NPASS Compound

Structure

NPC300680 OpenBabel07101718252D 31 34 0 0 0 0 0 0 0 0999 V2000 3.9703 -1.4680 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7709 -0.3660 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7709 -0.3660 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 4.7709 1.3660 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 2.9921 -1.2601 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 4.2709 0.5000 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 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2709 0.5000 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 5.7709 1.3660 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 2.6831 -0.3090 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 3.2709 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 2.3230 -2.0032 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2709 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2709 2.2321 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 5 2 0 0 0 0 2 12 1 0 0 0 0 3 6 2 0 0 0 0 3 12 1 0 0 0 0 4 7 2 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 12 2 0 0 0 0 8 17 1 0 0 0 0 9 13 2 0 0 0 0 9 18 1 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 11 24 2 0 0 0 0 13 22 1 0 0 0 0 14 30 1 0 0 0 0 15 17 2 0 0 0 0 15 25 1 0 0 0 0 16 18 2 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 21 2 0 0 0 0 19 31 1 0 0 0 0 20 21 1 0 0 0 0 20 22 2 0 0 0 0 21 23 1 0 0 0 0 22 31 1 0 0 0 0 23 29 2 0 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.08
Volume:	410.823
LogP:	3.488
LogD:	2.455
LogS:	-4.047
# Rotatable Bonds:	4
TPSA:	141.34
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.284
Synthetic Accessibility Score:	2.965
Fsp3:	0.043
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.097
MDCK Permeability:	1.2660013453569263e-05
Pgp-inhibitor:	0.202
Pgp-substrate:	0.972
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.89
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	98.47211456298828%
Volume Distribution (VD):	0.397
Pgp-substrate:	4.113518238067627%

ADMET: Metabolism

CYP1A2-inhibitor:	0.909
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.169
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.555
CYP2C9-substrate:	0.795
CYP2D6-inhibitor:	0.131
CYP2D6-substrate:	0.765
CYP3A4-inhibitor:	0.273
CYP3A4-substrate:	0.12

ADMET: Excretion

Clearance (CL):	8.117
Half-life (T1/2):	0.898

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.67
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.163
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.725
Skin Sensitization:	0.794
Carcinogencity:	0.38
Eye Corrosion:	0.004
Eye Irritation:	0.914
Respiratory Toxicity:	0.076

Download Data

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

Natural Product: NPC300680

Natural Product ID:	NPC300680
*Common Name:**	Inoscavin C
IUPAC Name:	3-acetyl-2-(3,4-dihydroxyphenyl)-6-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]furo[3,2-c]pyran-4-one
Synonyms:	Inoscavin C
Standard InCHIKey:	HKRPUELQNBGEIC-GORDUTHDSA-N
Standard InCHI:	InChI=1S/C23H16O8/c1-11(24)20-21-19(31-22(20)13-4-7-16(26)18(28)9-13)10-14(30-23(21)29)5-2-12-3-6-15(25)17(27)8-12/h2-10,25-28H,1H3/b5-2+
SMILES:	Oc1ccc(cc1O)/C=C/c1oc(=O)c2c(c1)oc(c2C(=O)C)c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL205356
PubChem CID:	44410484
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001818] Furopyrans

*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
NPO33057	Inonotus xeranticus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16488146]
NPO33057	Inonotus xeranticus	Species	Hymenochaetaceae	Eukaryota	n.a.	chonan-si, Korea	2005-APR	PMID[16499338]
NPO41437	Inonotus obliquus + Phellinus punctatus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20830471]

☑ 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	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	>	100000.0	nM	PMID[524474]
NPT1	Others	Radical scavenging activity		IC50	=	7800.0	nM	PMID[524474]

