NPASS Compound

Structure

CID292794 OpenBabel06191716102D 22 25 0 0 0 0 0 0 0 0999 V2000 5.6752 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3662 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3662 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 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 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 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 5 1 0 0 0 0 2 19 1 0 0 0 0 3 6 2 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 4 22 1 0 0 0 0 5 7 2 0 0 0 0 5 20 1 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 9 2 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 16 2 0 0 0 0 11 17 2 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.04
Volume:	276.847
LogP:	3.169
LogD:	2.468
LogS:	-4.567
# Rotatable Bonds:	1
TPSA:	95.2
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.732
Synthetic Accessibility Score:	3.105
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.78
MDCK Permeability:	1.828875429055188e-05
Pgp-inhibitor:	0.955
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	97.29435729980469%
Volume Distribution (VD):	0.405
Pgp-substrate:	3.9483704566955566%

ADMET: Metabolism

CYP1A2-inhibitor:	0.878
CYP1A2-substrate:	0.855
CYP2C19-inhibitor:	0.194
CYP2C19-substrate:	0.111
CYP2C9-inhibitor:	0.637
CYP2C9-substrate:	0.761
CYP2D6-inhibitor:	0.412
CYP2D6-substrate:	0.248
CYP3A4-inhibitor:	0.702
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	13.496
Half-life (T1/2):	0.092

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.214
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.895
Rat Oral Acute Toxicity:	0.858
Maximum Recommended Daily Dose:	0.253
Skin Sensitization:	0.16
Carcinogencity:	0.931
Eye Corrosion:	0.006
Eye Irritation:	0.867
Respiratory Toxicity:	0.373

Download Data

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

Natural Product: NPC292794

Natural Product ID:	NPC292794
*Common Name:**	Ventilone B
IUPAC Name:	10-hydroxy-4-methoxy-8-methyl-[2]benzofuro[6,5-f][1,3]benzodioxole-5,9-dione
Synonyms:
Standard InCHIKey:	SWAYFTFGBCOVIO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O7/c1-5-7-6(3-20-5)10(16)9-8(11(7)17)12(18)14-15(13(9)19-2)22-4-21-14/h3,18H,4H2,1-2H3
SMILES:	Cc1c2c(co1)C(=O)c1c(C2=O)c(c2c(c1OC)OCO2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2269917
PubChem CID:	76326825
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans [CHEMONTID:0004792] Furanonaphthodioxoles

*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
NPO8179	Laccaria amethystea	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11213295]
NPO8179	Laccaria amethystea	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2091	Abies pectinata	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO835	Diatraea saccharalis	Species	Crambidae	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	8

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1369	Organism	Henosepilachna vigintioctopunctata	Henosepilachna vigintioctopunctata	Activity	=	0.19	cm2	PMID[478285]
NPT1369	Organism	Henosepilachna vigintioctopunctata	Henosepilachna vigintioctopunctata	Activity	=	0.37	cm2	PMID[478285]
NPT1369	Organism	Henosepilachna vigintioctopunctata	Henosepilachna vigintioctopunctata	Activity	=	0.56	cm2	PMID[478285]
NPT1369	Organism	Henosepilachna vigintioctopunctata	Henosepilachna vigintioctopunctata	Activity	=	31.0	%	PMID[478285]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	13.0	cm2	PMID[478285]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	23.0	cm2	PMID[478285]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	34.9	cm2	PMID[478285]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	27.0	%	PMID[478285]

