NPASS Compound

Structure

CID323821 OpenBabel06191716172D 35 39 0 0 1 0 0 0 0 0999 V2000 4.1043 -3.4182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4131 -3.6199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7381 -0.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6758 2.0815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3394 -2.7614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1408 -2.6307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3763 -1.1602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3115 -0.9588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3980 -2.6119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7640 -2.2583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0104 -1.5137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4932 -2.2772 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5258 -1.7707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0212 -2.2395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2166 -0.4596 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8098 -1.4479 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1191 -1.1790 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3196 -0.9588 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2851 0.0651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7330 -2.1361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8612 0.5371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7532 -1.5325 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5041 -1.5513 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0081 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8758 -0.9966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4770 -1.4367 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9017 -2.7305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1753 -0.1481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0691 1.0089 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5872 -2.6715 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7529 0.0668 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8227 1.5444 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 1.1471 -2.5052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7610 -1.1139 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 9 1 0 0 0 0 4 32 1 0 0 0 0 5 13 1 0 0 0 0 6 10 1 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 22 1 0 0 0 0 8 33 1 0 0 0 0 9 10 1 0 0 0 0 9 14 2 0 0 0 0 10 22 1 1 0 0 0 11 14 1 0 0 0 0 11 25 2 0 0 0 0 12 23 1 6 0 0 0 12 34 1 0 0 0 0 13 26 2 0 0 0 0 13 35 1 0 0 0 0 14 27 1 0 0 0 0 15 17 1 0 0 0 0 15 19 1 0 0 0 0 15 28 1 1 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 16 35 1 1 0 0 0 17 22 1 1 0 0 0 17 23 1 0 0 0 0 18 23 1 6 0 0 0 18 24 1 0 0 0 0 19 24 1 6 0 0 0 19 29 1 0 0 0 0 20 30 2 0 0 0 0 20 34 1 0 0 0 0 21 31 2 0 0 0 0 21 32 1 0 0 0 0 22 3 1 1 0 0 0 23 8 1 1 0 0 0 24 21 1 1 0 0 0 24 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.18
Volume:	464.388
LogP:	0.874
LogD:	0.371
LogS:	-4.101
# Rotatable Bonds:	5
TPSA:	162.73
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.291
Synthetic Accessibility Score:	6.488
Fsp3:	0.792
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.373
MDCK Permeability:	7.891933637438342e-05
Pgp-inhibitor:	0.982
Pgp-substrate:	0.467
Human Intestinal Absorption (HIA):	0.127
20% Bioavailability (F20%):	0.262
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.173
Plasma Protein Binding (PPB):	40.66010284423828%
Volume Distribution (VD):	0.334
Pgp-substrate:	47.55900573730469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.894
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.352
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.25