☑ 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 NPC300680 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	1804
0.2-0.3	4227
0.3-0.4	10085
0.4-0.5	8063
0.5-0.6	4065
0.6-0.7	5978
0.7-0.8	5549
0.8-0.85	1958
0.85-0.9	533
0.9-0.95	45
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9805	High Similarity	NPC89131
0.9367	High Similarity	NPC29411
0.9317	High Similarity	NPC47386
0.9141	High Similarity	NPC261471
0.9136	High Similarity	NPC218533
0.9136	High Similarity	NPC78830
0.913	High Similarity	NPC86477
0.908	High Similarity	NPC247964
0.903	High Similarity	NPC164384
0.9024	High Similarity	NPC37606
0.8896	High Similarity	NPC50394
0.8889	High Similarity	NPC291110
0.8882	High Similarity	NPC312056
0.8882	High Similarity	NPC84515
0.8869	High Similarity	NPC97523
0.8862	High Similarity	NPC297807
0.8834	High Similarity	NPC277480
0.882	High Similarity	NPC188486
0.8812	High Similarity	NPC244750
0.8773	High Similarity	NPC37183
0.8765	High Similarity	NPC272722
0.8758	High Similarity	NPC115432
0.8758	High Similarity	NPC260296
0.8757	High Similarity	NPC47883
0.875	High Similarity	NPC98546
0.8742	High Similarity	NPC99199
0.8742	High Similarity	NPC80489
0.8734	High Similarity	NPC125300
0.8734	High Similarity	NPC41326
0.8727	High Similarity	NPC202470
0.8712	High Similarity	NPC133065
0.8696	High Similarity	NPC16935
0.8696	High Similarity	NPC196879
0.8688	High Similarity	NPC472461
0.8683	High Similarity	NPC473834
0.8683	High Similarity	NPC310794
0.8679	High Similarity	NPC472462
0.8679	High Similarity	NPC72370
0.8675	High Similarity	NPC131866
0.8671	High Similarity	NPC23668
0.8671	High Similarity	NPC193976
0.8671	High Similarity	NPC267091
0.8667	High Similarity	NPC186392
0.8667	High Similarity	NPC247973
0.8659	High Similarity	NPC45449
0.8659	High Similarity	NPC36320
0.8659	High Similarity	NPC39306
0.8659	High Similarity	NPC259007
0.8659	High Similarity	NPC329215
0.8659	High Similarity	NPC204088
0.8659	High Similarity	NPC38914
0.8647	High Similarity	NPC475996
0.8634	High Similarity	NPC268360
0.8623	High Similarity	NPC174700
0.8616	High Similarity	NPC207624
0.8616	High Similarity	NPC60972
0.8616	High Similarity	NPC39732
0.8616	High Similarity	NPC142308
0.8608	High Similarity	NPC230713
0.8608	High Similarity	NPC3825
0.8608	High Similarity	NPC78335
0.8608	High Similarity	NPC243891
0.8608	High Similarity	NPC167576
0.8608	High Similarity	NPC88804
0.8598	High Similarity	NPC155640
0.8598	High Similarity	NPC1755
0.8598	High Similarity	NPC39305
0.8598	High Similarity	NPC1706
0.8598	High Similarity	NPC263092
0.8598	High Similarity	NPC59295
0.858	High Similarity	NPC24258
0.8571	High Similarity	NPC45131
0.8571	High Similarity	NPC82217
0.8571	High Similarity	NPC13879
0.8571	High Similarity	NPC216842
0.8571	High Similarity	NPC476640
0.8563	High Similarity	NPC295436
0.8563	High Similarity	NPC120220
0.8562	High Similarity	NPC235333
0.8555	High Similarity	NPC248315
0.8554	High Similarity	NPC470704
0.8554	High Similarity	NPC241820
0.8553	High Similarity	NPC170169
0.8553	High Similarity	NPC58668
0.8553	High Similarity	NPC154345
0.8553	High Similarity	NPC106372
0.8553	High Similarity	NPC115324
0.8547	High Similarity	NPC154527
0.8545	High Similarity	NPC88243
0.8544	High Similarity	NPC178202
0.8537	High Similarity	NPC238995
0.8537	High Similarity	NPC144843
0.8535	High Similarity	NPC17816
0.8535	High Similarity	NPC472969
0.8535	High Similarity	NPC108406
0.8528	High Similarity	NPC328102
0.8528	High Similarity	NPC130955
0.8528	High Similarity	NPC476283
0.8526	High Similarity	NPC70136
0.8526	High Similarity	NPC155144
0.8521	High Similarity	NPC287243
0.8521	High Similarity	NPC227906
0.8519	High Similarity	NPC299520
0.8519	High Similarity	NPC129684