☑ 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 NPC292794 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	419
0.1-0.2	2114
0.2-0.3	4811
0.3-0.4	11051
0.4-0.5	7261
0.5-0.6	4191
0.6-0.7	5820
0.7-0.8	5853
0.8-0.85	1119
0.85-0.9	57
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9167	High Similarity	NPC290304
0.9167	High Similarity	NPC236327
0.8895	High Similarity	NPC183843
0.8817	High Similarity	NPC211309
0.8802	High Similarity	NPC110257
0.8795	High Similarity	NPC65746
0.875	High Similarity	NPC291110
0.8713	High Similarity	NPC157522
0.8713	High Similarity	NPC475964
0.869	High Similarity	NPC133065
0.8683	High Similarity	NPC162668
0.8663	High Similarity	NPC277510
0.8639	High Similarity	NPC39306
0.8631	High Similarity	NPC469575
0.8606	High Similarity	NPC18954
0.8605	High Similarity	NPC307286
0.8605	High Similarity	NPC260263
0.858	High Similarity	NPC470178
0.8571	High Similarity	NPC188486
0.8571	High Similarity	NPC260640
0.8571	High Similarity	NPC295009
0.8563	High Similarity	NPC196879
0.8563	High Similarity	NPC16935
0.8547	High Similarity	NPC28042
0.8547	High Similarity	NPC281835
0.8538	High Similarity	NPC247973
0.8529	High Similarity	NPC326520
0.8521	High Similarity	NPC84515
0.8521	High Similarity	NPC312056
0.8521	High Similarity	NPC238995
0.8521	High Similarity	NPC215612
0.8512	High Similarity	NPC285973
0.8512	High Similarity	NPC225624
0.8506	High Similarity	NPC66804
0.8503	High Similarity	NPC167595
0.85	High Similarity	NPC60848
0.8497	Intermediate Similarity	NPC178737
0.8488	Intermediate Similarity	NPC163130
0.8488	Intermediate Similarity	NPC165979
0.8485	Intermediate Similarity	NPC20337
0.848	Intermediate Similarity	NPC170245
0.8475	Intermediate Similarity	NPC471842
0.8471	Intermediate Similarity	NPC475985
0.8471	Intermediate Similarity	NPC1755
0.8471	Intermediate Similarity	NPC1706
0.8471	Intermediate Similarity	NPC39305
0.8471	Intermediate Similarity	NPC59295
0.8471	Intermediate Similarity	NPC263092
0.8466	Intermediate Similarity	NPC329161
0.8466	Intermediate Similarity	NPC240887
0.8466	Intermediate Similarity	NPC212290
0.8466	Intermediate Similarity	NPC470091
0.8452	Intermediate Similarity	NPC215375
0.8452	Intermediate Similarity	NPC62518
0.8448	Intermediate Similarity	NPC72455
0.8448	Intermediate Similarity	NPC233956
0.8448	Intermediate Similarity	NPC30550
0.8443	Intermediate Similarity	NPC45131
0.8439	Intermediate Similarity	NPC131866
0.8436	Intermediate Similarity	NPC174486
0.843	Intermediate Similarity	NPC86477
0.843	Intermediate Similarity	NPC42892
0.8424	Intermediate Similarity	NPC288316
0.8424	Intermediate Similarity	NPC171010
0.8421	Intermediate Similarity	NPC37183
0.8421	Intermediate Similarity	NPC187923
0.8421	Intermediate Similarity	NPC45449
0.8418	Intermediate Similarity	NPC97523
0.8412	Intermediate Similarity	NPC76687
0.8412	Intermediate Similarity	NPC294965
0.8412	Intermediate Similarity	NPC81679
0.8402	Intermediate Similarity	NPC14353
0.8402	Intermediate Similarity	NPC84571
0.8402	Intermediate Similarity	NPC228785
0.8402	Intermediate Similarity	NPC56085
0.84	Intermediate Similarity	NPC289244
0.84	Intermediate Similarity	NPC139350
0.8393	Intermediate Similarity	NPC474990
0.8393	Intermediate Similarity	NPC300727
0.8393	Intermediate Similarity	NPC241904
0.8391	Intermediate Similarity	NPC223375
0.8391	Intermediate Similarity	NPC471688
0.8391	Intermediate Similarity	NPC475825
0.8391	Intermediate Similarity	NPC158226
0.8383	Intermediate Similarity	NPC472048
0.8382	Intermediate Similarity	NPC41853
0.8382	Intermediate Similarity	NPC471287
0.8382	Intermediate Similarity	NPC183036
0.8382	Intermediate Similarity	NPC247136
0.8373	Intermediate Similarity	NPC38469
0.8373	Intermediate Similarity	NPC39007
0.8373	Intermediate Similarity	NPC161277
0.8373	Intermediate Similarity	NPC101996
0.8373	Intermediate Similarity	NPC125300
0.8372	Intermediate Similarity	NPC29160
0.8372	Intermediate Similarity	NPC277480
0.8372	Intermediate Similarity	NPC472452
0.8371	Intermediate Similarity	NPC228209
0.8363	Intermediate Similarity	NPC7483
0.8363	Intermediate Similarity	NPC208120