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	4.028
Half-life (T1/2):	0.472

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.368
Drug-inuced Liver Injury (DILI):	0.916
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.208
Maximum Recommended Daily Dose:	0.351
Skin Sensitization:	0.149
Carcinogencity:	0.107
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.541

Download Data

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

Natural Product: NPC323821

Natural Product ID:	NPC323821
*Common Name:**	JMNCUIIGFZOUJI-WUXZYLOCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JMNCUIIGFZOUJI-WUXZYLOCSA-N
Standard InCHI:	InChI=1S/C24H30O11/c1-5-13(26)35-16-18-23-8-33-24(18,21(31)32-4)19(29)15(28)17(23)22(3)7-11(25)14(27)9(2)10(22)6-12(23)34-20(16)30/h10,12,15-19,27-29H,5-8H2,1-4H3/t10-,12+,15+,16+,17+,18+,19-,22-,23+,24-/m0/s1
SMILES:	CCC(=O)OC1C2C34COC2(C(C(C3C5(CC(=O)C(=C(C5CC4OC1=O)C)O)C)O)O)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL143600
PubChem CID:	44361173
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/0031-9422(96)00258-0]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S1383-5769(99)00023-9]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10086989]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1512598]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15165151]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	fruit	Indonesia	n.a.	PMID[17896817]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	Vietnam	n.a.	PMID[19026551]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20050684]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[22506620]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6481366]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561896]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14948	Brucea javanica	Species	Simaroubaceae	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
EC50	2
Others	1

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1759	Cell Line	FM3A	Mus musculus	EC50	=	7000.0	nM	PMID[529810]
NPT1759	Cell Line	FM3A	Mus musculus	Ratio	=	241.0	n.a.	PMID[529810]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	29.0	nM	PMID[529810]

☑ 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 NPC323821 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	281
0.1-0.2	1797
0.2-0.3	5255
0.3-0.4	8429
0.4-0.5	11569
0.5-0.6	7124
0.6-0.7	5158
0.7-0.8	2763
0.8-0.85	202
0.85-0.9	75
0.9-0.95	35
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC268238
1.0	High Similarity	NPC45218
1.0	High Similarity	NPC143268
0.9906	High Similarity	NPC16081
0.9906	High Similarity	NPC173686
0.9633	High Similarity	NPC470777
0.9541	High Similarity	NPC17772
0.9375	High Similarity	NPC312833
0.9292	High Similarity	NPC265557
0.9292	High Similarity	NPC91693
0.9292	High Similarity	NPC105926
0.9292	High Similarity	NPC18945
0.9273	High Similarity	NPC122033
0.9273	High Similarity	NPC474654
0.9273	High Similarity	NPC470854
0.9273	High Similarity	NPC287343
0.9273	High Similarity	NPC97908
0.9211	High Similarity	NPC24651
0.9211	High Similarity	NPC476729
0.9182	High Similarity	NPC40632
0.9182	High Similarity	NPC96312
0.9182	High Similarity	NPC251236
0.9182	High Similarity	NPC328374
0.9174	High Similarity	NPC49451
0.913	High Similarity	NPC87662
0.9091	High Similarity	NPC473798
0.9018	High Similarity	NPC188667
0.9018	High Similarity	NPC297179
0.9018	High Similarity	NPC204552
0.9018	High Similarity	NPC470776
0.9	High Similarity	NPC7921
0.9	High Similarity	NPC208998
0.8972	High Similarity	NPC202524
0.8966	High Similarity	NPC477745
0.8957	High Similarity	NPC67251
0.8947	High Similarity	NPC470779
0.8947	High Similarity	NPC102822
0.8947	High Similarity	NPC477046