0.8512	High Similarity	NPC472584
0.8512	High Similarity	NPC54098
0.8512	High Similarity	NPC230619
0.8509	High Similarity	NPC4455
0.8509	High Similarity	NPC20830
0.8509	High Similarity	NPC128863
0.8509	High Similarity	NPC183597
0.8509	High Similarity	NPC50715
0.8509	High Similarity	NPC472280
0.8509	High Similarity	NPC268008
0.8509	High Similarity	NPC208197
0.8509	High Similarity	NPC201136
0.8509	High Similarity	NPC196439
0.8509	High Similarity	NPC146165
0.8509	High Similarity	NPC92659
0.8509	High Similarity	NPC227325
0.8509	High Similarity	NPC163780
0.8509	High Similarity	NPC2476
0.8509	High Similarity	NPC256612
0.8509	High Similarity	NPC297531
0.8509	High Similarity	NPC167815
0.8509	High Similarity	NPC148938
0.8509	High Similarity	NPC280339
0.8509	High Similarity	NPC213936
0.8509	High Similarity	NPC138360
0.8503	High Similarity	NPC280493
0.85	High Similarity	NPC63187
0.85	High Similarity	NPC157784
0.85	High Similarity	NPC67654
0.85	High Similarity	NPC37684
0.8497	Intermediate Similarity	NPC226725
0.8494	Intermediate Similarity	NPC323137
0.8494	Intermediate Similarity	NPC13481
0.8494	Intermediate Similarity	NPC207575
0.8491	Intermediate Similarity	NPC184136
0.8491	Intermediate Similarity	NPC295036
0.8485	Intermediate Similarity	NPC272750
0.8485	Intermediate Similarity	NPC173729
0.8485	Intermediate Similarity	NPC477689
0.8485	Intermediate Similarity	NPC134047
0.8485	Intermediate Similarity	NPC223006
0.8481	Intermediate Similarity	NPC107636
0.8481	Intermediate Similarity	NPC12367
0.8481	Intermediate Similarity	NPC118726
0.8481	Intermediate Similarity	NPC98809
0.8481	Intermediate Similarity	NPC476394
0.8476	Intermediate Similarity	NPC112418
0.8476	Intermediate Similarity	NPC469889
0.8471	Intermediate Similarity	NPC8127
0.8471	Intermediate Similarity	NPC49667
0.8466	Intermediate Similarity	NPC172770
0.8466	Intermediate Similarity	NPC185258
0.8462	Intermediate Similarity	NPC279121
0.8462	Intermediate Similarity	NPC117450
0.8462	Intermediate Similarity	NPC233956
0.8457	Intermediate Similarity	NPC265511
0.8457	Intermediate Similarity	NPC137100
0.8457	Intermediate Similarity	NPC472455
0.8457	Intermediate Similarity	NPC54928
0.8457	Intermediate Similarity	NPC247677
0.8457	Intermediate Similarity	NPC160015
0.8457	Intermediate Similarity	NPC3980
0.8452	Intermediate Similarity	NPC476641
0.8448	Intermediate Similarity	NPC139683
0.8448	Intermediate Similarity	NPC73929
0.8448	Intermediate Similarity	NPC47905
0.8447	Intermediate Similarity	NPC475895
0.8447	Intermediate Similarity	NPC47781
0.8447	Intermediate Similarity	NPC70433
0.8447	Intermediate Similarity	NPC227337
0.8447	Intermediate Similarity	NPC273462
0.8447	Intermediate Similarity	NPC1477
0.8447	Intermediate Similarity	NPC250822
0.8447	Intermediate Similarity	NPC25127
0.8447	Intermediate Similarity	NPC49402
0.8447	Intermediate Similarity	NPC75279
0.8447	Intermediate Similarity	NPC255350
0.8447	Intermediate Similarity	NPC183878
0.8447	Intermediate Similarity	NPC160951
0.8447	Intermediate Similarity	NPC22519
0.8447	Intermediate Similarity	NPC176775
0.8447	Intermediate Similarity	NPC89474
0.8447	Intermediate Similarity	NPC145379
0.8447	Intermediate Similarity	NPC69394
0.8447	Intermediate Similarity	NPC274327
0.8447	Intermediate Similarity	NPC213608
0.8447	Intermediate Similarity	NPC231018
0.8447	Intermediate Similarity	NPC170492
0.8447	Intermediate Similarity	NPC189130
0.8447	Intermediate Similarity	NPC33051
0.8447	Intermediate Similarity	NPC287504
0.8447	Intermediate Similarity	NPC276409
0.8442	Intermediate Similarity	NPC326065
0.8439	Intermediate Similarity	NPC71260
0.8438	Intermediate Similarity	NPC260895
0.8438	Intermediate Similarity	NPC304295

