NPD3266	Approved
0.7674	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD4908	Phase 1
0.7667	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2309	Approved
0.7651	Intermediate Similarity	NPD2798	Approved
0.7647	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD3225	Approved
0.7576	Intermediate Similarity	NPD1465	Phase 2
0.7564	Intermediate Similarity	NPD6099	Approved
0.7564	Intermediate Similarity	NPD6100	Approved
0.7551	Intermediate Similarity	NPD1610	Phase 2
0.7551	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7458	Discontinued
0.7532	Intermediate Similarity	NPD6355	Discontinued
0.7528	Intermediate Similarity	NPD4287	Approved
0.7517	Intermediate Similarity	NPD1548	Phase 1
0.7515	Intermediate Similarity	NPD37	Approved
0.7515	Intermediate Similarity	NPD7199	Phase 2
0.7514	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6234	Discontinued
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7469	Intermediate Similarity	NPD6273	Approved
0.7468	Intermediate Similarity	NPD4307	Phase 2
0.7455	Intermediate Similarity	NPD5889	Approved
0.7455	Intermediate Similarity	NPD5890	Approved
0.7453	Intermediate Similarity	NPD7390	Discontinued
0.7453	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD3764	Approved
0.7451	Intermediate Similarity	NPD6798	Discontinued
0.7451	Intermediate Similarity	NPD1296	Phase 2
0.7444	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD8313	Approved
0.7443	Intermediate Similarity	NPD8312	Approved
0.7427	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD3926	Phase 2
0.7425	Intermediate Similarity	NPD4288	Approved
0.7421	Intermediate Similarity	NPD2654	Approved
0.7421	Intermediate Similarity	NPD1652	Phase 2
0.7419	Intermediate Similarity	NPD447	Suspended
0.7419	Intermediate Similarity	NPD230	Phase 1
0.7417	Intermediate Similarity	NPD1019	Discontinued
0.7414	Intermediate Similarity	NPD1729	Discontinued
0.7397	Intermediate Similarity	NPD9545	Approved
0.7375	Intermediate Similarity	NPD7003	Approved
0.7355	Intermediate Similarity	NPD943	Approved
0.7342	Intermediate Similarity	NPD5404	Approved
0.7342	Intermediate Similarity	NPD5405	Approved
0.7342	Intermediate Similarity	NPD5406	Approved
0.7342	Intermediate Similarity	NPD5408	Approved
0.7338	Intermediate Similarity	NPD411	Approved
0.7333	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1933	Approved
0.7302	Intermediate Similarity	NPD7584	Approved
0.7297	Intermediate Similarity	NPD17	Approved
0.729	Intermediate Similarity	NPD6233	Phase 2
0.7289	Intermediate Similarity	NPD6585	Discontinued
0.7283	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6808	Phase 2
0.7263	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5760	Phase 2
0.7262	Intermediate Similarity	NPD8455	Phase 2
0.7262	Intermediate Similarity	NPD5761	Phase 2
0.726	Intermediate Similarity	NPD9493	Approved
0.7255	Intermediate Similarity	NPD2861	Phase 2
0.7244	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4060	Phase 1
0.7244	Intermediate Similarity	NPD1613	Approved
0.7237	Intermediate Similarity	NPD1164	Approved
0.7233	Intermediate Similarity	NPD4476	Approved
0.7233	Intermediate Similarity	NPD4477	Approved
0.72	Intermediate Similarity	NPD7228	Approved
0.719	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD2403	Approved
0.7173	Intermediate Similarity	NPD7585	Approved
0.7169	Intermediate Similarity	NPD1653	Approved
0.7162	Intermediate Similarity	NPD1894	Discontinued
0.7161	Intermediate Similarity	NPD4625	Phase 3
0.7152	Intermediate Similarity	NPD5049	Phase 3
0.7152	Intermediate Similarity	NPD1481	Phase 2
0.7143	Intermediate Similarity	NPD2424	Discontinued
0.7135	Intermediate Similarity	NPD6971	Discontinued
0.7127	Intermediate Similarity	NPD8150	Discontinued
0.712	Intermediate Similarity	NPD7583	Approved
0.7118	Intermediate Similarity	NPD2296	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data