NPASS Compound

Structure

NPC471114 OpenBabel07101719252D 31 33 0 0 1 0 0 0 0 0999 V2000 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 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 1.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 -3.3660 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 -4.3301 0.5000 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 1.7321 -1.0000 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 -1.7321 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 -5.1962 -0.0000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 3 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 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 3.4641 -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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 13 1 0 0 0 0 3 13 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 25 1 0 0 0 0 7 8 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 10 20 1 0 0 0 0 11 19 2 0 0 0 0 11 21 1 0 0 0 0 12 16 1 0 0 0 0 12 31 1 0 0 0 0 14 19 1 0 0 0 0 14 23 2 0 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 24 1 0 0 0 0 17 20 2 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 21 22 2 0 0 0 0 21 31 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 23 29 1 0 0 0 0 24 30 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.19
Volume:	444.3
LogP:	5.6
LogD:	3.396
LogS:	-3.662
# Rotatable Bonds:	5
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.512
Synthetic Accessibility Score:	3.853
Fsp3:	0.32
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:	-4.982
MDCK Permeability:	1.4734840988239739e-05
Pgp-inhibitor:	0.925
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.756

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	100.32132720947266%
Volume Distribution (VD):	0.557
Pgp-substrate:	0.8992506861686707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.629
CYP1A2-substrate:	0.771
CYP2C19-inhibitor:	0.736
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.853
CYP2C9-substrate:	0.867
CYP2D6-inhibitor:	0.901
CYP2D6-substrate:	0.53
CYP3A4-inhibitor:	0.447
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	3.7
Half-life (T1/2):	0.134

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.253
Drug-inuced Liver Injury (DILI):	0.277
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.341
Maximum Recommended Daily Dose:	0.437
Skin Sensitization:	0.933
Carcinogencity:	0.067
Eye Corrosion:	0.003
Eye Irritation:	0.897
Respiratory Toxicity:	0.084

Download Data

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

Natural Product: NPC471114

Natural Product ID:	NPC471114
*Common Name:**	Rac-3-[2,4-Dihydroxy-5-(2-Methylbut-3-En-2-Yl)Phenyl]-5,7-Dihydroxy-6-(3-Methylbut-2-En-1-Yl)Chroman-4-One
IUPAC Name:	3-[2,4-dihydroxy-5-(2-methylbut-3-en-2-yl)phenyl]-5,7-dihydroxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	LZKLWTGDIRDDIR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H28O6/c1-6-25(4,5)17-9-15(18(26)10-20(17)28)16-12-31-21-11-19(27)14(8-7-13(2)3)23(29)22(21)24(16)30/h6-7,9-11,16,26-29H,1,8,12H2,2-5H3
SMILES:	C=CC(c1cc(c(cc1O)O)C1COc2c(C1=O)c(O)c(c(c2)O)CC=C(C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375511
PubChem CID:	71713861
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones

*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
NPO33423	dalea formosa	Species	Fabaceae	Eukaryota	root	n.a.	n.a.	PMID[23631483]

☑ 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
MIC	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	244.0	ug.mL-1	PMID[484351]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	0.95	ug.mL-1	PMID[484351]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	15.2	ug.mL-1	PMID[484351]

☑ 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 NPC471114 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	382
0.1-0.2	1470
0.2-0.3	3284
0.3-0.4	7924
0.4-0.5	10694
0.5-0.6	3724
0.6-0.7	5333
0.7-0.8	5576
0.8-0.85	2352
0.85-0.9	1408
0.9-0.95	519
0.95-1	31

