NPASS Compound

Structure

CID168085 OpenBabel06191715542D 25 28 0 0 1 0 0 0 0 0999 V2000 -5.6369 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6369 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 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 -5.1369 -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 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 2 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 -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 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 -3.5491 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 10 1 0 0 0 0 3 5 1 0 0 0 0 3 11 2 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 24 1 0 0 0 0 11 14 1 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 19 2 0 0 0 0 14 20 1 0 0 0 0 15 10 1 1 0 0 0 15 25 1 0 0 0 0 16 25 1 0 0 0 0 17 18 2 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 22 1 0 0 0 0 20 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.1
Volume:	340.473
LogP:	4.179
LogD:	2.93
LogS:	-3.685
# Rotatable Bonds:	2
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.697
Synthetic Accessibility Score:	3.262
Fsp3:	0.15
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:	-4.816
MDCK Permeability:	8.356964826816693e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	98.16422271728516%
Volume Distribution (VD):	0.439
Pgp-substrate:	1.324060082435608%

ADMET: Metabolism

CYP1A2-inhibitor:	0.828
CYP1A2-substrate:	0.381
CYP2C19-inhibitor:	0.856
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.819
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.536
CYP2D6-substrate:	0.84
CYP3A4-inhibitor:	0.328
CYP3A4-substrate:	0.146

ADMET: Excretion

Clearance (CL):	4.118
Half-life (T1/2):	0.533

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.68
Drug-inuced Liver Injury (DILI):	0.724
AMES Toxicity:	0.232
Rat Oral Acute Toxicity:	0.824
Maximum Recommended Daily Dose:	0.874
Skin Sensitization:	0.876
Carcinogencity:	0.582
Eye Corrosion:	0.003
Eye Irritation:	0.749
Respiratory Toxicity:	0.703

Download Data

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

Natural Product: NPC168085

Natural Product ID:	NPC168085
*Common Name:**	Licoagroisoflavone
IUPAC Name:	(2R)-4-hydroxy-6-(4-hydroxyphenyl)-2-prop-1-en-2-yl-2,3-dihydrofuro[3,2-g]chromen-5-one
Synonyms:	Licoagroisoflavone
Standard InCHIKey:	CQXOSSCKEFRIBR-OAHLLOKOSA-N
Standard InCHI:	InChI=1S/C20H16O5/c1-10(2)15-7-13-16(25-15)8-17-18(19(13)22)20(23)14(9-24-17)11-3-5-12(21)6-4-11/h3-6,8-9,15,21-22H,1,7H2,2H3/t15-/m1/s1
SMILES:	C=C(C)[C@H]1Cc2c(cc3c(c2O)c(=O)c(co3)c2ccc(cc2)O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689288
PubChem CID:	636883
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003526] 6-prenylated 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
NPO21353	Crotalaria lachnophora	Species	Fabaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21265557]
NPO21353	Crotalaria lachnophora	Species	Fabaceae	Eukaryota	whole plant	Dschang (west region of Cameroon)	2007-SEP	PMID[21265557]
NPO15413	Glycyrrhiza pallidiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16193	Glycyrrhiza sp.	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15413	Glycyrrhiza pallidiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15413	Glycyrrhiza pallidiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21353	Crotalaria lachnophora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15413	Glycyrrhiza pallidiflora	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	9.3	mm	PMID[490790]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	7.3	mm	PMID[490790]

☑ 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 NPC168085 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	388
0.1-0.2	1648
0.2-0.3	3733
0.3-0.4	9810
0.4-0.5	8760
0.5-0.6	3800
0.6-0.7	5633
0.7-0.8	4723
0.8-0.85	2118
0.85-0.9	1535
0.9-0.95	457
0.95-1	92

