NPASS Compound

Structure

CID160821 OpenBabel06191715532D 34 37 0 0 1 0 0 0 0 0999 V2000 9.5263 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 6.0000 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 6.0622 -1.5000 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 -1.3660 -0.3660 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 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 3.5000 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 6.0622 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 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 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 8.6603 5.0000 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 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 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 3.0000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 19 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 18 2 0 0 0 0 8 11 1 0 0 0 0 8 19 2 0 0 0 0 9 22 1 0 0 0 0 10 12 2 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 12 26 1 0 0 0 0 13 14 2 0 0 0 0 13 21 1 0 0 0 0 14 30 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 22 2 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 17 27 1 0 0 0 0 21 26 2 0 0 0 0 22 28 1 0 0 0 0 23 28 2 0 0 0 0 23 29 1 0 0 0 0 24 25 1 0 0 0 0 24 29 2 0 0 0 0 25 31 2 0 0 0 0 26 34 1 0 0 0 0 27 20 1 6 0 0 0 27 33 1 0 0 0 0 28 32 1 0 0 0 0 29 33 1 0 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.25
Volume:	502.006
LogP:	8.16
LogD:	5.039
LogS:	-3.835
# Rotatable Bonds:	5
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	3.816
Fsp3:	0.367
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.707
MDCK Permeability:	2.1446905520861037e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.191
30% Bioavailability (F30%):	0.031

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	90.92738342285156%
Volume Distribution (VD):	3.48
Pgp-substrate:	10.753355979919434%

ADMET: Metabolism

CYP1A2-inhibitor:	0.162
CYP1A2-substrate:	0.412
CYP2C19-inhibitor:	0.937
CYP2C19-substrate:	0.161
CYP2C9-inhibitor:	0.942
CYP2C9-substrate:	0.949
CYP2D6-inhibitor:	0.748
CYP2D6-substrate:	0.532
CYP3A4-inhibitor:	0.671
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	13.315
Half-life (T1/2):	0.026

ADMET: Toxicity

hERG Blockers:	0.616
Human Hepatotoxicity (H-HT):	0.979
Drug-inuced Liver Injury (DILI):	0.402
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.73
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.558
Carcinogencity:	0.451
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC160821

Natural Product ID:	NPC160821
*Common Name:**	Lespeflorin A3
IUPAC Name:	(2S)-2-(2,2-dimethylchromen-6-yl)-7-hydroxy-6,8-bis(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Synonyms:	Lespeflorin A3
Standard InCHIKey:	SAZBMMMZQLNWMN-MHZLTWQESA-N
Standard InCHI:	InChI=1S/C30H34O4/c1-18(2)7-9-22-16-24-25(31)17-27(33-29(24)23(28(22)32)11-8-19(3)4)20-10-12-26-21(15-20)13-14-30(5,6)34-26/h7-8,10,12-16,27,32H,9,11,17H2,1-6H3/t27-/m0/s1
SMILES:	CC(=CCc1cc2C(=O)C[C@@H](c3ccc4c(C=CC(C)(C)O4)c3)Oc2c(CC=C(C)C)c1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL550552
PubChem CID:	25243166
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003642] 8-prenylated flavans [CHEMONTID:0003508] 8-prenylated flavanones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	1500.0	nM	PMID[512881]

☑ 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 NPC160821 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	373
0.1-0.2	1498
0.2-0.3	3611
0.3-0.4	9637
0.4-0.5	9014
0.5-0.6	3622
0.6-0.7	5985
0.7-0.8	5291
0.8-0.85	2087
0.85-0.9	1028
0.9-0.95	429
0.95-1	122