Similarity Score	Similarity Level	Natural Product ID
0.9859	High Similarity	NPC308200
0.979	High Similarity	NPC39195
0.979	High Similarity	NPC145467
0.972	High Similarity	NPC300988
0.972	High Similarity	NPC10990
0.9718	High Similarity	NPC311144
0.9718	High Similarity	NPC271288
0.9655	High Similarity	NPC471115
0.9655	High Similarity	NPC29777
0.965	High Similarity	NPC299011
0.9648	High Similarity	NPC113770
0.958	High Similarity	NPC184649
0.958	High Similarity	NPC303185
0.9527	High Similarity	NPC471116
0.9521	High Similarity	NPC476185
0.9521	High Similarity	NPC321896
0.9514	High Similarity	NPC477955
0.9514	High Similarity	NPC472629
0.951	High Similarity	NPC125894
0.951	High Similarity	NPC278249
0.951	High Similarity	NPC81697
0.951	High Similarity	NPC77794
0.951	High Similarity	NPC11700
0.951	High Similarity	NPC85162
0.951	High Similarity	NPC107177
0.951	High Similarity	NPC223812
0.9452	High Similarity	NPC473016
0.9444	High Similarity	NPC470890
0.9444	High Similarity	NPC473014
0.9444	High Similarity	NPC476055
0.9444	High Similarity	NPC473013
0.9444	High Similarity	NPC235217
0.9444	High Similarity	NPC87486
0.9444	High Similarity	NPC131568
0.9444	High Similarity	NPC131579
0.9444	High Similarity	NPC473015
0.9444	High Similarity	NPC124780
0.9441	High Similarity	NPC66515
0.9441	High Similarity	NPC202981
0.9441	High Similarity	NPC306829
0.9441	High Similarity	NPC32739
0.9441	High Similarity	NPC76372
0.9441	High Similarity	NPC194432
0.9441	High Similarity	NPC107572
0.9441	High Similarity	NPC324134
0.9441	High Similarity	NPC296917
0.9441	High Similarity	NPC166934
0.9441	High Similarity	NPC324436
0.9441	High Similarity	NPC161506
0.9441	High Similarity	NPC37496
0.9441	High Similarity	NPC167624
0.9441	High Similarity	NPC228504
0.9441	High Similarity	NPC227579
0.9441	High Similarity	NPC220998
0.9441	High Similarity	NPC76338
0.9441	High Similarity	NPC64915
0.9441	High Similarity	NPC78
0.9441	High Similarity	NPC166482
0.9441	High Similarity	NPC223500
0.9441	High Similarity	NPC177354
0.9441	High Similarity	NPC10937
0.9441	High Similarity	NPC265040
0.9441	High Similarity	NPC40833
0.9441	High Similarity	NPC328164
0.9441	High Similarity	NPC182852
0.9441	High Similarity	NPC1089
0.9441	High Similarity	NPC125855
0.9441	High Similarity	NPC148757
0.9437	High Similarity	NPC76445
0.9437	High Similarity	NPC129853
0.9437	High Similarity	NPC284550
0.9392	High Similarity	NPC210597
0.9379	High Similarity	NPC127059
0.9379	High Similarity	NPC24136
0.9379	High Similarity	NPC187282
0.9379	High Similarity	NPC290133
0.9379	High Similarity	NPC285630
0.9375	High Similarity	NPC149026
0.9375	High Similarity	NPC310130
0.9375	High Similarity	NPC478086
0.9375	High Similarity	NPC106985
0.9375	High Similarity	NPC150408
0.9375	High Similarity	NPC68104
0.9375	High Similarity	NPC164980
0.9375	High Similarity	NPC166138
0.9375	High Similarity	NPC75049
0.9375	High Similarity	NPC185276
0.9375	High Similarity	NPC316816
0.9375	High Similarity	NPC214166
0.9375	High Similarity	NPC18585
0.9375	High Similarity	NPC91560
0.9375	High Similarity	NPC169591
0.9375	High Similarity	NPC143896
0.9375	High Similarity	NPC257097
0.9375	High Similarity	NPC39329
0.9375	High Similarity	NPC175504
0.9375	High Similarity	NPC221432
0.9371	High Similarity	NPC96408
0.9371	High Similarity	NPC248372