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 NPC300680 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	951
0.2-0.3	1678
0.3-0.4	2657
0.4-0.5	1933
0.5-0.6	1088
0.6-0.7	338
0.7-0.8	110
0.8-0.85	35
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD1511	Approved
0.8447	Intermediate Similarity	NPD2801	Approved
0.8443	Intermediate Similarity	NPD3818	Discontinued
0.8431	Intermediate Similarity	NPD2344	Approved
0.8354	Intermediate Similarity	NPD1512	Approved
0.8344	Intermediate Similarity	NPD3882	Suspended
0.8344	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6232	Discontinued
0.8293	Intermediate Similarity	NPD3749	Approved
0.8282	Intermediate Similarity	NPD3817	Phase 2
0.8274	Intermediate Similarity	NPD7473	Discontinued
0.8272	Intermediate Similarity	NPD1934	Approved
0.8263	Intermediate Similarity	NPD3926	Phase 2
0.8217	Intermediate Similarity	NPD2309	Approved
0.811	Intermediate Similarity	NPD1465	Phase 2
0.8107	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD6166	Phase 2
0.8035	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD7819	Suspended
0.7989	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3226	Approved
0.7965	Intermediate Similarity	NPD7054	Approved
0.7964	Intermediate Similarity	NPD7075	Discontinued
0.7963	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7472	Approved
0.7919	Intermediate Similarity	NPD7074	Phase 3
0.7917	Intermediate Similarity	NPD919	Approved
0.7888	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7411	Suspended
0.7874	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD6797	Phase 2
0.787	Intermediate Similarity	NPD5494	Approved
0.7862	Intermediate Similarity	NPD1243	Approved
0.7857	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD920	Approved
0.7831	Intermediate Similarity	NPD6801	Discontinued
0.7829	Intermediate Similarity	NPD7251	Discontinued
0.7818	Intermediate Similarity	NPD4380	Phase 2
0.7812	Intermediate Similarity	NPD4628	Phase 3
0.7812	Intermediate Similarity	NPD3750	Approved
0.7791	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2935	Discontinued
0.7784	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6799	Approved
0.7759	Intermediate Similarity	NPD5844	Phase 1
0.7756	Intermediate Similarity	NPD230	Phase 1
0.7756	Intermediate Similarity	NPD447	Suspended
0.775	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD5402	Approved
0.773	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD2799	Discontinued
0.7722	Intermediate Similarity	NPD1510	Phase 2
0.7722	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD1247	Approved
0.7711	Intermediate Similarity	NPD6599	Discontinued
0.7709	Intermediate Similarity	NPD8434	Phase 2
0.7692	Intermediate Similarity	NPD7768	Phase 2
0.7692	Intermediate Similarity	NPD943	Approved
0.7688	Intermediate Similarity	NPD1549	Phase 2
0.7688	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7808	Phase 3
0.7677	Intermediate Similarity	NPD3764	Approved
0.7677	Intermediate Similarity	NPD2313	Discontinued
0.7673	Intermediate Similarity	NPD2796	Approved
0.764	Intermediate Similarity	NPD2800	Approved
0.7633	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD2296	Approved
0.7627	Intermediate Similarity	NPD7685	Pre-registration
0.7625	Intermediate Similarity	NPD2346	Discontinued
0.7625	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2534	Approved
0.7622	Intermediate Similarity	NPD2532	Approved
0.7622	Intermediate Similarity	NPD2533	Approved
0.7616	Intermediate Similarity	NPD6959	Discontinued
0.7607	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1240	Approved
0.7556	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6190	Approved
0.753	Intermediate Similarity	NPD5403	Approved
0.7516	Intermediate Similarity	NPD1471	Phase 3
0.7514	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1607	Approved
0.7471	Intermediate Similarity	NPD6808	Phase 2
0.7468	Intermediate Similarity	NPD1203	Approved
0.7458	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD3268	Approved
0.7429	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD5401	Approved
0.741	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD5953	Discontinued
0.7355	Intermediate Similarity	NPD2797	Approved