0.8889	High Similarity	NPC476008
0.8879	High Similarity	NPC181357
0.886	High Similarity	NPC112038
0.885	High Similarity	NPC251310
0.8839	High Similarity	NPC134869
0.8839	High Similarity	NPC207217
0.8839	High Similarity	NPC152199
0.8839	High Similarity	NPC235539
0.8829	High Similarity	NPC198539
0.8818	High Similarity	NPC146945
0.8818	High Similarity	NPC171888
0.8814	High Similarity	NPC295220
0.8814	High Similarity	NPC475636
0.8772	High Similarity	NPC469488
0.8761	High Similarity	NPC470775
0.8761	High Similarity	NPC176513
0.875	High Similarity	NPC474906
0.875	High Similarity	NPC18547
0.8739	High Similarity	NPC54614
0.8739	High Similarity	NPC474516
0.8739	High Similarity	NPC11252
0.8739	High Similarity	NPC289312
0.8739	High Similarity	NPC309096
0.8716	High Similarity	NPC293850
0.8673	High Similarity	NPC474734
0.8649	High Similarity	NPC201992
0.8636	High Similarity	NPC27814
0.8632	High Similarity	NPC227397
0.8624	High Similarity	NPC3316
0.8624	High Similarity	NPC144854
0.8611	High Similarity	NPC65523
0.8596	High Similarity	NPC470778
0.8596	High Similarity	NPC473590
0.8596	High Similarity	NPC146432
0.8584	High Similarity	NPC299849
0.8559	High Similarity	NPC470922
0.8545	High Similarity	NPC277017
0.8545	High Similarity	NPC154608
0.8545	High Similarity	NPC192813
0.8537	High Similarity	NPC262813
0.8509	High Similarity	NPC213084
0.8509	High Similarity	NPC190185
0.8509	High Similarity	NPC89929
0.85	High Similarity	NPC188291
0.8496	Intermediate Similarity	NPC51978
0.8496	Intermediate Similarity	NPC94509
0.8482	Intermediate Similarity	NPC34315
0.8468	Intermediate Similarity	NPC251998
0.8468	Intermediate Similarity	NPC471089
0.8468	Intermediate Similarity	NPC141215
0.8468	Intermediate Similarity	NPC190065
0.8462	Intermediate Similarity	NPC275675
0.8448	Intermediate Similarity	NPC258592
0.8448	Intermediate Similarity	NPC178548
0.8443	Intermediate Similarity	NPC102316
0.8443	Intermediate Similarity	NPC100390
0.8443	Intermediate Similarity	NPC254614
0.843	Intermediate Similarity	NPC264192
0.8407	Intermediate Similarity	NPC193948
0.8407	Intermediate Similarity	NPC90769
0.8407	Intermediate Similarity	NPC472002
0.84	Intermediate Similarity	NPC140045
0.84	Intermediate Similarity	NPC295885
0.84	Intermediate Similarity	NPC596
0.8393	Intermediate Similarity	NPC100908
0.8378	Intermediate Similarity	NPC94942
0.8376	Intermediate Similarity	NPC478051
0.8376	Intermediate Similarity	NPC107338
0.8376	Intermediate Similarity	NPC109607
0.8374	Intermediate Similarity	NPC168879
0.8364	Intermediate Similarity	NPC102352
0.8362	Intermediate Similarity	NPC240509
0.8348	Intermediate Similarity	NPC474046
0.8348	Intermediate Similarity	NPC470628
0.8348	Intermediate Similarity	NPC259306
0.8333	Intermediate Similarity	NPC285091
0.832	Intermediate Similarity	NPC243014
0.8319	Intermediate Similarity	NPC157476
0.8319	Intermediate Similarity	NPC472003
0.8305	Intermediate Similarity	NPC241310
0.8305	Intermediate Similarity	NPC278163
0.8305	Intermediate Similarity	NPC169727
0.8305	Intermediate Similarity	NPC187950
0.8305	Intermediate Similarity	NPC47567
0.8305	Intermediate Similarity	NPC412
0.8305	Intermediate Similarity	NPC194310
0.8305	Intermediate Similarity	NPC258789
0.8305	Intermediate Similarity	NPC258815
0.8305	Intermediate Similarity	NPC131841
0.8304	Intermediate Similarity	NPC474242
0.8293	Intermediate Similarity	NPC6274
0.8293	Intermediate Similarity	NPC254146
0.8293	Intermediate Similarity	NPC33378
0.8291	Intermediate Similarity	NPC473920
0.8291	Intermediate Similarity	NPC476529
0.8291	Intermediate Similarity	NPC279143
0.8291	Intermediate Similarity	NPC268958
0.8291	Intermediate Similarity	NPC127530
0.8291	Intermediate Similarity	NPC475775