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC132592
0.9929	High Similarity	NPC110303
0.9929	High Similarity	NPC23728
0.9929	High Similarity	NPC283234
0.9858	High Similarity	NPC195621
0.9858	High Similarity	NPC111786
0.9858	High Similarity	NPC176229
0.9858	High Similarity	NPC20488
0.9858	High Similarity	NPC475052
0.9858	High Similarity	NPC214774
0.9858	High Similarity	NPC267375
0.9858	High Similarity	NPC246948
0.9858	High Similarity	NPC88964
0.9858	High Similarity	NPC312973
0.9858	High Similarity	NPC470647
0.9858	High Similarity	NPC54577
0.9858	High Similarity	NPC67805
0.9858	High Similarity	NPC83357
0.9858	High Similarity	NPC301276
0.9858	High Similarity	NPC142405
0.9789	High Similarity	NPC296998
0.9789	High Similarity	NPC473077
0.9787	High Similarity	NPC209040
0.9787	High Similarity	NPC197252
0.9787	High Similarity	NPC236766
0.972	High Similarity	NPC161191
0.9718	High Similarity	NPC127059
0.9718	High Similarity	NPC285630
0.9716	High Similarity	NPC310130
0.9716	High Similarity	NPC164980
0.9716	High Similarity	NPC221432
0.9716	High Similarity	NPC91560
0.9716	High Similarity	NPC185276
0.9716	High Similarity	NPC150408
0.9716	High Similarity	NPC68104
0.9716	High Similarity	NPC149026
0.9716	High Similarity	NPC257097
0.9716	High Similarity	NPC75049
0.9716	High Similarity	NPC214166
0.9716	High Similarity	NPC169591
0.9716	High Similarity	NPC143896
0.9716	High Similarity	NPC39329
0.9716	High Similarity	NPC316816
0.9716	High Similarity	NPC478086
0.9716	High Similarity	NPC38219
0.9716	High Similarity	NPC175504
0.965	High Similarity	NPC24673
0.965	High Similarity	NPC201731
0.965	High Similarity	NPC104406
0.965	High Similarity	NPC97716
0.965	High Similarity	NPC237635
0.965	High Similarity	NPC79469
0.9648	High Similarity	NPC473013
0.9648	High Similarity	NPC473014
0.9648	High Similarity	NPC131579
0.9648	High Similarity	NPC131568
0.9648	High Similarity	NPC319752
0.9648	High Similarity	NPC235217
0.9648	High Similarity	NPC473015
0.9645	High Similarity	NPC37496
0.9645	High Similarity	NPC10937
0.9645	High Similarity	NPC226636
0.9645	High Similarity	NPC324436
0.9645	High Similarity	NPC228504
0.9645	High Similarity	NPC182852
0.9645	High Similarity	NPC227579
0.9645	High Similarity	NPC1089
0.9645	High Similarity	NPC265040
0.9645	High Similarity	NPC223500
0.9645	High Similarity	NPC161506
0.9645	High Similarity	NPC40833
0.9645	High Similarity	NPC296917
0.9645	High Similarity	NPC32739
0.9645	High Similarity	NPC64915
0.9645	High Similarity	NPC78
0.9645	High Similarity	NPC66515
0.9645	High Similarity	NPC166482
0.9645	High Similarity	NPC76372
0.9645	High Similarity	NPC324134
0.9645	High Similarity	NPC148757
0.9645	High Similarity	NPC107572
0.9645	High Similarity	NPC306829
0.9645	High Similarity	NPC11561
0.9645	High Similarity	NPC194432
0.9645	High Similarity	NPC328164
0.9645	High Similarity	NPC147145
0.9645	High Similarity	NPC166934
0.9645	High Similarity	NPC177354
0.9645	High Similarity	NPC76338
0.9645	High Similarity	NPC125855
0.9645	High Similarity	NPC167624
0.9645	High Similarity	NPC220998
0.9586	High Similarity	NPC188403
0.9586	High Similarity	NPC472633
0.9583	High Similarity	NPC189087
0.9583	High Similarity	NPC6511
0.9583	High Similarity	NPC321623
0.9583	High Similarity	NPC266572
0.958	High Similarity	NPC474161
0.958	High Similarity	NPC109183