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC317492
0.9724	High Similarity	NPC327269
0.9724	High Similarity	NPC31627
0.9724	High Similarity	NPC476238
0.9722	High Similarity	NPC476185
0.9722	High Similarity	NPC321896
0.9655	High Similarity	NPC471675
0.9648	High Similarity	NPC224714
0.9589	High Similarity	NPC473996
0.9589	High Similarity	NPC285623
0.9586	High Similarity	NPC61258
0.9586	High Similarity	NPC472421
0.958	High Similarity	NPC472629
0.9577	High Similarity	NPC68104
0.9577	High Similarity	NPC51887
0.9577	High Similarity	NPC221432
0.9577	High Similarity	NPC257097
0.9577	High Similarity	NPC150408
0.9577	High Similarity	NPC39329
0.9577	High Similarity	NPC475705
0.9577	High Similarity	NPC476178
0.9577	High Similarity	NPC143896
0.9577	High Similarity	NPC91560
0.9577	High Similarity	NPC164980
0.9577	High Similarity	NPC117836
0.9577	High Similarity	NPC75049
0.9577	High Similarity	NPC149026
0.9577	High Similarity	NPC175504
0.9577	High Similarity	NPC310130
0.9577	High Similarity	NPC169591
0.9574	High Similarity	NPC110969
0.9574	High Similarity	NPC469404
0.9521	High Similarity	NPC474744
0.9521	High Similarity	NPC472580
0.9521	High Similarity	NPC472636
0.9521	High Similarity	NPC474772
0.9521	High Similarity	NPC472423
0.9521	High Similarity	NPC290671
0.9517	High Similarity	NPC5173
0.9514	High Similarity	NPC97716
0.9514	High Similarity	NPC79469
0.9514	High Similarity	NPC237635
0.9514	High Similarity	NPC104406
0.9514	High Similarity	NPC201731
0.9514	High Similarity	NPC23728
0.9514	High Similarity	NPC110303
0.9514	High Similarity	NPC296998
0.9514	High Similarity	NPC473077
0.9514	High Similarity	NPC24673
0.951	High Similarity	NPC273538
0.951	High Similarity	NPC87486
0.951	High Similarity	NPC209040
0.951	High Similarity	NPC470890
0.951	High Similarity	NPC473013
0.951	High Similarity	NPC319752
0.951	High Similarity	NPC236766
0.951	High Similarity	NPC311741
0.951	High Similarity	NPC234629
0.951	High Similarity	NPC124780
0.951	High Similarity	NPC216538
0.951	High Similarity	NPC473015
0.951	High Similarity	NPC197252
0.9507	High Similarity	NPC324134
0.9507	High Similarity	NPC10937
0.9507	High Similarity	NPC40833
0.9507	High Similarity	NPC125855
0.9507	High Similarity	NPC182852
0.9507	High Similarity	NPC161506
0.9507	High Similarity	NPC296917
0.9507	High Similarity	NPC37496
0.9507	High Similarity	NPC226636
0.9507	High Similarity	NPC166934
0.9507	High Similarity	NPC194432
0.9507	High Similarity	NPC306829
0.9507	High Similarity	NPC32739
0.9507	High Similarity	NPC76338
0.9507	High Similarity	NPC223500
0.9507	High Similarity	NPC107572
0.9507	High Similarity	NPC78
0.9507	High Similarity	NPC11561
0.9507	High Similarity	NPC265040
0.9507	High Similarity	NPC228504
0.9507	High Similarity	NPC177354
0.9507	High Similarity	NPC64915
0.9507	High Similarity	NPC324436
0.9507	High Similarity	NPC1089
0.9507	High Similarity	NPC167624
0.9507	High Similarity	NPC220998
0.9507	High Similarity	NPC328164
0.9507	High Similarity	NPC66515
0.9507	High Similarity	NPC76372
0.9507	High Similarity	NPC227579
0.9507	High Similarity	NPC148757
0.9507	High Similarity	NPC166482
0.9504	High Similarity	NPC48624
0.9504	High Similarity	NPC219917
0.9504	High Similarity	NPC213659
0.9504	High Similarity	NPC144118
0.9504	High Similarity	NPC172986
0.9504	High Similarity	NPC80962