0.8276	Intermediate Similarity	NPC27999
0.8276	Intermediate Similarity	NPC477116
0.8261	Intermediate Similarity	NPC117712
0.8261	Intermediate Similarity	NPC247069
0.8261	Intermediate Similarity	NPC470919
0.8261	Intermediate Similarity	NPC469877
0.8261	Intermediate Similarity	NPC243354
0.825	Intermediate Similarity	NPC30188
0.825	Intermediate Similarity	NPC177820
0.825	Intermediate Similarity	NPC473255
0.8246	Intermediate Similarity	NPC302146
0.8235	Intermediate Similarity	NPC471965
0.823	Intermediate Similarity	NPC474567
0.823	Intermediate Similarity	NPC210005
0.823	Intermediate Similarity	NPC85391
0.822	Intermediate Similarity	NPC251226
0.8205	Intermediate Similarity	NPC106644
0.8198	Intermediate Similarity	NPC292588
0.819	Intermediate Similarity	NPC179626
0.8182	Intermediate Similarity	NPC275583
0.8182	Intermediate Similarity	NPC225049
0.8174	Intermediate Similarity	NPC194273
0.8174	Intermediate Similarity	NPC320118
0.8174	Intermediate Similarity	NPC33360
0.8174	Intermediate Similarity	NPC477266
0.8174	Intermediate Similarity	NPC194100
0.8167	Intermediate Similarity	NPC202666
0.8167	Intermediate Similarity	NPC471961
0.8167	Intermediate Similarity	NPC262199
0.8167	Intermediate Similarity	NPC471964
0.8167	Intermediate Similarity	NPC14617
0.8158	Intermediate Similarity	NPC471243
0.8151	Intermediate Similarity	NPC470921
0.8151	Intermediate Similarity	NPC4021
0.8151	Intermediate Similarity	NPC159456
0.8142	Intermediate Similarity	NPC310546
0.8142	Intermediate Similarity	NPC141350
0.8136	Intermediate Similarity	NPC319570
0.8136	Intermediate Similarity	NPC230513
0.8125	Intermediate Similarity	NPC166993
0.812	Intermediate Similarity	NPC309433
0.812	Intermediate Similarity	NPC55296
0.812	Intermediate Similarity	NPC58662
0.8115	Intermediate Similarity	NPC470780
0.8115	Intermediate Similarity	NPC470882
0.8108	Intermediate Similarity	NPC475036
0.8099	Intermediate Similarity	NPC469841
0.8099	Intermediate Similarity	NPC469842
0.8099	Intermediate Similarity	NPC471962
0.8099	Intermediate Similarity	NPC7850
0.8099	Intermediate Similarity	NPC6615
0.8099	Intermediate Similarity	NPC471963
0.8099	Intermediate Similarity	NPC247315
0.8087	Intermediate Similarity	NPC205534
0.8087	Intermediate Similarity	NPC269530
0.8083	Intermediate Similarity	NPC65858
0.8083	Intermediate Similarity	NPC235438
0.8083	Intermediate Similarity	NPC222688
0.8083	Intermediate Similarity	NPC107966
0.8083	Intermediate Similarity	NPC249848
0.8083	Intermediate Similarity	NPC40775
0.8073	Intermediate Similarity	NPC472972
0.807	Intermediate Similarity	NPC320383

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 NPC323821 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	2127
0.2-0.3	3885
0.3-0.4	1777
0.4-0.5	620
0.5-0.6	245
0.6-0.7	144
0.7-0.8	92
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.822	Intermediate Similarity	NPD6319	Approved
0.8167	Intermediate Similarity	NPD8328	Phase 3
0.812	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8053	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6373	Approved
0.7826	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6372	Approved
0.7805	Intermediate Similarity	NPD7492	Approved
0.7778	Intermediate Similarity	NPD8297	Approved
0.7769	Intermediate Similarity	NPD6059	Approved
0.7769	Intermediate Similarity	NPD6054	Approved
0.776	Intermediate Similarity	NPD7736	Approved
0.7759	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6616	Approved
0.7719	Intermediate Similarity	NPD5739	Approved
0.7719	Intermediate Similarity	NPD7128	Approved
0.7719	Intermediate Similarity	NPD6675	Approved
0.7719	Intermediate Similarity	NPD6402	Approved
0.7712	Intermediate Similarity	NPD4632	Approved
0.7705	Intermediate Similarity	NPD6015	Approved