0.9371	High Similarity	NPC4743
0.9371	High Similarity	NPC156190
0.9371	High Similarity	NPC279650
0.9371	High Similarity	NPC312391
0.9371	High Similarity	NPC213322
0.9371	High Similarity	NPC110038
0.9371	High Similarity	NPC258630
0.9371	High Similarity	NPC166689
0.9371	High Similarity	NPC17170
0.9371	High Similarity	NPC282300
0.9371	High Similarity	NPC3188
0.9371	High Similarity	NPC324386
0.9366	High Similarity	NPC316480
0.9329	High Similarity	NPC209760
0.9329	High Similarity	NPC213608
0.9329	High Similarity	NPC1477
0.9329	High Similarity	NPC100134
0.9324	High Similarity	NPC470675
0.9324	High Similarity	NPC473131
0.9324	High Similarity	NPC178484
0.9324	High Similarity	NPC305965
0.932	High Similarity	NPC317492
0.932	High Similarity	NPC266499
0.932	High Similarity	NPC470461
0.9315	High Similarity	NPC296998
0.9315	High Similarity	NPC473077
0.931	High Similarity	NPC326500
0.931	High Similarity	NPC470673
0.931	High Similarity	NPC209040
0.931	High Similarity	NPC224714
0.931	High Similarity	NPC470674
0.931	High Similarity	NPC234629
0.931	High Similarity	NPC216538
0.931	High Similarity	NPC117716
0.931	High Similarity	NPC311741
0.931	High Similarity	NPC273538
0.931	High Similarity	NPC236766
0.931	High Similarity	NPC197252
0.9306	High Similarity	NPC144499
0.9301	High Similarity	NPC159275
0.9301	High Similarity	NPC110228
0.9301	High Similarity	NPC69769
0.9301	High Similarity	NPC11056
0.9301	High Similarity	NPC6407
0.9301	High Similarity	NPC241100
0.9301	High Similarity	NPC188243
0.9296	High Similarity	NPC118813
0.9272	High Similarity	NPC196448
0.9267	High Similarity	NPC476169
0.9262	High Similarity	NPC216035
0.9262	High Similarity	NPC5871
0.9262	High Similarity	NPC217149
0.9257	High Similarity	NPC188403
0.9257	High Similarity	NPC227122
0.9257	High Similarity	NPC472633
0.9252	High Similarity	NPC186397
0.9252	High Similarity	NPC266572
0.9252	High Similarity	NPC168085
0.9252	High Similarity	NPC470460
0.9252	High Similarity	NPC37135
0.9252	High Similarity	NPC296869
0.9247	High Similarity	NPC5820
0.9247	High Similarity	NPC124729
0.9247	High Similarity	NPC470131
0.9247	High Similarity	NPC306488
0.9247	High Similarity	NPC214774
0.9247	High Similarity	NPC67805
0.9247	High Similarity	NPC476088
0.9247	High Similarity	NPC470132
0.9247	High Similarity	NPC312973
0.9247	High Similarity	NPC301276
0.9247	High Similarity	NPC142405
0.9247	High Similarity	NPC83357
0.9247	High Similarity	NPC178343
0.9247	High Similarity	NPC474161
0.9247	High Similarity	NPC176229
0.9247	High Similarity	NPC246948
0.9247	High Similarity	NPC54577
0.9247	High Similarity	NPC267375
0.9247	High Similarity	NPC20488
0.9247	High Similarity	NPC88964
0.9247	High Similarity	NPC470133
0.9247	High Similarity	NPC470647
0.9247	High Similarity	NPC109183
0.9247	High Similarity	NPC470134
0.9247	High Similarity	NPC475052
0.9247	High Similarity	NPC111786
0.9247	High Similarity	NPC473078
0.9247	High Similarity	NPC195621
0.9241	High Similarity	NPC24821
0.9241	High Similarity	NPC219915
0.9241	High Similarity	NPC9117
0.9241	High Similarity	NPC212932
0.9241	High Similarity	NPC190637
0.9241	High Similarity	NPC293053
0.9236	High Similarity	NPC52789
0.9236	High Similarity	NPC268204
0.9236	High Similarity	NPC110969
0.9236	High Similarity	NPC469404
0.9236	High Similarity	NPC26051
0.9236	High Similarity	NPC55832