0.958	High Similarity	NPC470132
0.958	High Similarity	NPC476088
0.958	High Similarity	NPC470131
0.958	High Similarity	NPC473078
0.958	High Similarity	NPC470133
0.958	High Similarity	NPC470134
0.9577	High Similarity	NPC81697
0.9577	High Similarity	NPC106985
0.9577	High Similarity	NPC18585
0.9577	High Similarity	NPC85162
0.9577	High Similarity	NPC278249
0.9577	High Similarity	NPC223812
0.9577	High Similarity	NPC125894
0.9577	High Similarity	NPC107177
0.9577	High Similarity	NPC166138
0.9577	High Similarity	NPC77794
0.9577	High Similarity	NPC219915
0.9574	High Similarity	NPC96408
0.9574	High Similarity	NPC4743
0.9574	High Similarity	NPC156190
0.9574	High Similarity	NPC3188
0.9574	High Similarity	NPC279650
0.9574	High Similarity	NPC324386
0.9574	High Similarity	NPC312391
0.9574	High Similarity	NPC205006
0.9574	High Similarity	NPC248372
0.9574	High Similarity	NPC213322
0.9574	High Similarity	NPC258630
0.9574	High Similarity	NPC103362
0.9574	High Similarity	NPC156590
0.9574	High Similarity	NPC166689
0.9574	High Similarity	NPC118840
0.9574	High Similarity	NPC64908
0.9574	High Similarity	NPC110969
0.9574	High Similarity	NPC110038
0.9574	High Similarity	NPC147688
0.9574	High Similarity	NPC17170
0.9524	High Similarity	NPC223701
0.9524	High Similarity	NPC472583
0.9524	High Similarity	NPC7989
0.9517	High Similarity	NPC164205
0.9517	High Similarity	NPC5173
0.9517	High Similarity	NPC473016
0.9517	High Similarity	NPC104236
0.9517	High Similarity	NPC472628
0.9514	High Similarity	NPC472627
0.951	High Similarity	NPC39045
0.951	High Similarity	NPC470136
0.951	High Similarity	NPC311741
0.951	High Similarity	NPC234629
0.951	High Similarity	NPC470135
0.9507	High Similarity	NPC62840
0.9507	High Similarity	NPC217083
0.9507	High Similarity	NPC59739
0.9507	High Similarity	NPC299080
0.9507	High Similarity	NPC144499
0.9507	High Similarity	NPC78803
0.9507	High Similarity	NPC293852
0.9507	High Similarity	NPC214236
0.9504	High Similarity	NPC471587
0.9504	High Similarity	NPC69769
0.9504	High Similarity	NPC110228
0.9504	High Similarity	NPC261227
0.9504	High Similarity	NPC475680
0.9504	High Similarity	NPC241100
0.9504	High Similarity	NPC270883
0.9504	High Similarity	NPC6407
0.9504	High Similarity	NPC172986
0.9504	High Similarity	NPC188243
0.9504	High Similarity	NPC159275
0.9504	High Similarity	NPC305355
0.9504	High Similarity	NPC472409
0.9504	High Similarity	NPC150522
0.9504	High Similarity	NPC235239
0.9459	High Similarity	NPC477958
0.9456	High Similarity	NPC477957
0.9452	High Similarity	NPC471115
0.9452	High Similarity	NPC29777
0.9452	High Similarity	NPC61258
0.9448	High Similarity	NPC296869
0.9448	High Similarity	NPC168085
0.9444	High Similarity	NPC477955
0.9444	High Similarity	NPC228779
0.9444	High Similarity	NPC472629
0.9441	High Similarity	NPC59522
0.9437	High Similarity	NPC282300
0.9433	High Similarity	NPC140890
0.9433	High Similarity	NPC18260
0.9433	High Similarity	NPC23257
0.9433	High Similarity	NPC11566
0.9433	High Similarity	NPC265871
0.9433	High Similarity	NPC150648
0.9433	High Similarity	NPC274784
0.9433	High Similarity	NPC96565
0.9433	High Similarity	NPC329203
0.9433	High Similarity	NPC220062
0.9433	High Similarity	NPC222342
0.9433	High Similarity	NPC78913
0.9433	High Similarity	NPC53181
0.9433	High Similarity	NPC55018

