NPASS Compound

Structure

NPC474735 OpenBabel07101718292D 31 33 0 0 1 0 0 0 0 0999 V2000 0.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 -4.3301 -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 -3.4641 -3.0000 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 -2.5000 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 1.7321 -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 0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 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 -0.0000 -3.0000 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 -2.5000 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 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 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 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 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 19 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 16 2 0 0 0 0 12 20 1 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 16 21 1 0 0 0 0 17 23 1 0 0 0 0 17 25 2 0 0 0 0 18 26 1 0 0 0 0 19 22 1 0 0 0 0 19 27 2 0 0 0 0 20 28 2 0 0 0 0 20 31 1 0 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.17
Volume:	441.663
LogP:	5.02
LogD:	3.215
LogS:	-4.024
# Rotatable Bonds:	7
TPSA:	107.97
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.292
Synthetic Accessibility Score:	3.366
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:	-4.863
MDCK Permeability:	1.4832246961304918e-05
Pgp-inhibitor:	0.334
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.087
30% Bioavailability (F30%):	0.917

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	98.44624328613281%
Volume Distribution (VD):	0.701
Pgp-substrate:	1.2922433614730835%

ADMET: Metabolism

CYP1A2-inhibitor:	0.382
CYP1A2-substrate:	0.476
CYP2C19-inhibitor:	0.311
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.807
CYP2C9-substrate:	0.836
CYP2D6-inhibitor:	0.052
CYP2D6-substrate:	0.232
CYP3A4-inhibitor:	0.124
CYP3A4-substrate:	0.139

ADMET: Excretion

Clearance (CL):	7.847
Half-life (T1/2):	0.162

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.767
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.294
Maximum Recommended Daily Dose:	0.63
Skin Sensitization:	0.296
Carcinogencity:	0.212
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.317

Download Data

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

Natural Product: NPC474735

Natural Product ID:	NPC474735
*Common Name:**	Disparinol A
IUPAC Name:	5,7-dihydroxy-8-(2-hydroxy-3-methylbut-3-enyl)-6-(3-methylbutanoyl)-4-phenylchromen-2-one
Synonyms:
Standard InCHIKey:	IQMQJKCHMGXLEU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H26O6/c1-13(2)10-19(27)22-23(29)17(11-18(26)14(3)4)25-21(24(22)30)16(12-20(28)31-25)15-8-6-5-7-9-15/h5-9,12-13,18,26,29-30H,3,10-11H2,1-2,4H3
SMILES:	CC(C)CC(=O)C1=C(C2=C(C(=C1O)CC(C(=C)C)O)OC(=O)C=C2C3=CC=CC=C3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480847
PubChem CID:	6483321
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
NPO33501	marila pluricostata	Species	Calophyllaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15787438]

☑ 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
GI50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	0.9	ug.mL-1	PMID[525727]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	0.6	ug.mL-1	PMID[525727]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	0.5	ug.mL-1	PMID[525727]

☑ 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 NPC474735 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	355
0.1-0.2	1445
0.2-0.3	3392
0.3-0.4	7617
0.4-0.5	11126
0.5-0.6	3966
0.6-0.7	5517
0.7-0.8	4866
0.8-0.85	2762
0.85-0.9	1345
0.9-0.95	259
0.95-1	47