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 NPC471114 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	925
0.2-0.3	1505
0.3-0.4	2503
0.4-0.5	1994
0.5-0.6	1141
0.6-0.7	519
0.7-0.8	153
0.8-0.85	45
0.85-0.9	20
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.931	High Similarity	NPD4378	Clinical (unspecified phase)
0.9139	High Similarity	NPD8443	Clinical (unspecified phase)
0.9091	High Similarity	NPD1552	Clinical (unspecified phase)
0.9091	High Similarity	NPD1550	Clinical (unspecified phase)
0.9073	High Similarity	NPD2393	Clinical (unspecified phase)
0.9028	High Similarity	NPD1549	Phase 2
0.8874	High Similarity	NPD4380	Phase 2
0.8836	High Similarity	NPD2800	Approved
0.8824	High Similarity	NPD7819	Suspended
0.8819	High Similarity	NPD1510	Phase 2
0.8816	High Similarity	NPD7411	Suspended
0.8792	High Similarity	NPD7410	Clinical (unspecified phase)
0.8774	High Similarity	NPD7075	Discontinued
0.8759	High Similarity	NPD2796	Approved
0.8758	High Similarity	NPD1934	Approved
0.8701	High Similarity	NPD7096	Clinical (unspecified phase)
0.8671	High Similarity	NPD1240	Approved
0.8608	High Similarity	NPD6959	Discontinued
0.8581	High Similarity	NPD2801	Approved
0.8562	High Similarity	NPD7852	Clinical (unspecified phase)
0.8552	High Similarity	NPD1607	Approved
0.8544	High Similarity	NPD5494	Approved
0.8535	High Similarity	NPD4381	Clinical (unspecified phase)
0.8506	High Similarity	NPD6599	Discontinued
0.8477	Intermediate Similarity	NPD1511	Approved
0.8471	Intermediate Similarity	NPD7768	Phase 2
0.8425	Intermediate Similarity	NPD6651	Approved
0.8405	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD6801	Discontinued
0.8366	Intermediate Similarity	NPD1512	Approved
0.8355	Intermediate Similarity	NPD6799	Approved
0.8354	Intermediate Similarity	NPD3882	Suspended
0.8333	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6166	Phase 2
0.8311	Intermediate Similarity	NPD2799	Discontinued
0.8302	Intermediate Similarity	NPD3749	Approved
0.8301	Intermediate Similarity	NPD2534	Approved
0.8301	Intermediate Similarity	NPD2532	Approved
0.8301	Intermediate Similarity	NPD2533	Approved
0.8282	Intermediate Similarity	NPD7473	Discontinued
0.8278	Intermediate Similarity	NPD3750	Approved
0.8276	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD6099	Approved
0.8255	Intermediate Similarity	NPD6100	Approved
0.821	Intermediate Similarity	NPD6232	Discontinued
0.8204	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD920	Approved
0.8176	Intermediate Similarity	NPD3817	Phase 2
0.8151	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD4908	Phase 1
0.8133	Intermediate Similarity	NPD2935	Discontinued
0.8133	Intermediate Similarity	NPD7074	Phase 3
0.8133	Intermediate Similarity	NPD1551	Phase 2
0.8125	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD3818	Discontinued
0.8084	Intermediate Similarity	NPD5953	Discontinued
0.8079	Intermediate Similarity	NPD2344	Approved
0.8072	Intermediate Similarity	NPD7054	Approved
0.8072	Intermediate Similarity	NPD7286	Phase 2
0.8065	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD4628	Phase 3
0.8039	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD6559	Discontinued
0.8028	Intermediate Similarity	NPD1610	Phase 2
0.8027	Intermediate Similarity	NPD2313	Discontinued
0.8024	Intermediate Similarity	NPD7472	Approved
0.7976	Intermediate Similarity	NPD6797	Phase 2
0.7975	Intermediate Similarity	NPD3226	Approved
0.7974	Intermediate Similarity	NPD1243	Approved
0.7964	Intermediate Similarity	NPD5844	Phase 1
0.7961	Intermediate Similarity	NPD2346	Discontinued
0.7947	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD3748	Approved
0.7943	Intermediate Similarity	NPD4360	Phase 2
0.7943	Intermediate Similarity	NPD4363	Phase 3
0.7935	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD7251	Discontinued
0.7922	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7808	Phase 3
0.7882	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD2309	Approved
0.7848	Intermediate Similarity	NPD5403	Approved
0.784	Intermediate Similarity	NPD5402	Approved
0.7834	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD3268	Approved
0.7778	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5710	Approved
0.7771	Intermediate Similarity	NPD5711	Approved
0.7771	Intermediate Similarity	NPD7390	Discontinued
0.7755	Intermediate Similarity	NPD2798	Approved
0.775	Intermediate Similarity	NPD7458	Discontinued
0.7722	Intermediate Similarity	NPD5401	Approved
0.7711	Intermediate Similarity	NPD1247	Approved