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 NPC160821 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	940
0.2-0.3	1510
0.3-0.4	2565
0.4-0.5	1982
0.5-0.6	1185
0.6-0.7	434
0.7-0.8	165
0.8-0.85	29
0.85-0.9	12
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9375	High Similarity	NPD7410	Clinical (unspecified phase)
0.9362	High Similarity	NPD1549	Phase 2
0.9291	High Similarity	NPD1550	Clinical (unspecified phase)
0.9291	High Similarity	NPD1552	Clinical (unspecified phase)
0.9241	High Similarity	NPD4378	Clinical (unspecified phase)
0.92	High Similarity	NPD8443	Clinical (unspecified phase)
0.9189	High Similarity	NPD4380	Phase 2
0.9128	High Similarity	NPD7411	Suspended
0.9085	High Similarity	NPD2796	Approved
0.9079	High Similarity	NPD7075	Discontinued
0.9014	High Similarity	NPD1510	Phase 2
0.9007	High Similarity	NPD2393	Clinical (unspecified phase)
0.9007	High Similarity	NPD7096	Clinical (unspecified phase)
0.8882	High Similarity	NPD7819	Suspended
0.8865	High Similarity	NPD1240	Approved
0.8831	High Similarity	NPD4381	Clinical (unspecified phase)
0.8816	High Similarity	NPD6801	Discontinued
0.8741	High Similarity	NPD1607	Approved
0.8693	High Similarity	NPD1934	Approved
0.8688	High Similarity	NPD7804	Clinical (unspecified phase)
0.8645	High Similarity	NPD7768	Phase 2
0.8616	High Similarity	NPD7852	Clinical (unspecified phase)
0.8544	High Similarity	NPD6959	Discontinued
0.8533	High Similarity	NPD6799	Approved
0.8514	High Similarity	NPD7421	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD3750	Approved
0.8411	Intermediate Similarity	NPD1511	Approved
0.8397	Intermediate Similarity	NPD2801	Approved
0.8385	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD6166	Phase 2
0.8385	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD5403	Approved
0.8365	Intermediate Similarity	NPD5494	Approved
0.8354	Intermediate Similarity	NPD3749	Approved
0.8344	Intermediate Similarity	NPD7054	Approved
0.8333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6599	Discontinued
0.8301	Intermediate Similarity	NPD1512	Approved
0.8293	Intermediate Similarity	NPD7472	Approved
0.8293	Intermediate Similarity	NPD7074	Phase 3
0.8291	Intermediate Similarity	NPD3882	Suspended
0.8235	Intermediate Similarity	NPD5401	Approved
0.8231	Intermediate Similarity	NPD6651	Approved
0.8193	Intermediate Similarity	NPD7251	Discontinued
0.8188	Intermediate Similarity	NPD1551	Phase 2
0.8176	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD3818	Discontinued
0.8146	Intermediate Similarity	NPD2800	Approved
0.8146	Intermediate Similarity	NPD1243	Approved
0.8144	Intermediate Similarity	NPD7808	Phase 3
0.8133	Intermediate Similarity	NPD6797	Phase 2
0.8129	Intermediate Similarity	NPD920	Approved
0.8121	Intermediate Similarity	NPD3748	Approved
0.8121	Intermediate Similarity	NPD7286	Phase 2
0.8113	Intermediate Similarity	NPD3817	Phase 2
0.8105	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD6559	Discontinued
0.8082	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD2935	Discontinued
0.8041	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD5124	Phase 1
0.8036	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD5953	Discontinued
0.8012	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7033	Discontinued
0.8	Intermediate Similarity	NPD2799	Discontinued
0.8	Intermediate Similarity	NPD5402	Approved
0.7974	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD2313	Discontinued
0.7947	Intermediate Similarity	NPD6100	Approved
0.7947	Intermediate Similarity	NPD6099	Approved
0.7945	Intermediate Similarity	NPD6832	Phase 2
0.7945	Intermediate Similarity	NPD4908	Phase 1
0.7929	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD2344	Approved
0.7892	Intermediate Similarity	NPD7473	Discontinued
0.7886	Intermediate Similarity	NPD4363	Phase 3
0.7886	Intermediate Similarity	NPD4360	Phase 2
0.7885	Intermediate Similarity	NPD2532	Approved
0.7885	Intermediate Similarity	NPD2534	Approved
0.7885	Intermediate Similarity	NPD2533	Approved
0.7862	Intermediate Similarity	NPD1203	Approved
0.7857	Intermediate Similarity	NPD4628	Phase 3
0.7857	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6232	Discontinued
0.7812	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1548	Phase 1
0.7763	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD919	Approved
0.7718	Intermediate Similarity	NPD3268	Approved
0.7708	Intermediate Similarity	NPD1610	Phase 2
0.7706	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD7584	Approved
0.7692	Intermediate Similarity	NPD2309	Approved
0.7688	Intermediate Similarity	NPD3226	Approved