Similarity Score	Similarity Level	Natural Product ID
0.9793	High Similarity	NPC290671
0.972	High Similarity	NPC470322
0.9655	High Similarity	NPC19238
0.965	High Similarity	NPC1886
0.965	High Similarity	NPC196137
0.9583	High Similarity	NPC154217
0.9583	High Similarity	NPC181388
0.958	High Similarity	NPC96216
0.958	High Similarity	NPC87609
0.958	High Similarity	NPC196459
0.958	High Similarity	NPC470296
0.958	High Similarity	NPC94794
0.958	High Similarity	NPC188632
0.958	High Similarity	NPC470909
0.958	High Similarity	NPC112791
0.958	High Similarity	NPC474939
0.953	High Similarity	NPC474609
0.953	High Similarity	NPC129053
0.953	High Similarity	NPC109967
0.953	High Similarity	NPC474738
0.953	High Similarity	NPC469936
0.953	High Similarity	NPC321372
0.953	High Similarity	NPC475797
0.953	High Similarity	NPC78554
0.9524	High Similarity	NPC312549
0.9524	High Similarity	NPC209142
0.9521	High Similarity	NPC104236
0.9521	High Similarity	NPC164205
0.9517	High Similarity	NPC285748
0.9514	High Similarity	NPC288910
0.9514	High Similarity	NPC133060
0.9514	High Similarity	NPC469935
0.9514	High Similarity	NPC224714
0.9514	High Similarity	NPC118059
0.9514	High Similarity	NPC470554
0.9514	High Similarity	NPC178627
0.951	High Similarity	NPC294432
0.951	High Similarity	NPC470556
0.951	High Similarity	NPC36181
0.9463	High Similarity	NPC279218
0.9463	High Similarity	NPC108937
0.9452	High Similarity	NPC208303
0.9452	High Similarity	NPC161864
0.9448	High Similarity	NPC472629
0.9448	High Similarity	NPC470910
0.9444	High Similarity	NPC307895
0.9444	High Similarity	NPC33653
0.9444	High Similarity	NPC184738
0.9444	High Similarity	NPC470553
0.9388	High Similarity	NPC469932
0.9388	High Similarity	NPC5173
0.9388	High Similarity	NPC470461
0.9384	High Similarity	NPC297886
0.9384	High Similarity	NPC474108
0.9384	High Similarity	NPC140120
0.9384	High Similarity	NPC177995
0.9384	High Similarity	NPC249942
0.9379	High Similarity	NPC124780
0.9379	High Similarity	NPC87486
0.9379	High Similarity	NPC470890
0.9379	High Similarity	NPC469953
0.9375	High Similarity	NPC112829
0.9324	High Similarity	NPC37348
0.9324	High Similarity	NPC61258
0.932	High Similarity	NPC470460
0.932	High Similarity	NPC469933
0.932	High Similarity	NPC168085
0.9315	High Similarity	NPC57470
0.9315	High Similarity	NPC476088
0.9315	High Similarity	NPC474161
0.931	High Similarity	NPC278249
0.931	High Similarity	NPC125894
0.931	High Similarity	NPC85162
0.931	High Similarity	NPC77794
0.931	High Similarity	NPC51887
0.931	High Similarity	NPC476178
0.931	High Similarity	NPC81697
0.931	High Similarity	NPC475705
0.931	High Similarity	NPC117836
0.931	High Similarity	NPC107177
0.931	High Similarity	NPC223812
0.9306	High Similarity	NPC110038
0.9306	High Similarity	NPC282300
0.9306	High Similarity	NPC248372
0.9301	High Similarity	NPC217186
0.9301	High Similarity	NPC53181
0.9301	High Similarity	NPC473209
0.9262	High Similarity	NPC316960
0.9262	High Similarity	NPC204561
0.9262	High Similarity	NPC78835
0.9262	High Similarity	NPC317715
0.9262	High Similarity	NPC309512
0.9262	High Similarity	NPC148945
0.9257	High Similarity	NPC317492
0.9252	High Similarity	NPC473077
0.9252	High Similarity	NPC296998
0.9252	High Similarity	NPC308200
0.9252	High Similarity	NPC180477
0.9247	High Similarity	NPC473014
