NPASS Compound

Structure

CID3898 OpenBabel06191715322D 35 38 0 0 0 0 0 0 0 0999 V2000 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1340 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8660 -2.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3660 1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3660 -1.8301 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8660 -0.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3660 -1.8301 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3660 -0.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3660 -0.0981 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 -1.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8660 -0.9641 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3660 -0.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8660 0.7679 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 -3.8660 -0.9641 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8660 0.7679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3660 1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3660 -1.8301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3660 1.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 1.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 28 1 0 0 0 0 3 33 1 0 0 0 0 4 34 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 7 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 16 2 0 0 0 0 10 17 2 0 0 0 0 11 18 2 0 0 0 0 12 19 2 0 0 0 0 13 20 1 0 0 0 0 13 22 2 0 0 0 0 14 21 1 0 0 0 0 14 28 1 0 0 0 0 15 28 1 0 0 0 0 15 35 1 0 0 0 0 16 19 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 26 1 0 0 0 0 20 26 2 0 0 0 0 20 27 1 0 0 0 0 21 23 1 0 0 0 0 21 25 2 0 0 0 0 22 33 1 0 0 0 0 23 29 2 0 0 0 0 24 25 1 0 0 0 0 24 30 2 0 0 0 0 25 31 1 0 0 0 0 26 34 1 0 0 0 0 27 32 2 0 0 0 0 27 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.17
Volume:	488.512
LogP:	4.891
LogD:	3.521
LogS:	-6.183
# Rotatable Bonds:	8
TPSA:	95.97
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.278
Synthetic Accessibility Score:	3.235
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.865
MDCK Permeability:	2.559476524766069e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.054

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	99.22010040283203%
Volume Distribution (VD):	0.377
Pgp-substrate:	1.348573088645935%

ADMET: Metabolism

CYP1A2-inhibitor:	0.462
CYP1A2-substrate:	0.867
CYP2C19-inhibitor:	0.932
CYP2C19-substrate:	0.186
CYP2C9-inhibitor:	0.946
CYP2C9-substrate:	0.891
CYP2D6-inhibitor:	0.313
CYP2D6-substrate:	0.721
CYP3A4-inhibitor:	0.937
CYP3A4-substrate:	0.424

ADMET: Excretion

Clearance (CL):	3.55
Half-life (T1/2):	0.043

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.924
AMES Toxicity:	0.572
Rat Oral Acute Toxicity:	0.448
Maximum Recommended Daily Dose:	0.491
Skin Sensitization:	0.042
Carcinogencity:	0.681
Eye Corrosion:	0.003
Eye Irritation:	0.065
Respiratory Toxicity:	0.031

Download Data

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

Natural Product: NPC3898

Natural Product ID:	NPC3898
*Common Name:**	DSDQYPOXSDSSCO-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DSDQYPOXSDSSCO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H26O7/c1-28(2,14-21-23(29)17-10-6-7-11-18(17)24(30)25(21)31)15-35-27(32)20-13-22(33-3)16-9-5-8-12-19(16)26(20)34-4/h5-13,31H,14-15H2,1-4H3
SMILES:	COc1c(cc(c2c1cccc2)OC)C(=O)OCC(CC1=C(O)C(=O)c2c(C1=O)cccc2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL184182
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0001871] Naphthalenecarboxylic acids and derivatives [CHEMONTID:0002421] Naphthalenecarboxylic acids

*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
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8463799]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8792629]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9214738]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11678	Aeonium cuneatum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13891	Scolytus multistriatus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11855	Streptomyces xanthocidicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14480	Tornabea scutellifera	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12707	Lithospermum canescens	Species	Boraginaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	350.0	nM	PMID[503208]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	1090.0	nM	PMID[503208]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	970.0	nM	PMID[503208]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	32700.0	nM	PMID[503208]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	350.0	nM	PMID[503209]