0.9504	High Similarity	NPC261227
0.9504	High Similarity	NPC241100
0.9504	High Similarity	NPC326109
0.9504	High Similarity	NPC270883
0.9504	High Similarity	NPC215311
0.9504	High Similarity	NPC159275
0.9504	High Similarity	NPC204985
0.9504	High Similarity	NPC172250
0.9504	High Similarity	NPC259166
0.9456	High Similarity	NPC477957
0.9452	High Similarity	NPC472633
0.9452	High Similarity	NPC37348
0.9448	High Similarity	NPC160821
0.9448	High Similarity	NPC266572
0.9448	High Similarity	NPC6511
0.9448	High Similarity	NPC39195
0.9448	High Similarity	NPC132592
0.9444	High Similarity	NPC474161
0.9444	High Similarity	NPC187282
0.9444	High Similarity	NPC142405
0.9444	High Similarity	NPC20488
0.9444	High Similarity	NPC83357
0.9444	High Similarity	NPC178343
0.9444	High Similarity	NPC24136
0.9444	High Similarity	NPC5820
0.9444	High Similarity	NPC267375
0.9444	High Similarity	NPC124729
0.9444	High Similarity	NPC290133
0.9444	High Similarity	NPC176229
0.9444	High Similarity	NPC475052
0.9444	High Similarity	NPC214774
0.9444	High Similarity	NPC67805
0.9444	High Similarity	NPC476088
0.9444	High Similarity	NPC470647
0.9444	High Similarity	NPC88964
0.9444	High Similarity	NPC111786
0.9444	High Similarity	NPC312973
0.9444	High Similarity	NPC301276
0.9444	High Similarity	NPC54577
0.9444	High Similarity	NPC195621
0.9444	High Similarity	NPC306488
0.9444	High Similarity	NPC246948
0.9441	High Similarity	NPC24821
0.9441	High Similarity	NPC214166
0.9441	High Similarity	NPC316816
0.9441	High Similarity	NPC293053
0.9441	High Similarity	NPC77794
0.9441	High Similarity	NPC223812
0.9441	High Similarity	NPC478086
0.9441	High Similarity	NPC81697
0.9441	High Similarity	NPC212932
0.9441	High Similarity	NPC125894
0.9441	High Similarity	NPC185276
0.9441	High Similarity	NPC107177
0.9441	High Similarity	NPC18585
0.9441	High Similarity	NPC85162
0.9441	High Similarity	NPC166138
0.9441	High Similarity	NPC9117
0.9441	High Similarity	NPC278249
0.9441	High Similarity	NPC190637
0.9441	High Similarity	NPC106985
0.9437	High Similarity	NPC321980
0.9437	High Similarity	NPC52789
0.9437	High Similarity	NPC470087
0.9437	High Similarity	NPC96408
0.9437	High Similarity	NPC279650
0.9437	High Similarity	NPC248372
0.9437	High Similarity	NPC166689
0.9437	High Similarity	NPC26051
0.9437	High Similarity	NPC324386
0.9437	High Similarity	NPC17170
0.9437	High Similarity	NPC156590
0.9437	High Similarity	NPC213322
0.9437	High Similarity	NPC103362
0.9437	High Similarity	NPC312391
0.9437	High Similarity	NPC110038
0.9437	High Similarity	NPC205006
0.9437	High Similarity	NPC118840
0.9437	High Similarity	NPC147688
0.9437	High Similarity	NPC55832
0.9437	High Similarity	NPC3188
0.9437	High Similarity	NPC258630
0.9437	High Similarity	NPC268204
0.9437	High Similarity	NPC64908
0.9437	High Similarity	NPC156190
0.9437	High Similarity	NPC282300
0.9437	High Similarity	NPC4743
0.9437	High Similarity	NPC470089
0.9433	High Similarity	NPC18260
0.9433	High Similarity	NPC283429
0.9433	High Similarity	NPC96565
0.9433	High Similarity	NPC295384
0.9433	High Similarity	NPC220062
0.9433	High Similarity	NPC78913
0.9433	High Similarity	NPC53181
0.9433	High Similarity	NPC55018
0.9433	High Similarity	NPC216978
0.9433	High Similarity	NPC217186
0.9433	High Similarity	NPC301217
0.9433	High Similarity	NPC137009