0.8363	Intermediate Similarity	NPC173587
0.8363	Intermediate Similarity	NPC101769
0.8363	Intermediate Similarity	NPC270837
0.8363	Intermediate Similarity	NPC327809
0.8363	Intermediate Similarity	NPC236132
0.8363	Intermediate Similarity	NPC475055
0.8353	Intermediate Similarity	NPC61010
0.8353	Intermediate Similarity	NPC40491
0.8353	Intermediate Similarity	NPC311740
0.8353	Intermediate Similarity	NPC269117
0.8353	Intermediate Similarity	NPC278052
0.8352	Intermediate Similarity	NPC196771
0.8352	Intermediate Similarity	NPC24258
0.8352	Intermediate Similarity	NPC257714
0.8352	Intermediate Similarity	NPC471841
0.8352	Intermediate Similarity	NPC156635
0.8343	Intermediate Similarity	NPC45846
0.8343	Intermediate Similarity	NPC98776
0.8343	Intermediate Similarity	NPC100123
0.8343	Intermediate Similarity	NPC261471
0.8343	Intermediate Similarity	NPC476242
0.8343	Intermediate Similarity	NPC310794
0.8343	Intermediate Similarity	NPC295436
0.8343	Intermediate Similarity	NPC37606
0.8333	Intermediate Similarity	NPC274730
0.8333	Intermediate Similarity	NPC78830
0.8333	Intermediate Similarity	NPC239440
0.8333	Intermediate Similarity	NPC474434
0.8333	Intermediate Similarity	NPC224462
0.8333	Intermediate Similarity	NPC73703
0.8333	Intermediate Similarity	NPC212748
0.8333	Intermediate Similarity	NPC218533
0.8333	Intermediate Similarity	NPC20543
0.8333	Intermediate Similarity	NPC10576
0.8333	Intermediate Similarity	NPC1827
0.8324	Intermediate Similarity	NPC167479
0.8324	Intermediate Similarity	NPC76482
0.8324	Intermediate Similarity	NPC95715
0.8324	Intermediate Similarity	NPC50394
0.8324	Intermediate Similarity	NPC234331
0.8324	Intermediate Similarity	NPC471288
0.8323	Intermediate Similarity	NPC244371
0.8323	Intermediate Similarity	NPC88645
0.8323	Intermediate Similarity	NPC167091
0.8323	Intermediate Similarity	NPC206238
0.8323	Intermediate Similarity	NPC271779
0.8323	Intermediate Similarity	NPC292214
0.8314	Intermediate Similarity	NPC473286
0.8314	Intermediate Similarity	NPC36320
0.8314	Intermediate Similarity	NPC300053
0.8314	Intermediate Similarity	NPC146584
0.8314	Intermediate Similarity	NPC29411
0.8314	Intermediate Similarity	NPC21016
0.8314	Intermediate Similarity	NPC102372
0.8313	Intermediate Similarity	NPC202157
0.8306	Intermediate Similarity	NPC314020
0.8305	Intermediate Similarity	NPC67302
0.8305	Intermediate Similarity	NPC23553
0.8305	Intermediate Similarity	NPC77179
0.8295	Intermediate Similarity	NPC287243
0.8295	Intermediate Similarity	NPC472607
0.8295	Intermediate Similarity	NPC227906
0.8295	Intermediate Similarity	NPC146803
0.8294	Intermediate Similarity	NPC200594
0.8294	Intermediate Similarity	NPC475886
0.8294	Intermediate Similarity	NPC320359
0.8294	Intermediate Similarity	NPC474287
0.8293	Intermediate Similarity	NPC251188
0.8286	Intermediate Similarity	NPC230619
0.8286	Intermediate Similarity	NPC205076
0.8286	Intermediate Similarity	NPC48773
0.8286	Intermediate Similarity	NPC307518
0.8286	Intermediate Similarity	NPC174700
0.8286	Intermediate Similarity	NPC54098
0.8284	Intermediate Similarity	NPC99597
0.8284	Intermediate Similarity	NPC469584
0.8284	Intermediate Similarity	NPC210084
0.8284	Intermediate Similarity	NPC262286
0.8284	Intermediate Similarity	NPC217677
0.8284	Intermediate Similarity	NPC165977
0.8284	Intermediate Similarity	NPC36852
0.8284	Intermediate Similarity	NPC179732
0.8276	Intermediate Similarity	NPC26568
0.8276	Intermediate Similarity	NPC99613
0.8276	Intermediate Similarity	NPC49487
0.8276	Intermediate Similarity	NPC210042
0.8276	Intermediate Similarity	NPC95855
0.8274	Intermediate Similarity	NPC2928
0.8268	Intermediate Similarity	NPC8927
0.8266	Intermediate Similarity	NPC53640
0.8266	Intermediate Similarity	NPC113093
0.8263	Intermediate Similarity	NPC180234
0.8263	Intermediate Similarity	NPC199100
0.8263	Intermediate Similarity	NPC120537
0.8263	Intermediate Similarity	NPC149889
0.8263	Intermediate Similarity	NPC312338
0.8258	Intermediate Similarity	NPC113446
0.8256	Intermediate Similarity	NPC152659
0.8256	Intermediate Similarity	NPC205265
0.8256	Intermediate Similarity	NPC472278