☑ 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 NPC3898 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	367
0.1-0.2	1554
0.2-0.3	3334
0.3-0.4	7906
0.4-0.5	10862
0.5-0.6	4542
0.6-0.7	6874
0.7-0.8	6935
0.8-0.85	292
0.85-0.9	27
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9866	High Similarity	NPC67197
0.8816	High Similarity	NPC300540
0.8733	High Similarity	NPC149780
0.8693	High Similarity	NPC211565
0.8693	High Similarity	NPC60389
0.8675	High Similarity	NPC69755
0.8636	High Similarity	NPC478163
0.8625	High Similarity	NPC284495
0.8609	High Similarity	NPC124365
0.8608	High Similarity	NPC66029
0.8581	High Similarity	NPC474107
0.8571	High Similarity	NPC147250
0.8562	High Similarity	NPC89664
0.8562	High Similarity	NPC274085
0.8553	High Similarity	NPC474360
0.8544	High Similarity	NPC477691
0.8506	High Similarity	NPC478019
0.8497	Intermediate Similarity	NPC53016
0.8497	Intermediate Similarity	NPC476473
0.8494	Intermediate Similarity	NPC477836
0.8494	Intermediate Similarity	NPC473113
0.8481	Intermediate Similarity	NPC477690
0.8477	Intermediate Similarity	NPC477408
0.8477	Intermediate Similarity	NPC470407
0.8471	Intermediate Similarity	NPC205766
0.8467	Intermediate Similarity	NPC471542
0.8462	Intermediate Similarity	NPC472841
0.8457	Intermediate Similarity	NPC24761
0.8456	Intermediate Similarity	NPC281513
0.8456	Intermediate Similarity	NPC22222
0.8447	Intermediate Similarity	NPC324736
0.8438	Intermediate Similarity	NPC279605
0.8438	Intermediate Similarity	NPC469507
0.8435	Intermediate Similarity	NPC205360
0.8431	Intermediate Similarity	NPC474300
0.8424	Intermediate Similarity	NPC76647
0.8415	Intermediate Similarity	NPC71390
0.8415	Intermediate Similarity	NPC26386
0.8411	Intermediate Similarity	NPC475104
0.8397	Intermediate Similarity	NPC119767
0.8397	Intermediate Similarity	NPC478018
0.8393	Intermediate Similarity	NPC186800
0.8377	Intermediate Similarity	NPC163948
0.8377	Intermediate Similarity	NPC66593
0.8375	Intermediate Similarity	NPC478161
0.8375	Intermediate Similarity	NPC226656
0.8375	Intermediate Similarity	NPC478159
0.8375	Intermediate Similarity	NPC66508
0.8365	Intermediate Similarity	NPC175978
0.8365	Intermediate Similarity	NPC281272
0.8364	Intermediate Similarity	NPC477835
0.8355	Intermediate Similarity	NPC1268
0.8355	Intermediate Similarity	NPC476191
0.8354	Intermediate Similarity	NPC294646
0.8344	Intermediate Similarity	NPC472261
0.8344	Intermediate Similarity	NPC186647
0.8344	Intermediate Similarity	NPC301341
0.8333	Intermediate Similarity	NPC477692
0.8323	Intermediate Similarity	NPC221992
0.8323	Intermediate Similarity	NPC477409
0.8322	Intermediate Similarity	NPC470406
0.8313	Intermediate Similarity	NPC473094
0.8302	Intermediate Similarity	NPC39819
0.8302	Intermediate Similarity	NPC230848