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 NPC168085 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	951
0.2-0.3	1520
0.3-0.4	2598
0.4-0.5	1998
0.5-0.6	1173
0.6-0.7	381
0.7-0.8	120
0.8-0.85	41
0.85-0.9	24
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.951	High Similarity	NPD4378	Clinical (unspecified phase)
0.9225	High Similarity	NPD1549	Phase 2
0.922	High Similarity	NPD2796	Approved
0.9189	High Similarity	NPD4380	Phase 2
0.9155	High Similarity	NPD1550	Clinical (unspecified phase)
0.9155	High Similarity	NPD1552	Clinical (unspecified phase)
0.9149	High Similarity	NPD1510	Phase 2
0.9133	High Similarity	NPD2393	Clinical (unspecified phase)
0.911	High Similarity	NPD7410	Clinical (unspecified phase)
0.8954	High Similarity	NPD7075	Discontinued
0.8947	High Similarity	NPD8443	Clinical (unspecified phase)
0.8882	High Similarity	NPD7096	Clinical (unspecified phase)
0.8874	High Similarity	NPD7411	Suspended
0.8865	High Similarity	NPD1240	Approved
0.8831	High Similarity	NPD4381	Clinical (unspecified phase)
0.8816	High Similarity	NPD6801	Discontinued
0.8816	High Similarity	NPD1934	Approved
0.8758	High Similarity	NPD7819	Suspended
0.8741	High Similarity	NPD1607	Approved
0.8658	High Similarity	NPD1511	Approved
0.8645	High Similarity	NPD3882	Suspended
0.8639	High Similarity	NPD2800	Approved
0.8636	High Similarity	NPD2801	Approved
0.8625	High Similarity	NPD3818	Discontinued
0.8609	High Similarity	NPD920	Approved
0.8599	High Similarity	NPD5494	Approved
0.8571	High Similarity	NPD7804	Clinical (unspecified phase)
0.8544	High Similarity	NPD6959	Discontinued
0.8543	High Similarity	NPD1512	Approved
0.8533	High Similarity	NPD6799	Approved
0.8526	High Similarity	NPD7768	Phase 2
0.8514	High Similarity	NPD1243	Approved
0.8514	High Similarity	NPD7421	Clinical (unspecified phase)
0.85	High Similarity	NPD7852	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD3750	Approved
0.8415	Intermediate Similarity	NPD6559	Discontinued
0.8385	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD6166	Phase 2
0.8385	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD2534	Approved
0.8355	Intermediate Similarity	NPD2533	Approved
0.8355	Intermediate Similarity	NPD2532	Approved
0.8354	Intermediate Similarity	NPD3749	Approved
0.8344	Intermediate Similarity	NPD3817	Phase 2
0.8323	Intermediate Similarity	NPD6599	Discontinued
0.8311	Intermediate Similarity	NPD2935	Discontinued
0.8311	Intermediate Similarity	NPD1551	Phase 2
0.8255	Intermediate Similarity	NPD2344	Approved
0.8247	Intermediate Similarity	NPD5403	Approved
0.8232	Intermediate Similarity	NPD7054	Approved
0.8207	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD2313	Discontinued
0.82	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7074	Phase 3
0.8182	Intermediate Similarity	NPD7472	Approved
0.8176	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6797	Phase 2
0.8133	Intermediate Similarity	NPD5953	Discontinued
0.8121	Intermediate Similarity	NPD3748	Approved
0.8121	Intermediate Similarity	NPD7286	Phase 2
0.8121	Intermediate Similarity	NPD2799	Discontinued
0.8117	Intermediate Similarity	NPD5401	Approved
0.8113	Intermediate Similarity	NPD5402	Approved
0.8108	Intermediate Similarity	NPD6651	Approved
0.8092	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD1247	Approved
0.8084	Intermediate Similarity	NPD7251	Discontinued
0.8075	Intermediate Similarity	NPD919	Approved
0.8039	Intermediate Similarity	NPD2309	Approved
0.8037	Intermediate Similarity	NPD6232	Discontinued
0.8036	Intermediate Similarity	NPD7808	Phase 3
0.8012	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD7033	Discontinued
0.7974	Intermediate Similarity	NPD4628	Phase 3
0.7959	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD3226	Approved
0.7886	Intermediate Similarity	NPD4363	Phase 3
0.7886	Intermediate Similarity	NPD4360	Phase 2
0.7881	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1203	Approved
0.7841	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD4361	Phase 2
0.7823	Intermediate Similarity	NPD4908	Phase 1
0.7823	Intermediate Similarity	NPD6832	Phase 2
0.7808	Intermediate Similarity	NPD2798	Approved
0.7801	Intermediate Similarity	NPD1548	Phase 1
0.7778	Intermediate Similarity	NPD2346	Discontinued
0.7771	Intermediate Similarity	NPD3926	Phase 2
0.7751	Intermediate Similarity	NPD1729	Discontinued