0.7705	Intermediate Similarity	NPD6016	Approved
0.7692	Intermediate Similarity	NPD6650	Approved
0.7692	Intermediate Similarity	NPD6649	Approved
0.768	Intermediate Similarity	NPD8293	Discontinued
0.768	Intermediate Similarity	NPD7078	Approved
0.7652	Intermediate Similarity	NPD5701	Approved
0.7652	Intermediate Similarity	NPD5697	Approved
0.7642	Intermediate Similarity	NPD6370	Approved
0.7642	Intermediate Similarity	NPD5988	Approved
0.7586	Intermediate Similarity	NPD6899	Approved
0.7586	Intermediate Similarity	NPD7320	Approved
0.7586	Intermediate Similarity	NPD6881	Approved
0.7521	Intermediate Similarity	NPD6009	Approved
0.7521	Intermediate Similarity	NPD6014	Approved
0.7521	Intermediate Similarity	NPD6013	Approved
0.7521	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD6882	Approved
0.7458	Intermediate Similarity	NPD6883	Approved
0.7458	Intermediate Similarity	NPD7102	Approved
0.7458	Intermediate Similarity	NPD4634	Approved
0.7458	Intermediate Similarity	NPD7290	Approved
0.7436	Intermediate Similarity	NPD6011	Approved
0.7422	Intermediate Similarity	NPD7319	Approved
0.7419	Intermediate Similarity	NPD5983	Phase 2
0.7419	Intermediate Similarity	NPD6921	Approved
0.7395	Intermediate Similarity	NPD8130	Phase 1
0.7395	Intermediate Similarity	NPD6847	Approved
0.7395	Intermediate Similarity	NPD6869	Approved
0.7395	Intermediate Similarity	NPD6617	Approved
0.7302	Intermediate Similarity	NPD7604	Phase 2
0.7265	Intermediate Similarity	NPD6008	Approved
0.7257	Intermediate Similarity	NPD4755	Approved
0.725	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7115	Discovery
0.7209	Intermediate Similarity	NPD6033	Approved
0.7203	Intermediate Similarity	NPD6412	Phase 2
0.7193	Intermediate Similarity	NPD5696	Approved
0.7188	Intermediate Similarity	NPD7507	Approved
0.7188	Intermediate Similarity	NPD6336	Discontinued
0.7154	Intermediate Similarity	NPD6274	Approved
0.713	Intermediate Similarity	NPD4696	Approved
0.713	Intermediate Similarity	NPD4700	Approved
0.713	Intermediate Similarity	NPD5286	Approved
0.713	Intermediate Similarity	NPD5285	Approved
0.7105	Intermediate Similarity	NPD6083	Phase 2
0.7105	Intermediate Similarity	NPD6084	Phase 2
0.7105	Intermediate Similarity	NPD7902	Approved
0.7043	Intermediate Similarity	NPD4225	Approved
0.7018	Intermediate Similarity	NPD4697	Phase 3
0.7009	Intermediate Similarity	NPD5211	Phase 2
0.7009	Intermediate Similarity	NPD5226	Approved
0.7009	Intermediate Similarity	NPD5224	Approved
0.7009	Intermediate Similarity	NPD4633	Approved
0.7009	Intermediate Similarity	NPD5225	Approved
0.7	Intermediate Similarity	NPD6686	Approved
0.6991	Remote Similarity	NPD5282	Discontinued
0.6991	Remote Similarity	NPD7748	Approved
0.6984	Remote Similarity	NPD7101	Approved
0.6984	Remote Similarity	NPD7100	Approved
0.6975	Remote Similarity	NPD4768	Approved
0.6975	Remote Similarity	NPD4767	Approved
0.6964	Remote Similarity	NPD7515	Phase 2
0.696	Remote Similarity	NPD6317	Approved
0.6949	Remote Similarity	NPD5174	Approved
0.6949	Remote Similarity	NPD5175	Approved
0.693	Remote Similarity	NPD5695	Phase 3
0.6923	Remote Similarity	NPD5223	Approved
0.6923	Remote Similarity	NPD1700	Approved
0.6909	Remote Similarity	NPD3573	Approved
0.6905	Remote Similarity	NPD6335	Approved
0.6905	Remote Similarity	NPD6313	Approved
0.6905	Remote Similarity	NPD6314	Approved
0.6891	Remote Similarity	NPD5141	Approved
0.6875	Remote Similarity	NPD6908	Approved
0.6875	Remote Similarity	NPD8513	Phase 3
0.6875	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8517	Approved
0.6875	Remote Similarity	NPD8515	Approved
0.6875	Remote Similarity	NPD8516	Approved
0.6875	Remote Similarity	NPD6909	Approved
0.687	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5222	Approved