0.8299	Intermediate Similarity	NPC57552
0.8291	Intermediate Similarity	NPC70764
0.8284	Intermediate Similarity	NPC470667
0.8282	Intermediate Similarity	NPC476506
0.8278	Intermediate Similarity	NPC155211
0.8278	Intermediate Similarity	NPC232996
0.8278	Intermediate Similarity	NPC471670
0.8272	Intermediate Similarity	NPC317580
0.8272	Intermediate Similarity	NPC263483
0.8269	Intermediate Similarity	NPC474630
0.8269	Intermediate Similarity	NPC49282
0.8267	Intermediate Similarity	NPC27394
0.8267	Intermediate Similarity	NPC1249
0.8263	Intermediate Similarity	NPC473095
0.8263	Intermediate Similarity	NPC473096
0.8261	Intermediate Similarity	NPC318270
0.8253	Intermediate Similarity	NPC30027
0.825	Intermediate Similarity	NPC24232
0.825	Intermediate Similarity	NPC164912
0.825	Intermediate Similarity	NPC154683
0.825	Intermediate Similarity	NPC44606
0.825	Intermediate Similarity	NPC40356
0.8247	Intermediate Similarity	NPC283292
0.8247	Intermediate Similarity	NPC257003
0.8239	Intermediate Similarity	NPC470568
0.8239	Intermediate Similarity	NPC290954
0.8239	Intermediate Similarity	NPC147735
0.8239	Intermediate Similarity	NPC144010
0.8239	Intermediate Similarity	NPC255641
0.8239	Intermediate Similarity	NPC474660
0.8235	Intermediate Similarity	NPC256463
0.8235	Intermediate Similarity	NPC471602
0.8235	Intermediate Similarity	NPC306835
0.8235	Intermediate Similarity	NPC29771
0.8235	Intermediate Similarity	NPC111422
0.8235	Intermediate Similarity	NPC299405
0.8235	Intermediate Similarity	NPC476477
0.8235	Intermediate Similarity	NPC216312
0.8228	Intermediate Similarity	NPC172329
0.8228	Intermediate Similarity	NPC2569
0.8224	Intermediate Similarity	NPC245923
0.8224	Intermediate Similarity	NPC284184
0.8221	Intermediate Similarity	NPC326084
0.821	Intermediate Similarity	NPC146211
0.8205	Intermediate Similarity	NPC475813
0.8204	Intermediate Similarity	NPC234331
0.8204	Intermediate Similarity	NPC473945
0.8204	Intermediate Similarity	NPC472660
0.8199	Intermediate Similarity	NPC218870
0.8199	Intermediate Similarity	NPC474824
0.8199	Intermediate Similarity	NPC474622
0.8199	Intermediate Similarity	NPC470408
0.8199	Intermediate Similarity	NPC135522
0.8199	Intermediate Similarity	NPC182921
0.8199	Intermediate Similarity	NPC474621
0.8193	Intermediate Similarity	NPC178281
0.8193	Intermediate Similarity	NPC314653
0.8193	Intermediate Similarity	NPC316262
0.8187	Intermediate Similarity	NPC118427
0.8187	Intermediate Similarity	NPC145830
0.8187	Intermediate Similarity	NPC470569
0.8182	Intermediate Similarity	NPC220496
0.8182	Intermediate Similarity	NPC37992
0.8182	Intermediate Similarity	NPC147542
0.8182	Intermediate Similarity	NPC42262
0.8182	Intermediate Similarity	NPC241349
0.8182	Intermediate Similarity	NPC327916
0.8182	Intermediate Similarity	NPC32749