0.9247	High Similarity	NPC473015
0.9247	High Similarity	NPC131568
0.9247	High Similarity	NPC216538
0.9247	High Similarity	NPC271288
0.9247	High Similarity	NPC273538
0.9247	High Similarity	NPC319752
0.9247	High Similarity	NPC326500
0.9247	High Similarity	NPC473013
0.9247	High Similarity	NPC235217
0.9247	High Similarity	NPC131579
0.9241	High Similarity	NPC306829
0.9241	High Similarity	NPC194432
0.9241	High Similarity	NPC265040
0.9241	High Similarity	NPC472344
0.9241	High Similarity	NPC76372
0.9241	High Similarity	NPC161506
0.9241	High Similarity	NPC148757
0.9241	High Similarity	NPC125855
0.9241	High Similarity	NPC296917
0.9241	High Similarity	NPC228504
0.9241	High Similarity	NPC10937
0.9241	High Similarity	NPC182852
0.9241	High Similarity	NPC78
0.9241	High Similarity	NPC66515
0.9241	High Similarity	NPC166482
0.9241	High Similarity	NPC220998
0.9241	High Similarity	NPC177354
0.9241	High Similarity	NPC167624
0.9241	High Similarity	NPC107572
0.9241	High Similarity	NPC227579
0.9241	High Similarity	NPC223500
0.9241	High Similarity	NPC324134
0.9241	High Similarity	NPC166934
0.9241	High Similarity	NPC1089
0.9241	High Similarity	NPC64915
0.9241	High Similarity	NPC37496
0.9241	High Similarity	NPC324436
0.9241	High Similarity	NPC40833
0.9241	High Similarity	NPC76338
0.9241	High Similarity	NPC32739
0.9241	High Similarity	NPC328164
0.9236	High Similarity	NPC241100
0.9236	High Similarity	NPC159275
0.9231	High Similarity	NPC183639
0.9231	High Similarity	NPC199458
0.9205	High Similarity	NPC469934
0.92	High Similarity	NPC217149
0.92	High Similarity	NPC56232
0.92	High Similarity	NPC256141
0.92	High Similarity	NPC161881
0.92	High Similarity	NPC244583
0.92	High Similarity	NPC216035
0.92	High Similarity	NPC150123
0.92	High Similarity	NPC10807
0.9195	High Similarity	NPC180351
0.9195	High Similarity	NPC476185
0.9195	High Similarity	NPC470908
0.9195	High Similarity	NPC472633
0.9195	High Similarity	NPC29777
0.9195	High Similarity	NPC471115
0.9195	High Similarity	NPC321896
0.9195	High Similarity	NPC105136
0.9189	High Similarity	NPC39195
0.9189	High Similarity	NPC145467
0.9189	High Similarity	NPC6511
0.9184	High Similarity	NPC24136
0.9184	High Similarity	NPC88964
0.9184	High Similarity	NPC187282
0.9184	High Similarity	NPC111786
0.9184	High Similarity	NPC178343
0.9184	High Similarity	NPC127059
0.9184	High Similarity	NPC195621
0.9184	High Similarity	NPC306488
0.9184	High Similarity	NPC301276
0.9184	High Similarity	NPC290133
0.9184	High Similarity	NPC285630
0.9184	High Similarity	NPC312973
0.9184	High Similarity	NPC267375
0.9184	High Similarity	NPC54577
0.9184	High Similarity	NPC475052
0.9184	High Similarity	NPC83357
0.9184	High Similarity	NPC470647
0.9184	High Similarity	NPC67805
0.9184	High Similarity	NPC176229
0.9184	High Similarity	NPC142405
0.9184	High Similarity	NPC5820
0.9184	High Similarity	NPC124729
0.9184	High Similarity	NPC246948
0.9184	High Similarity	NPC470458
0.9184	High Similarity	NPC20488
0.9184	High Similarity	NPC214774
0.9178	High Similarity	NPC175504
0.9178	High Similarity	NPC185276
0.9178	High Similarity	NPC149026
0.9178	High Similarity	NPC143896
0.9178	High Similarity	NPC316816
0.9178	High Similarity	NPC24821
0.9178	High Similarity	NPC150408
0.9178	High Similarity	NPC9117
0.9178	High Similarity	NPC91560
0.9178	High Similarity	NPC471621