0.687	Remote Similarity	NPD5221	Approved
0.686	Remote Similarity	NPD4729	Approved
0.686	Remote Similarity	NPD4730	Approved
0.685	Remote Similarity	NPD7516	Approved
0.6842	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7900	Approved
0.6818	Remote Similarity	NPD3618	Phase 1
0.681	Remote Similarity	NPD5173	Approved
0.6807	Remote Similarity	NPD4754	Approved
0.6786	Remote Similarity	NPD5328	Approved
0.6772	Remote Similarity	NPD7328	Approved
0.6772	Remote Similarity	NPD7327	Approved
0.6754	Remote Similarity	NPD6399	Phase 3
0.6752	Remote Similarity	NPD7638	Approved
0.6748	Remote Similarity	NPD5249	Phase 3
0.6748	Remote Similarity	NPD5247	Approved
0.6748	Remote Similarity	NPD5248	Approved
0.6748	Remote Similarity	NPD5250	Approved
0.6748	Remote Similarity	NPD5251	Approved
0.6746	Remote Similarity	NPD6868	Approved
0.6741	Remote Similarity	NPD6845	Suspended
0.6721	Remote Similarity	NPD5128	Approved
0.672	Remote Similarity	NPD8133	Approved
0.6696	Remote Similarity	NPD5737	Approved
0.6696	Remote Similarity	NPD6672	Approved
0.6695	Remote Similarity	NPD7640	Approved
0.6695	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD6079	Approved
0.6638	Remote Similarity	NPD4629	Approved
0.6638	Remote Similarity	NPD5210	Approved
0.6637	Remote Similarity	NPD4753	Phase 2
0.6615	Remote Similarity	NPD8378	Approved
0.6615	Remote Similarity	NPD8296	Approved
0.6615	Remote Similarity	NPD8380	Approved
0.6615	Remote Similarity	NPD8335	Approved
0.6615	Remote Similarity	NPD7503	Approved
0.6615	Remote Similarity	NPD8379	Approved
0.6609	Remote Similarity	NPD4202	Approved
0.6593	Remote Similarity	NPD5956	Approved
0.6583	Remote Similarity	NPD7632	Discontinued
0.6565	Remote Similarity	NPD8080	Discontinued
0.656	Remote Similarity	NPD5215	Approved
0.656	Remote Similarity	NPD5216	Approved
0.656	Remote Similarity	NPD5217	Approved
0.6542	Remote Similarity	NPD3617	Approved
0.6538	Remote Similarity	NPD8377	Approved
0.6538	Remote Similarity	NPD8294	Approved
0.6522	Remote Similarity	NPD8034	Phase 2
0.6522	Remote Similarity	NPD8035	Phase 2
0.6504	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6334	Approved
0.65	Remote Similarity	NPD6333	Approved
0.6496	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD8074	Phase 3
0.6491	Remote Similarity	NPD6904	Approved
0.6491	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6101	Approved
0.6491	Remote Similarity	NPD6673	Approved
0.6491	Remote Similarity	NPD6080	Approved
0.6491	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD8033	Approved
0.648	Remote Similarity	NPD5135	Approved
0.648	Remote Similarity	NPD5169	Approved
0.648	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5127	Approved
0.6429	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD6067	Discontinued
0.6379	Remote Similarity	NPD5693	Phase 1
0.6378	Remote Similarity	NPD6053	Discontinued
0.6372	Remote Similarity	NPD7521	Approved
0.6372	Remote Similarity	NPD6409	Approved
0.6372	Remote Similarity	NPD5330	Approved
0.6372	Remote Similarity	NPD7146	Approved
0.6372	Remote Similarity	NPD6684	Approved
0.6372	Remote Similarity	NPD7334	Approved
0.6364	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6371	Approved
0.6339	Remote Similarity	NPD3665	Phase 1
0.6339	Remote Similarity	NPD3666	Approved
0.6339	Remote Similarity	NPD3133	Approved
0.6336	Remote Similarity	NPD4522	Approved
0.6325	Remote Similarity	NPD5778	Approved
0.6325	Remote Similarity	NPD5779	Approved
0.632	Remote Similarity	NPD5168	Approved
0.6312	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD3667	Approved
0.6293	Remote Similarity	NPD5692	Phase 3
0.6293	Remote Similarity	NPD46	Approved
0.6293	Remote Similarity	NPD6698	Approved
0.6283	Remote Similarity	NPD1694	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