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 NPC292794 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	1137
0.2-0.3	2309
0.3-0.4	2750
0.4-0.5	1555
0.5-0.6	687
0.6-0.7	222
0.7-0.8	104
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8324	Intermediate Similarity	NPD3818	Discontinued
0.8118	Intermediate Similarity	NPD3882	Suspended
0.8107	Intermediate Similarity	NPD2801	Approved
0.8047	Intermediate Similarity	NPD1934	Approved
0.8035	Intermediate Similarity	NPD1247	Approved
0.8034	Intermediate Similarity	NPD6559	Discontinued
0.7921	Intermediate Similarity	NPD7074	Phase 3
0.7919	Intermediate Similarity	NPD6234	Discontinued
0.7895	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD5494	Approved
0.7865	Intermediate Similarity	NPD7054	Approved
0.7821	Intermediate Similarity	NPD7472	Approved
0.7816	Intermediate Similarity	NPD919	Approved
0.7791	Intermediate Similarity	NPD1465	Phase 2
0.7784	Intermediate Similarity	NPD6232	Discontinued
0.7784	Intermediate Similarity	NPD1511	Approved
0.7753	Intermediate Similarity	NPD7473	Discontinued
0.7738	Intermediate Similarity	NPD2533	Approved
0.7738	Intermediate Similarity	NPD2532	Approved
0.7738	Intermediate Similarity	NPD2534	Approved
0.7701	Intermediate Similarity	NPD4966	Approved
0.7701	Intermediate Similarity	NPD4967	Phase 2
0.7701	Intermediate Similarity	NPD4965	Approved
0.7692	Intermediate Similarity	NPD1512	Approved
0.768	Intermediate Similarity	NPD6797	Phase 2
0.7667	Intermediate Similarity	NPD5844	Phase 1
0.7657	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2800	Approved
0.7647	Intermediate Similarity	NPD920	Approved
0.764	Intermediate Similarity	NPD3926	Phase 2
0.7637	Intermediate Similarity	NPD7251	Discontinued
0.7611	Intermediate Similarity	NPD7228	Approved
0.76	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD6166	Phase 2
0.7598	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD7808	Phase 3
0.7543	Intermediate Similarity	NPD3817	Phase 2
0.754	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD37	Approved
0.7528	Intermediate Similarity	NPD7199	Phase 2
0.7486	Intermediate Similarity	NPD7819	Suspended
0.7473	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD3749	Approved
0.7444	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD6959	Discontinued
0.7427	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1549	Phase 2
0.7381	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7075	Discontinued
0.7341	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD8434	Phase 2
0.7326	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD3751	Discontinued
0.7321	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2344	Approved
0.7314	Intermediate Similarity	NPD6599	Discontinued
0.7314	Intermediate Similarity	NPD4380	Phase 2
0.731	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1510	Phase 2
0.7289	Intermediate Similarity	NPD1607	Approved
0.7288	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD943	Approved
0.7273	Intermediate Similarity	NPD1240	Approved
0.7267	Intermediate Similarity	NPD6799	Approved
0.7262	Intermediate Similarity	NPD1551	Phase 2
0.7235	Intermediate Similarity	NPD1243	Approved
0.7232	Intermediate Similarity	NPD6801	Discontinued
0.7229	Intermediate Similarity	NPD230	Phase 1
0.7222	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD5710	Approved
0.7198	Intermediate Similarity	NPD5711	Approved
0.7194	Intermediate Similarity	NPD6778	Approved
0.7194	Intermediate Similarity	NPD6779	Approved
0.7194	Intermediate Similarity	NPD6776	Approved
0.7194	Intermediate Similarity	NPD6777	Approved
0.7194	Intermediate Similarity	NPD6782	Approved
0.7194	Intermediate Similarity	NPD6780	Approved
0.7194	Intermediate Similarity	NPD6781	Approved
0.7168	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7240	Approved
0.7159	Intermediate Similarity	NPD3226	Approved
0.7151	Intermediate Similarity	NPD2309	Approved
0.7151	Intermediate Similarity	NPD5402	Approved
0.7143	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD1471	Phase 3
0.7102	Intermediate Similarity	NPD1653	Approved
0.7101	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3750	Approved