0.7687	Intermediate Similarity	NPD2798	Approved
0.767	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2346	Discontinued
0.7655	Intermediate Similarity	NPD9717	Approved
0.7651	Intermediate Similarity	NPD1247	Approved
0.7647	Intermediate Similarity	NPD4308	Phase 3
0.7619	Intermediate Similarity	NPD2797	Approved
0.7616	Intermediate Similarity	NPD943	Approved
0.7595	Intermediate Similarity	NPD7390	Discontinued
0.7593	Intermediate Similarity	NPD5890	Approved
0.7593	Intermediate Similarity	NPD5889	Approved
0.7586	Intermediate Similarity	NPD422	Phase 1
0.7578	Intermediate Similarity	NPD7458	Discontinued
0.7578	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD3225	Approved
0.7547	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6844	Discontinued
0.7544	Intermediate Similarity	NPD1729	Discontinued
0.7542	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4361	Phase 2
0.7533	Intermediate Similarity	NPD4625	Phase 3
0.7531	Intermediate Similarity	NPD6585	Discontinued
0.7515	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1465	Phase 2
0.7473	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD8312	Approved
0.7471	Intermediate Similarity	NPD8313	Approved
0.7457	Intermediate Similarity	NPD6104	Discontinued
0.7456	Intermediate Similarity	NPD3926	Phase 2
0.7455	Intermediate Similarity	NPD4288	Approved
0.7452	Intermediate Similarity	NPD2654	Approved
0.7451	Intermediate Similarity	NPD1933	Approved
0.7439	Intermediate Similarity	NPD7577	Discontinued
0.7431	Intermediate Similarity	NPD9545	Approved
0.7427	Intermediate Similarity	NPD3751	Discontinued
0.7415	Intermediate Similarity	NPD3972	Approved
0.7396	Intermediate Similarity	NPD5711	Approved
0.7396	Intermediate Similarity	NPD5710	Approved
0.7386	Intermediate Similarity	NPD4307	Phase 2
0.7386	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1613	Approved
0.7383	Intermediate Similarity	NPD3267	Approved
0.7383	Intermediate Similarity	NPD3266	Approved
0.7375	Intermediate Similarity	NPD7213	Phase 3
0.7375	Intermediate Similarity	NPD7212	Phase 2
0.7368	Intermediate Similarity	NPD6798	Discontinued
0.7368	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4287	Approved
0.7346	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7447	Phase 1
0.7326	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1241	Discontinued
0.7296	Intermediate Similarity	NPD7003	Approved
0.7294	Intermediate Similarity	NPD7229	Phase 3
0.7294	Intermediate Similarity	NPD3787	Discontinued
0.7292	Intermediate Similarity	NPD9493	Approved
0.7289	Intermediate Similarity	NPD5761	Phase 2
0.7289	Intermediate Similarity	NPD8455	Phase 2
0.7289	Intermediate Similarity	NPD5760	Phase 2
0.7287	Intermediate Similarity	NPD7585	Approved
0.7283	Intermediate Similarity	NPD6779	Approved
0.7283	Intermediate Similarity	NPD6780	Approved
0.7283	Intermediate Similarity	NPD6777	Approved
0.7283	Intermediate Similarity	NPD6778	Approved
0.7283	Intermediate Similarity	NPD6776	Approved
0.7283	Intermediate Similarity	NPD6781	Approved
0.7283	Intermediate Similarity	NPD6782	Approved
0.7278	Intermediate Similarity	NPD2424	Discontinued
0.7263	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5405	Approved
0.7261	Intermediate Similarity	NPD5406	Approved
0.7261	Intermediate Similarity	NPD5404	Approved
0.7261	Intermediate Similarity	NPD5408	Approved
0.7258	Intermediate Similarity	NPD7696	Phase 3
0.7258	Intermediate Similarity	NPD7698	Approved
0.7258	Intermediate Similarity	NPD7435	Discontinued
0.7258	Intermediate Similarity	NPD7697	Approved
0.7255	Intermediate Similarity	NPD3764	Approved
0.7255	Intermediate Similarity	NPD1296	Phase 2
0.725	Intermediate Similarity	NPD3887	Approved
0.725	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4749	Approved
0.7247	Intermediate Similarity	NPD8434	Phase 2
0.7247	Intermediate Similarity	NPD8150	Discontinued
0.7237	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7583	Approved
0.7233	Intermediate Similarity	NPD1652	Phase 2
0.7226	Intermediate Similarity	NPD230	Phase 1
0.7226	Intermediate Similarity	NPD6355	Discontinued
0.7222	Intermediate Similarity	NPD4661	Approved
0.7222	Intermediate Similarity	NPD4662	Approved
0.7219	Intermediate Similarity	NPD1019	Discontinued
0.7219	Intermediate Similarity	NPD7870	Phase 2
0.7219	Intermediate Similarity	NPD7871	Phase 2
0.7215	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3823	Discontinued
0.7191	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1608	Approved
0.7178	Intermediate Similarity	NPD6273	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