0.8176	Intermediate Similarity	NPC472298
0.8176	Intermediate Similarity	NPC80370
0.8171	Intermediate Similarity	NPC470342
0.8171	Intermediate Similarity	NPC185617
0.8171	Intermediate Similarity	NPC313368
0.8171	Intermediate Similarity	NPC472060
0.8171	Intermediate Similarity	NPC472052
0.8171	Intermediate Similarity	NPC475449
0.8166	Intermediate Similarity	NPC478002
0.8165	Intermediate Similarity	NPC126767
0.8165	Intermediate Similarity	NPC289042
0.8165	Intermediate Similarity	NPC118027
0.8165	Intermediate Similarity	NPC190648
0.8165	Intermediate Similarity	NPC312929
0.8165	Intermediate Similarity	NPC56433
0.8165	Intermediate Similarity	NPC245584
0.8163	Intermediate Similarity	NPC45537
0.816	Intermediate Similarity	NPC44199
0.816	Intermediate Similarity	NPC201127
0.8158	Intermediate Similarity	NPC474813
0.8158	Intermediate Similarity	NPC141934
0.8158	Intermediate Similarity	NPC472308
0.8158	Intermediate Similarity	NPC475549
0.8155	Intermediate Similarity	NPC49487
0.8155	Intermediate Similarity	NPC99613
0.8153	Intermediate Similarity	NPC473951
0.8153	Intermediate Similarity	NPC47152
0.8153	Intermediate Similarity	NPC478160
0.8144	Intermediate Similarity	NPC125465
0.8144	Intermediate Similarity	NPC29160
0.8141	Intermediate Similarity	NPC469885
0.8141	Intermediate Similarity	NPC167663
0.8141	Intermediate Similarity	NPC478164
0.8137	Intermediate Similarity	NPC474534
0.8137	Intermediate Similarity	NPC474533
0.8133	Intermediate Similarity	NPC477689
0.8133	Intermediate Similarity	NPC474340
0.8133	Intermediate Similarity	NPC17432
0.8129	Intermediate Similarity	NPC471444
0.8129	Intermediate Similarity	NPC102053
0.8125	Intermediate Similarity	NPC473466
0.8125	Intermediate Similarity	NPC119929
0.8125	Intermediate Similarity	NPC315520
0.8121	Intermediate Similarity	NPC31539
0.8118	Intermediate Similarity	NPC85368
0.8118	Intermediate Similarity	NPC229051
0.8118	Intermediate Similarity	NPC131862
0.8117	Intermediate Similarity	NPC295339
0.8113	Intermediate Similarity	NPC95526
0.8113	Intermediate Similarity	NPC5537
0.811	Intermediate Similarity	NPC186113
0.811	Intermediate Similarity	NPC472299
0.811	Intermediate Similarity	NPC471541
0.811	Intermediate Similarity	NPC228654
0.8107	Intermediate Similarity	NPC313304
0.8101	Intermediate Similarity	NPC314437
0.8101	Intermediate Similarity	NPC301949
0.8101	Intermediate Similarity	NPC225173
0.8101	Intermediate Similarity	NPC163846
0.8101	Intermediate Similarity	NPC470570
0.8098	Intermediate Similarity	NPC472453
0.8098	Intermediate Similarity	NPC474861
0.8095	Intermediate Similarity	NPC324522
0.8095	Intermediate Similarity	NPC469521
0.8095	Intermediate Similarity	NPC470341
0.8095	Intermediate Similarity	NPC472058
0.8095	Intermediate Similarity	NPC105414
0.8095	Intermediate Similarity	NPC234497