0.709	Intermediate Similarity	NPD8312	Approved
0.709	Intermediate Similarity	NPD8313	Approved
0.7085	Intermediate Similarity	NPD7435	Discontinued
0.7079	Intermediate Similarity	NPD7411	Suspended
0.7079	Intermediate Similarity	NPD8151	Discontinued
0.7059	Intermediate Similarity	NPD2796	Approved
0.7059	Intermediate Similarity	NPD2935	Discontinued
0.7056	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD6534	Approved
0.7026	Intermediate Similarity	NPD6535	Approved
0.7024	Intermediate Similarity	NPD447	Suspended
0.7018	Intermediate Similarity	NPD2346	Discontinued
0.7018	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3787	Discontinued
0.7	Intermediate Similarity	NPD7697	Approved
0.7	Intermediate Similarity	NPD7698	Approved
0.7	Intermediate Similarity	NPD7696	Phase 3
0.6982	Remote Similarity	NPD6651	Approved
0.697	Remote Similarity	NPD9494	Approved
0.6965	Remote Similarity	NPD7870	Phase 2
0.6965	Remote Similarity	NPD7871	Phase 2
0.6946	Remote Similarity	NPD7701	Phase 2
0.6946	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7768	Phase 2
0.6919	Remote Similarity	NPD7700	Phase 2
0.6919	Remote Similarity	NPD7699	Phase 2
0.6897	Remote Similarity	NPD4628	Phase 3
0.6895	Remote Similarity	NPD7685	Pre-registration
0.6884	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7874	Approved
0.6867	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD6823	Phase 2
0.6864	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1613	Approved
0.6845	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7801	Approved
0.6845	Remote Similarity	NPD7783	Phase 2
0.6842	Remote Similarity	NPD5953	Discontinued
0.6832	Remote Similarity	NPD7680	Approved
0.6826	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7286	Phase 2
0.6824	Remote Similarity	NPD1933	Approved
0.6813	Remote Similarity	NPD5760	Phase 2
0.6813	Remote Similarity	NPD5761	Phase 2
0.6802	Remote Similarity	NPD6212	Phase 3
0.6802	Remote Similarity	NPD6213	Phase 3
0.6802	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3748	Approved
0.6782	Remote Similarity	NPD5005	Approved
0.6782	Remote Similarity	NPD5006	Approved
0.676	Remote Similarity	NPD5403	Approved
0.6743	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD6674	Discontinued
0.6742	Remote Similarity	NPD5401	Approved
0.6735	Remote Similarity	NPD4287	Approved
0.6729	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7907	Approved
0.6705	Remote Similarity	NPD2799	Discontinued
0.6698	Remote Similarity	NPD4665	Approved
0.6698	Remote Similarity	NPD4111	Phase 1
0.6686	Remote Similarity	NPD3027	Phase 3
0.6685	Remote Similarity	NPD2296	Approved
0.6685	Remote Similarity	NPD7390	Discontinued
0.6685	Remote Similarity	NPD7458	Discontinued
0.6684	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD4420	Approved
0.6667	Remote Similarity	NPD6100	Approved
0.6649	Remote Similarity	NPD7229	Phase 3
0.6647	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2313	Discontinued
0.6647	Remote Similarity	NPD1470	Approved
0.6633	Remote Similarity	NPD8150	Discontinued
0.6614	Remote Similarity	NPD5242	Approved
0.661	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD8404	Phase 2
0.6602	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD2403	Approved
0.6573	Remote Similarity	NPD6190	Approved
0.657	Remote Similarity	NPD7584	Approved
0.6566	Remote Similarity	NPD9269	Phase 2
0.6558	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7028	Phase 2
0.6553	Remote Similarity	NPD8320	Phase 1
0.6553	Remote Similarity	NPD8319	Approved
0.6548	Remote Similarity	NPD1203	Approved
0.6546	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD1729	Discontinued
0.6527	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD3705	Approved
0.6486	Remote Similarity	NPD6280	Approved
0.6486	Remote Similarity	NPD6279	Approved
0.6484	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD8059	Phase 3
0.6479	Remote Similarity	NPD7047	Phase 3
0.6474	Remote Similarity	NPD6808	Phase 2
0.6453	Remote Similarity	NPD3764	Approved
0.6437	Remote Similarity	NPD1899	Clinical (unspecified phase)

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