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 NPC474735 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	897
0.2-0.3	1613
0.3-0.4	2507
0.4-0.5	2055
0.5-0.6	1131
0.6-0.7	413
0.7-0.8	138
0.8-0.85	50
0.85-0.9	23
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9247	High Similarity	NPD4378	Clinical (unspecified phase)
0.8961	High Similarity	NPD7075	Discontinued
0.8947	High Similarity	NPD6801	Discontinued
0.894	High Similarity	NPD4380	Phase 2
0.8897	High Similarity	NPD1550	Clinical (unspecified phase)
0.8897	High Similarity	NPD1552	Clinical (unspecified phase)
0.8889	High Similarity	NPD2393	Clinical (unspecified phase)
0.8889	High Similarity	NPD7096	Clinical (unspecified phase)
0.8882	High Similarity	NPD7411	Suspended
0.8859	High Similarity	NPD7410	Clinical (unspecified phase)
0.8836	High Similarity	NPD1549	Phase 2
0.8831	High Similarity	NPD8443	Clinical (unspecified phase)
0.8828	High Similarity	NPD2796	Approved
0.8766	High Similarity	NPD7819	Suspended
0.8759	High Similarity	NPD1510	Phase 2
0.8718	High Similarity	NPD4381	Clinical (unspecified phase)
0.8581	High Similarity	NPD1934	Approved
0.858	High Similarity	NPD7804	Clinical (unspecified phase)
0.8543	High Similarity	NPD6799	Approved
0.8535	High Similarity	NPD7768	Phase 2
0.8523	High Similarity	NPD7421	Clinical (unspecified phase)
0.8509	High Similarity	NPD7852	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD920	Approved
0.8483	Intermediate Similarity	NPD1240	Approved
0.8471	Intermediate Similarity	NPD3817	Phase 2
0.8467	Intermediate Similarity	NPD3750	Approved
0.8456	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1511	Approved
0.8408	Intermediate Similarity	NPD2801	Approved
0.84	Intermediate Similarity	NPD1243	Approved
0.8377	Intermediate Similarity	NPD5403	Approved
0.8367	Intermediate Similarity	NPD1607	Approved
0.8366	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD2533	Approved
0.8366	Intermediate Similarity	NPD2532	Approved
0.8366	Intermediate Similarity	NPD2534	Approved
0.8355	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD2313	Discontinued
0.8345	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6599	Discontinued
0.8323	Intermediate Similarity	NPD6959	Discontinued
0.8322	Intermediate Similarity	NPD2935	Discontinued
0.8322	Intermediate Similarity	NPD1551	Phase 2
0.8312	Intermediate Similarity	NPD1512	Approved
0.8299	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD5124	Phase 1
0.8293	Intermediate Similarity	NPD3818	Discontinued
0.8282	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6166	Phase 2
0.8278	Intermediate Similarity	NPD2800	Approved
0.8255	Intermediate Similarity	NPD2799	Discontinued
0.825	Intermediate Similarity	NPD3749	Approved
0.8247	Intermediate Similarity	NPD5401	Approved
0.8242	Intermediate Similarity	NPD5844	Phase 1
0.8242	Intermediate Similarity	NPD7054	Approved
0.8239	Intermediate Similarity	NPD5402	Approved
0.8232	Intermediate Similarity	NPD7473	Discontinued
0.8224	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD6559	Discontinued
0.8193	Intermediate Similarity	NPD7472	Approved
0.8193	Intermediate Similarity	NPD7074	Phase 3
0.8187	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD6232	Discontinued
0.8155	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD5494	Approved
0.8144	Intermediate Similarity	NPD5953	Discontinued
0.8144	Intermediate Similarity	NPD6797	Phase 2
0.8133	Intermediate Similarity	NPD7033	Discontinued
0.8133	Intermediate Similarity	NPD3748	Approved
0.8133	Intermediate Similarity	NPD7286	Phase 2
0.8121	Intermediate Similarity	NPD6651	Approved
0.8105	Intermediate Similarity	NPD4628	Phase 3
0.8095	Intermediate Similarity	NPD3268	Approved
0.8095	Intermediate Similarity	NPD7251	Discontinued
0.8075	Intermediate Similarity	NPD3882	Suspended
0.8047	Intermediate Similarity	NPD7808	Phase 3
0.8038	Intermediate Similarity	NPD3226	Approved
0.8	Intermediate Similarity	NPD2797	Approved
0.8	Intermediate Similarity	NPD1203	Approved
0.7975	Intermediate Similarity	NPD919	Approved
0.7959	Intermediate Similarity	NPD6832	Phase 2
0.7937	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD2346	Discontinued
0.7898	Intermediate Similarity	NPD4360	Phase 2
0.7898	Intermediate Similarity	NPD4363	Phase 3
0.7852	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD422	Phase 1
0.7824	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD9717	Approved
0.7785	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4308	Phase 3
0.7756	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD3267	Approved
0.7755	Intermediate Similarity	NPD3266	Approved