0.7733	Intermediate Similarity	NPD943	Approved
0.7718	Intermediate Similarity	NPD3268	Approved
0.7712	Intermediate Similarity	NPD6099	Approved
0.7712	Intermediate Similarity	NPD6100	Approved
0.7711	Intermediate Similarity	NPD5711	Approved
0.7711	Intermediate Similarity	NPD5710	Approved
0.7708	Intermediate Similarity	NPD1610	Phase 2
0.7707	Intermediate Similarity	NPD7390	Discontinued
0.7706	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD5124	Phase 1
0.7682	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2654	Approved
0.7673	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD9717	Approved
0.7647	Intermediate Similarity	NPD4308	Phase 3
0.7628	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2797	Approved
0.7605	Intermediate Similarity	NPD7229	Phase 3
0.7586	Intermediate Similarity	NPD422	Phase 1
0.7566	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7584	Approved
0.75	Intermediate Similarity	NPD5760	Phase 2
0.75	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD5761	Phase 2
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1613	Approved
0.7483	Intermediate Similarity	NPD3764	Approved
0.7472	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7458	Discontinued
0.7469	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD2296	Approved
0.7455	Intermediate Similarity	NPD4288	Approved
0.7451	Intermediate Similarity	NPD230	Phase 1
0.7443	Intermediate Similarity	NPD8434	Phase 2
0.7439	Intermediate Similarity	NPD6844	Discontinued
0.7436	Intermediate Similarity	NPD6002	Phase 3
0.7436	Intermediate Similarity	NPD6004	Phase 3
0.7436	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6005	Phase 3
0.7436	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1471	Phase 3
0.7432	Intermediate Similarity	NPD3225	Approved
0.7431	Intermediate Similarity	NPD9545	Approved
0.7417	Intermediate Similarity	NPD4625	Phase 3
0.7415	Intermediate Similarity	NPD3972	Approved
0.74	Intermediate Similarity	NPD2861	Phase 2
0.7389	Intermediate Similarity	NPD2424	Discontinued
0.7386	Intermediate Similarity	NPD4307	Phase 2
0.7383	Intermediate Similarity	NPD3267	Approved
0.7383	Intermediate Similarity	NPD3266	Approved
0.7378	Intermediate Similarity	NPD5889	Approved
0.7378	Intermediate Similarity	NPD5890	Approved
0.7377	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD8313	Approved
0.7371	Intermediate Similarity	NPD8312	Approved
0.7368	Intermediate Similarity	NPD6798	Discontinued
0.736	Intermediate Similarity	NPD4287	Approved
0.7351	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6355	Discontinued
0.7338	Intermediate Similarity	NPD1933	Approved
0.7338	Intermediate Similarity	NPD447	Suspended
0.7337	Intermediate Similarity	NPD7199	Phase 2
0.7333	Intermediate Similarity	NPD37	Approved
0.7333	Intermediate Similarity	NPD6280	Approved
0.7333	Intermediate Similarity	NPD1019	Discontinued
0.7333	Intermediate Similarity	NPD6279	Approved
0.7326	Intermediate Similarity	NPD3751	Discontinued
0.7324	Intermediate Similarity	NPD1241	Discontinued
0.7321	Intermediate Similarity	NPD6234	Discontinued
0.731	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2403	Approved
0.7305	Intermediate Similarity	NPD4965	Approved
0.7305	Intermediate Similarity	NPD4966	Approved
0.7305	Intermediate Similarity	NPD4967	Phase 2
0.7303	Intermediate Similarity	NPD3027	Phase 3
0.7297	Intermediate Similarity	NPD1608	Approved
0.7296	Intermediate Similarity	NPD7003	Approved
0.7294	Intermediate Similarity	NPD6808	Phase 2
0.7292	Intermediate Similarity	NPD9493	Approved
0.7285	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6273	Approved
0.7267	Intermediate Similarity	NPD1164	Approved
0.7267	Intermediate Similarity	NPD1470	Approved
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
0.7257	Intermediate Similarity	NPD6104	Discontinued
0.7255	Intermediate Similarity	NPD411	Approved
0.7255	Intermediate Similarity	NPD1296	Phase 2
0.7251	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1652	Phase 2
0.723	Intermediate Similarity	NPD1201	Approved
0.7222	Intermediate Similarity	NPD4661	Approved
0.7222	Intermediate Similarity	NPD4662	Approved
0.7212	Intermediate Similarity	NPD6585	Discontinued
0.7208	Intermediate Similarity	NPD6233	Phase 2
0.72	Intermediate Similarity	NPD3823	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