0.7351	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD8313	Approved
0.7348	Intermediate Similarity	NPD8312	Approved
0.7346	Intermediate Similarity	NPD1551	Phase 2
0.7338	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4287	Approved
0.7325	Intermediate Similarity	NPD6832	Phase 2
0.7312	Intermediate Similarity	NPD1933	Approved
0.731	Intermediate Similarity	NPD6280	Approved
0.731	Intermediate Similarity	NPD6279	Approved
0.731	Intermediate Similarity	NPD37	Approved
0.7308	Intermediate Similarity	NPD2798	Approved
0.7303	Intermediate Similarity	NPD17	Approved
0.7284	Intermediate Similarity	NPD4308	Phase 3
0.7284	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7033	Discontinued
0.7283	Intermediate Similarity	NPD4965	Approved
0.7283	Intermediate Similarity	NPD4967	Phase 2
0.7283	Intermediate Similarity	NPD4966	Approved
0.7273	Intermediate Similarity	NPD9717	Approved
0.7273	Intermediate Similarity	NPD9269	Phase 2
0.7261	Intermediate Similarity	NPD9494	Approved
0.7239	Intermediate Similarity	NPD5404	Approved
0.7239	Intermediate Similarity	NPD5405	Approved
0.7239	Intermediate Similarity	NPD5406	Approved
0.7239	Intermediate Similarity	NPD5408	Approved
0.7233	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7228	Approved
0.7207	Intermediate Similarity	NPD3751	Discontinued
0.7205	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7229	Phase 3
0.7169	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7286	Phase 2
0.7152	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6385	Approved
0.7151	Intermediate Similarity	NPD6386	Approved
0.7143	Intermediate Similarity	NPD7390	Discontinued
0.7135	Intermediate Similarity	NPD5242	Approved
0.7135	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3266	Approved
0.7134	Intermediate Similarity	NPD3267	Approved
0.7126	Intermediate Similarity	NPD2354	Approved
0.7125	Intermediate Similarity	NPD411	Approved
0.7104	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7266	Discontinued
0.7081	Intermediate Similarity	NPD6233	Phase 2
0.7079	Intermediate Similarity	NPD5711	Approved
0.7079	Intermediate Similarity	NPD5710	Approved
0.7076	Intermediate Similarity	NPD1653	Approved
0.707	Intermediate Similarity	NPD3225	Approved
0.7069	Intermediate Similarity	NPD5760	Phase 2
0.7069	Intermediate Similarity	NPD5761	Phase 2
0.7066	Intermediate Similarity	NPD8166	Discontinued
0.7063	Intermediate Similarity	NPD3027	Phase 3
0.7063	Intermediate Similarity	NPD7095	Approved
0.7059	Intermediate Similarity	NPD6273	Approved
0.7059	Intermediate Similarity	NPD9545	Approved
0.7056	Intermediate Similarity	NPD8151	Discontinued
0.7051	Intermediate Similarity	NPD3972	Approved
0.7043	Intermediate Similarity	NPD8150	Discontinued
0.7037	Intermediate Similarity	NPD1613	Approved
0.7037	Intermediate Similarity	NPD4307	Phase 2
0.7037	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6100	Approved
0.703	Intermediate Similarity	NPD6099	Approved
0.7025	Intermediate Similarity	NPD1470	Approved
0.7022	Intermediate Similarity	NPD8127	Discontinued
0.7019	Intermediate Similarity	NPD6798	Discontinued
0.7016	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD9268	Approved
0.6995	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6355	Discontinued
0.6983	Remote Similarity	NPD3787	Discontinued
0.6974	Remote Similarity	NPD7435	Discontinued
0.6971	Remote Similarity	NPD8455	Phase 2
0.6964	Remote Similarity	NPD7003	Approved
0.6964	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4110	Phase 3
0.6962	Remote Similarity	NPD1876	Approved
0.6957	Remote Similarity	NPD7039	Approved
0.6957	Remote Similarity	NPD7038	Approved
0.6951	Remote Similarity	NPD6651	Approved
0.6949	Remote Similarity	NPD6971	Discontinued
0.6943	Remote Similarity	NPD1481	Phase 2
0.6936	Remote Similarity	NPD7458	Discontinued
0.6932	Remote Similarity	NPD4288	Approved
0.6923	Remote Similarity	NPD7177	Discontinued
0.6918	Remote Similarity	NPD1164	Approved
0.6907	Remote Similarity	NPD6781	Approved
0.6907	Remote Similarity	NPD6778	Approved
0.6907	Remote Similarity	NPD6782	Approved
0.6907	Remote Similarity	NPD6780	Approved
0.6907	Remote Similarity	NPD6777	Approved
0.6907	Remote Similarity	NPD6776	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