0.7697	Intermediate Similarity	NPD4361	Phase 2
0.7697	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1203	Approved
0.7687	Intermediate Similarity	NPD2797	Approved
0.7682	Intermediate Similarity	NPD943	Approved
0.7669	Intermediate Similarity	NPD1465	Phase 2
0.7667	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7229	Phase 3
0.7661	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6832	Phase 2
0.7632	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5124	Phase 1
0.7622	Intermediate Similarity	NPD1548	Phase 1
0.7619	Intermediate Similarity	NPD3926	Phase 2
0.7613	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD3972	Approved
0.76	Intermediate Similarity	NPD4625	Phase 3
0.7597	Intermediate Similarity	NPD7033	Discontinued
0.759	Intermediate Similarity	NPD919	Approved
0.758	Intermediate Similarity	NPD7003	Approved
0.7561	Intermediate Similarity	NPD5760	Phase 2
0.7561	Intermediate Similarity	NPD5761	Phase 2
0.7531	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8313	Approved
0.7529	Intermediate Similarity	NPD8312	Approved
0.7528	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8434	Phase 2
0.7483	Intermediate Similarity	NPD9717	Approved
0.7483	Intermediate Similarity	NPD1608	Approved
0.7467	Intermediate Similarity	NPD2861	Phase 2
0.7451	Intermediate Similarity	NPD1613	Approved
0.7451	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3267	Approved
0.745	Intermediate Similarity	NPD3266	Approved
0.7432	Intermediate Similarity	NPD4749	Approved
0.7417	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD422	Phase 1
0.7414	Intermediate Similarity	NPD6104	Discontinued
0.7405	Intermediate Similarity	NPD2654	Approved
0.7403	Intermediate Similarity	NPD230	Phase 1
0.7403	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD1729	Discontinued
0.7384	Intermediate Similarity	NPD3751	Discontinued
0.7372	Intermediate Similarity	NPD4308	Phase 3
0.7368	Intermediate Similarity	NPD2403	Approved
0.7363	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3787	Discontinued
0.7351	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6273	Approved
0.7342	Intermediate Similarity	NPD2424	Discontinued
0.7333	Intermediate Similarity	NPD1470	Approved
0.732	Intermediate Similarity	NPD3764	Approved
0.7318	Intermediate Similarity	NPD4287	Approved
0.7305	Intermediate Similarity	NPD4288	Approved
0.7305	Intermediate Similarity	NPD2296	Approved
0.7301	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1201	Approved
0.7294	Intermediate Similarity	NPD7199	Phase 2
0.729	Intermediate Similarity	NPD447	Suspended
0.729	Intermediate Similarity	NPD6355	Discontinued
0.729	Intermediate Similarity	NPD1933	Approved
0.7289	Intermediate Similarity	NPD6844	Discontinued
0.7289	Intermediate Similarity	NPD37	Approved
0.7287	Intermediate Similarity	NPD7584	Approved
0.7283	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD17	Approved
0.7278	Intermediate Similarity	NPD6002	Phase 3
0.7278	Intermediate Similarity	NPD6004	Phase 3
0.7278	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1471	Phase 3
0.7278	Intermediate Similarity	NPD6234	Discontinued
0.7278	Intermediate Similarity	NPD6005	Phase 3
0.7267	Intermediate Similarity	NPD3225	Approved
0.7262	Intermediate Similarity	NPD4965	Approved
0.7262	Intermediate Similarity	NPD4967	Phase 2
0.7262	Intermediate Similarity	NPD4966	Approved
0.7261	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD9545	Approved
0.7246	Intermediate Similarity	NPD8455	Phase 2
0.7243	Intermediate Similarity	NPD6776	Approved
0.7243	Intermediate Similarity	NPD6782	Approved
0.7243	Intermediate Similarity	NPD6780	Approved
0.7243	Intermediate Similarity	NPD6778	Approved
0.7243	Intermediate Similarity	NPD6777	Approved
0.7243	Intermediate Similarity	NPD6781	Approved
0.7243	Intermediate Similarity	NPD6779	Approved
0.7229	Intermediate Similarity	NPD5890	Approved
0.7229	Intermediate Similarity	NPD5889	Approved
0.7226	Intermediate Similarity	NPD4060	Phase 1
0.7222	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1164	Approved
0.7216	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5408	Approved
0.7215	Intermediate Similarity	NPD4476	Approved
0.7215	Intermediate Similarity	NPD4477	Approved
0.7215	Intermediate Similarity	NPD5404	Approved
0.7215	Intermediate Similarity	NPD5405	Approved
0.7215	Intermediate Similarity	NPD5406	Approved
0.7211	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6798	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