0.7725	Intermediate Similarity	NPD5710	Approved
0.7725	Intermediate Similarity	NPD5711	Approved
0.7718	Intermediate Similarity	NPD4908	Phase 1
0.7703	Intermediate Similarity	NPD2798	Approved
0.7702	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD3225	Approved
0.7677	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6004	Phase 3
0.7677	Intermediate Similarity	NPD6005	Phase 3
0.7677	Intermediate Similarity	NPD6002	Phase 3
0.7677	Intermediate Similarity	NPD2344	Approved
0.7677	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4361	Phase 2
0.7654	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1465	Phase 2
0.7619	Intermediate Similarity	NPD7229	Phase 3
0.7613	Intermediate Similarity	NPD6100	Approved
0.7613	Intermediate Similarity	NPD6099	Approved
0.7603	Intermediate Similarity	NPD1610	Phase 2
0.7603	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7458	Discontinued
0.7586	Intermediate Similarity	NPD8312	Approved
0.7586	Intermediate Similarity	NPD8313	Approved
0.7584	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1652	Phase 2
0.7569	Intermediate Similarity	NPD1548	Phase 1
0.756	Intermediate Similarity	NPD1247	Approved
0.7551	Intermediate Similarity	NPD1608	Approved
0.7548	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6273	Approved
0.7516	Intermediate Similarity	NPD4307	Phase 2
0.75	Intermediate Similarity	NPD1296	Phase 2
0.75	Intermediate Similarity	NPD5890	Approved
0.75	Intermediate Similarity	NPD5889	Approved
0.75	Intermediate Similarity	NPD6798	Discontinued
0.75	Intermediate Similarity	NPD7390	Discontinued
0.7484	Intermediate Similarity	NPD2309	Approved
0.747	Intermediate Similarity	NPD4288	Approved
0.7469	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD230	Phase 1
0.7468	Intermediate Similarity	NPD447	Suspended
0.7468	Intermediate Similarity	NPD6355	Discontinued
0.7467	Intermediate Similarity	NPD1019	Discontinued
0.7458	Intermediate Similarity	NPD8434	Phase 2
0.7456	Intermediate Similarity	NPD7199	Phase 2
0.7455	Intermediate Similarity	NPD37	Approved
0.7448	Intermediate Similarity	NPD9545	Approved
0.7433	Intermediate Similarity	NPD7584	Approved
0.7425	Intermediate Similarity	NPD4965	Approved
0.7425	Intermediate Similarity	NPD4967	Phase 2
0.7425	Intermediate Similarity	NPD4966	Approved
0.7421	Intermediate Similarity	NPD7003	Approved
0.741	Intermediate Similarity	NPD8455	Phase 2
0.7403	Intermediate Similarity	NPD943	Approved
0.7403	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1613	Approved
0.7389	Intermediate Similarity	NPD5406	Approved
0.7389	Intermediate Similarity	NPD5404	Approved
0.7389	Intermediate Similarity	NPD5405	Approved
0.7389	Intermediate Similarity	NPD5408	Approved
0.7386	Intermediate Similarity	NPD411	Approved
0.7374	Intermediate Similarity	NPD4287	Approved
0.7374	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1933	Approved
0.7347	Intermediate Similarity	NPD17	Approved
0.7341	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6233	Phase 2
0.7337	Intermediate Similarity	NPD6234	Discontinued
0.7333	Intermediate Similarity	NPD6585	Discontinued
0.7326	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1653	Approved
0.731	Intermediate Similarity	NPD9493	Approved
0.7302	Intermediate Similarity	NPD7585	Approved
0.729	Intermediate Similarity	NPD4060	Phase 1
0.7285	Intermediate Similarity	NPD1164	Approved
0.7284	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4476	Approved
0.7278	Intermediate Similarity	NPD4477	Approved
0.7273	Intermediate Similarity	NPD3764	Approved
0.7273	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3926	Phase 2
0.7267	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8150	Discontinued
0.7257	Intermediate Similarity	NPD1729	Discontinued
0.725	Intermediate Similarity	NPD2654	Approved
0.7249	Intermediate Similarity	NPD7583	Approved
0.7246	Intermediate Similarity	NPD6844	Discontinued
0.7241	Intermediate Similarity	NPD3751	Discontinued
0.7222	Intermediate Similarity	NPD6666	Approved
0.7222	Intermediate Similarity	NPD6667	Approved
0.7211	Intermediate Similarity	NPD1894	Discontinued
0.7209	Intermediate Similarity	NPD3787	Discontinued
0.7208	Intermediate Similarity	NPD4625	Phase 3
0.7208	Intermediate Similarity	NPD3027	Phase 3
0.7202	Intermediate Similarity	NPD5760	Phase 2
0.7202	Intermediate Similarity	NPD5761	Phase 2
0.72	Intermediate Similarity	NPD1481	Phase 2
0.7195	Intermediate Similarity	NPD5049	Phase 3
0.719	Intermediate Similarity	NPD2861	Phase 2
0.7188	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2424	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