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 NPC3898 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	981
0.2-0.3	1412
0.3-0.4	2471
0.4-0.5	2177
0.5-0.6	1161
0.6-0.7	438
0.7-0.8	173
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8533	High Similarity	NPD2346	Discontinued
0.8408	Intermediate Similarity	NPD3226	Approved
0.8344	Intermediate Similarity	NPD2935	Discontinued
0.8291	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD7003	Approved
0.8182	Intermediate Similarity	NPD6232	Discontinued
0.8144	Intermediate Similarity	NPD7473	Discontinued
0.8114	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD7819	Suspended
0.8047	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD2313	Discontinued
0.8	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD2799	Discontinued
0.7904	Intermediate Similarity	NPD6959	Discontinued
0.7901	Intermediate Similarity	NPD6599	Discontinued
0.7871	Intermediate Similarity	NPD5404	Approved
0.7871	Intermediate Similarity	NPD5406	Approved
0.7871	Intermediate Similarity	NPD5408	Approved
0.7871	Intermediate Similarity	NPD5405	Approved
0.7853	Intermediate Similarity	NPD7411	Suspended
0.784	Intermediate Similarity	NPD7458	Discontinued
0.7821	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD5402	Approved
0.7812	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2533	Approved
0.7812	Intermediate Similarity	NPD2532	Approved
0.7812	Intermediate Similarity	NPD2534	Approved
0.7784	Intermediate Similarity	NPD8150	Discontinued
0.7771	Intermediate Similarity	NPD7768	Phase 2
0.7764	Intermediate Similarity	NPD6273	Approved
0.7758	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD8312	Approved
0.7714	Intermediate Similarity	NPD8313	Approved
0.7702	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD7435	Discontinued
0.7661	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6832	Phase 2
0.7619	Intermediate Similarity	NPD7075	Discontinued
0.7619	Intermediate Similarity	NPD3749	Approved
0.7616	Intermediate Similarity	NPD2798	Approved
0.7613	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6777	Approved
0.7609	Intermediate Similarity	NPD6779	Approved
0.7609	Intermediate Similarity	NPD6778	Approved
0.7609	Intermediate Similarity	NPD6776	Approved
0.7609	Intermediate Similarity	NPD6780	Approved
0.7609	Intermediate Similarity	NPD6781	Approved
0.7609	Intermediate Similarity	NPD6782	Approved
0.76	Intermediate Similarity	NPD1283	Approved
0.758	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7177	Discontinued
0.7562	Intermediate Similarity	NPD3750	Approved
0.755	Intermediate Similarity	NPD1470	Approved
0.7548	Intermediate Similarity	NPD2979	Phase 3
0.754	Intermediate Similarity	NPD7870	Phase 2
0.754	Intermediate Similarity	NPD7871	Phase 2
0.7531	Intermediate Similarity	NPD7390	Discontinued
0.7531	Intermediate Similarity	NPD6799	Approved
0.7529	Intermediate Similarity	NPD5494	Approved
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3817	Phase 2
0.7487	Intermediate Similarity	NPD7696	Phase 3
0.7487	Intermediate Similarity	NPD7697	Approved
0.7487	Intermediate Similarity	NPD7698	Approved
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7485	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6801	Discontinued
0.7484	Intermediate Similarity	NPD1471	Phase 3
0.7484	Intermediate Similarity	NPD2344	Approved
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.747	Intermediate Similarity	NPD4380	Phase 2
0.7468	Intermediate Similarity	NPD4308	Phase 3
0.7468	Intermediate Similarity	NPD7008	Discontinued
0.7468	Intermediate Similarity	NPD3748	Approved
0.7453	Intermediate Similarity	NPD4628	Phase 3
0.7453	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7874	Approved
0.7434	Intermediate Similarity	NPD1203	Approved
0.7421	Intermediate Similarity	NPD1551	Phase 2
0.7419	Intermediate Similarity	NPD3268	Approved
0.7419	Intermediate Similarity	NPD411	Approved
0.7401	Intermediate Similarity	NPD6559	Discontinued
0.74	Intermediate Similarity	NPD1611	Approved
0.74	Intermediate Similarity	NPD1281	Approved
0.7394	Intermediate Similarity	NPD5403	Approved
0.7389	Intermediate Similarity	NPD447	Suspended
0.7381	Intermediate Similarity	NPD6844	Discontinued
0.7378	Intermediate Similarity	NPD5401	Approved
0.7372	Intermediate Similarity	NPD6233	Phase 2
0.7362	Intermediate Similarity	NPD7236	Approved
0.7358	Intermediate Similarity	NPD1510	Phase 2
0.7356	Intermediate Similarity	NPD6166	Phase 2
0.7356	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD9717	Approved
0.7351	Intermediate Similarity	NPD3972	Approved
0.7346	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1607	Approved
0.7337	Intermediate Similarity	NPD6534	Approved
0.7337	Intermediate Similarity	NPD2801	Approved
0.7337	Intermediate Similarity	NPD6535	Approved
0.733	Intermediate Similarity	NPD7701	Phase 2
0.7325	Intermediate Similarity	NPD4307	Phase 2
0.732	Intermediate Similarity	NPD2797	Approved
0.7315	Intermediate Similarity	NPD1651	Approved
0.7315	Intermediate Similarity	NPD5691	Approved
0.7312	Intermediate Similarity	NPD2438	Suspended
0.7312	Intermediate Similarity	NPD2796	Approved
0.7308	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6798	Discontinued
0.7301	Intermediate Similarity	NPD2309	Approved
0.7289	Intermediate Similarity	NPD920	Approved
0.7285	Intermediate Similarity	NPD1201	Approved
0.7285	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4626	Approved
0.7263	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD3882	Suspended
0.7246	Intermediate Similarity	NPD7239	Suspended
0.7241	Intermediate Similarity	NPD5711	Approved
0.7241	Intermediate Similarity	NPD3787	Discontinued
0.7241	Intermediate Similarity	NPD7229	Phase 3
0.7241	Intermediate Similarity	NPD5710	Approved
0.7239	Intermediate Similarity	NPD8166	Discontinued
0.7222	Intermediate Similarity	NPD1549	Phase 2
0.7219	Intermediate Similarity	NPD5889	Approved
0.7219	Intermediate Similarity	NPD7699	Phase 2
0.7219	Intermediate Similarity	NPD5890	Approved
0.7219	Intermediate Similarity	NPD7700	Phase 2
0.7216	Intermediate Similarity	NPD7801	Approved
0.7215	Intermediate Similarity	NPD4060	Phase 1
0.7215	Intermediate Similarity	NPD1240	Approved
0.7208	Intermediate Similarity	NPD3267	Approved
0.7208	Intermediate Similarity	NPD3266	Approved
0.7205	Intermediate Similarity	NPD2531	Phase 2
0.7202	Intermediate Similarity	NPD8151	Discontinued
0.7197	Intermediate Similarity	NPD3764	Approved
0.7189	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD6213	Phase 3
0.7189	Intermediate Similarity	NPD6212	Phase 3
0.7184	Intermediate Similarity	NPD1247	Approved
0.7178	Intermediate Similarity	NPD2800	Approved
0.7176	Intermediate Similarity	NPD1934	Approved
0.7175	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1933	Approved
0.7169	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD919	Approved
0.7161	Intermediate Similarity	NPD1019	Discontinued
0.716	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6823	Phase 2
0.7152	Intermediate Similarity	NPD8032	Phase 2
0.7152	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3300	Phase 2
0.7152	Intermediate Similarity	NPD1778	Approved
0.7151	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7095	Approved
0.7128	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7783	Phase 2
0.7126	Intermediate Similarity	NPD1512	Approved
0.7114	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD9493	Approved
0.711	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3496	Discontinued
0.7102	Intermediate Similarity	NPD3926	Phase 2
0.7099	Intermediate Similarity	NPD6100	Approved
0.7099	Intermediate Similarity	NPD4476	Approved
0.7099	Intermediate Similarity	NPD6099	Approved
0.7099	Intermediate Similarity	NPD4477	Approved
0.7097	Intermediate Similarity	NPD1164	Approved
0.7095	Intermediate Similarity	NPD5951	Approved
0.7093	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD8285	Discontinued
0.7083	Intermediate Similarity	NPD8320	Phase 1
0.7083	Intermediate Similarity	NPD8319	Approved
0.7073	Intermediate Similarity	NPD1243	Approved
0.7069	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6355	Discontinued
0.7059	Intermediate Similarity	NPD6585	Discontinued
0.7056	Intermediate Similarity	NPD5953	Discontinued
0.7055	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6808	Phase 2
0.7035	Intermediate Similarity	NPD1465	Phase 2
0.7032	Intermediate Similarity	NPD1876	Approved
0.7013	Intermediate Similarity	NPD1608	Approved
0.7006	Intermediate Similarity	NPD1511	Approved
0.7	Intermediate Similarity	NPD4140	Approved
0.7	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD8127	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